Jacob Warwick's Playbook for Negotiating Executive Compensation
Lenny's Podcast
Jacob Warwick is a professional negotiator who works behind the scenes for senior tech executives, professional athletes, and Hollywood talent. Host Lenny Rachitsky says he has helped clients secure more than $1 billion in additional compensation. He rarely gives interviews and isn't on social media. In this conversation, Lenny admits he has always been nervous and bad at negotiating his own pay, and asks Jacob how people should approach it.
Jacob's answer is consistent throughout. Negotiation is less about confrontation than about information, timing, and collaboration. It starts long before an offer arrives, and it works best when a candidate treats the hiring process like an enterprise sale instead of an interrogation.
How much people leave on the table
Lenny opens by asking how much money people forfeit when they don't negotiate at all. Jacob says that even a mild, non-aggressive pushback, "What's the chance there could be a little bit more here?", almost always produces about a 20% improvement in his experience. He says this holds across levels. A $100,000 offer could become $120,000 from that one question, and he has seen the same roughly 20% bump, sometimes more, on million-dollar W-2 offers.
With his clients, Jacob says he aims for about 40% movement on average. He reports seeing increases of 100% to 400% over initial offers in some cases, most notably when salary bands were broken. Jacob argues people treat those bands "as gospel," and that people who challenge authority "in a meaningful and collaborative way" win more than those who don't.
He also observes a pattern by function. In his experience, product leaders, engineers, and designers, whom he describes as more introverted and thoughtful, negotiate worse than more extroverted marketers and revenue leaders. He calls this frustrating, given how much product has defined the tech era. He says he doesn't mean it as a knock on marketers, only that different sides of a business tend to negotiate differently. Lenny's admission that he struggled with this, Jacob says, should reassure listeners that they aren't alone.
Why asking isn't greedy
Lenny raises the most common fear. People worry they'll come across as greedy, that the offer will collapse, or that colleagues will see them as the person who pushed and will expect more of them.
Jacob's first response is about the value exchange. A company typically extracts far more value from an employee than it pays, which he puts at "5:1, 10:1, 100:1." Product people in particular build things with near-infinite scalability. Measured against what the company earns, he argues, asking for more isn't greedy. If you understand that exchange, you can have the conversation with confidence.
He doesn't claim this is risk-free. He acknowledges the danger of being a "tall poppy." But he says he would rather clients over-negotiate, reach a couple of rungs up the ladder, and get slapped down, because they are still "failing forward." He also says the goal isn't to push for the top of the band just because you can. If someone finds work that feels like play and is paid well, that matters too. His broader point is that the path to wealth runs through ownership, and a heavily taxed W-2 employee has good reason to push a little.
What founders and hiring managers should take from this
Lenny notes that many listeners are founders or hiring managers who may not welcome advice that helps candidates push harder. Jacob says he would challenge them too. He asks how much they prioritize attracting and keeping top talent, given how fast innovation is moving, and points out how expensive it is to replace people who leave.
He calls it a myth that negotiation has to be adversarial. His version is collaborative. The candidate asks the founder what matters to them and what value the work will drive, and terms follow from that. Often, he says, the way his clients break compensation limits isn't a bigger base or bonus percentage but performance incentives and milestone triggers. His example: if the company reaches $100 million ARR and the candidate contributed to that, is there another tranche of stock or a cash payment?
Jacob says he once found it hard to advocate for this, and as a former founder and CEO he understands why companies resist it. It is hard to structure, and "everyone thinks they're top talent." But he says people who are confident enough to push for performance-based pay tend to have more skin in the game and want to stay for the outcome, which is who he would want working for him.
He says he has started advising compensation committees at a couple of Fortune 500 companies and some large recruiting and talent consulting firms on getting more creative with pay structures so they don't lose people. Nobody wins, he argues, when a top performer leaves after ten months. The recruiting firm loses its performance fee, and the company pays to replace the person, which he says usually costs hundreds of thousands and, in some Fortune 500 cases, millions or tens of millions in lost IP.
Jacob mentions that he has negotiated against several past podcast guests on behalf of people they were hiring. Without naming anyone, he describes a recent Fortune 500 case with more than $10 million in compensation increases across a handful of people. By his account, the alternative was losing them to competitors after the CEO had made public announcements on earnings calls, and the stock dropping. The increase may have cost $10 million, he says, but it saved "300 plus, 300 500," and "almost anybody would pay 10 to save 300."
Working "fingerprintless"
Jacob describes his role as "fingerprintless." Unlike Hollywood, where agents negotiate on a client's behalf, corporate America has no common norm of third-party representation. Jacob thinks that might change as AI researchers sign $100 million contracts. For now, he says, an intermediary would dilute the executive's leadership and presence.
So he works like an attorney whose name never appears. All correspondence passes through him before it reaches the other side. Before a client talks to a CEO, they call Jacob, plan the approach, then the client has the conversation and they debrief. When the CEO sends an email, the client and Jacob draft the reply together. He says he usually tests the client's instincts first before polishing the language, because "every step of the way is a negotiation."
This deliberately slows things down. Jacob says "too hasty equals risk." Taking a couple of days to respond isn't meant to be belligerent or to manufacture urgency. He says it signals some scarcity and thoughtfulness, and it gives time to collect information.
The biggest mistakes: starting too late and hiding behind email
Asked for the single most common mistake, Jacob says people don't understand when negotiation starts. It starts much earlier than they think. A LinkedIn profile or résumé is a snapshot of the past and does nothing for your future positioning. If someone sees only "product manager," that is how they'll classify you, no matter how much you've grown. Headshots, profile text, and public narrative all shape perception. He half-jokes that he could once estimate someone's pay from the quality of their headshot, and that it was "wildly consistent." His principle: "If you are positioned as a commodity, you will be treated like a commodity." Sharing less publicly is often better, he says, because on a call you can correct the narrative instead of living with "the sins of what you did 10 years ago."
The same applies to recruiters, who take notes. If you tell a recruiter $225,000 sounds fair, Jacob says, they may call five years later expecting the same number and not recognizing how much you've grown.
The second mistake is hiding behind the easiest channel, usually email, because pushing back feels confrontational. The problem is that you can't control tone or timing. His example is a CEO reading a carefully worded pushback while angry in an airport security line and taking away only "That bastard wants more money." A video call, or ideally an in-person meeting, lets you convey tone, read body language, and correct course as you go. Later he adds that on a video call you might notice the other person is visibly exhausted and offer to reschedule, which email doesn't allow.
The third mistake is negotiating through recruiters. Jacob compares it to a game of telephone. You explain your position carefully, and the recruiter tells the CEO the same "that bastard wants more money." He says you have to negotiate with whoever has skin in the game and controls the P&L or EBITDA, and understand what motivates them. Going around the recruiter has to be done respectfully and planned. His general view: "just because it's uncomfortable doesn't mean you don't need to do it. It just means you don't know how to do it."
Home-field advantage and controlling time
Jacob says that at senior levels, "more deals are closed on the golf course than they are in a boardroom." He calls this home-field advantage. Walking into a company's office puts you out of your element, so where possible he likes moving the conversation elsewhere.
People also fail to control when conversations happen. If a CEO wants to meet at 6:00 a.m., Jacob suggests knowing your own best hours, for example 10 a.m. to 1 p.m., and saying you're unavailable until then. He argues this signals scarcity and that you won't be pushed around, which creates a "rubber band effect" that makes you more attractive.
His example involves clients interviewing for C-suite roles at OpenAI, where he says conversations with Sam Altman happened on walks through downtown San Francisco instead of in the office. Jacob's reading is that walking side by side instead of sitting across a table changes body language and energy. You are solving a problem together, "almost like you could put your arm around the other person." He says he later learned the practical reason: OpenAI didn't want executives coming into the office because it was so chaotic.
Lenny asks whether this is realistic for everyone. Jacob concedes that a product manager talking to a director may not be able to pull them out of the office, and that his examples are C-suite situations where deals sometimes close over drinks at 8:30 p.m. Still, he says, suggesting a walk doesn't hurt, and doing so can build a stronger relationship.
Responding to an offer, step by step
Lenny asks what to do when an offer arrives, say $300,000 plus equity. Jacob's first step is gratitude and enthusiasm: thank them, say you're excited to work together, and say you'll review it over the next couple of days with your spouse or an advisor. At senior levels, he says, it's expected that five or six people, including an employment lawyer and a coach, will review an offer. The key is to "sell that the deal is going to be done," even if you're unsure, so any ask later doesn't seem egregious.
Then, perhaps three days later and ideally in person or over a walk, he might have the candidate say something like: "I've got to be honest with you, where this offer stands right now, I don't feel comfortable moving forward. It's a little lighter than I expected." Then wait. If they ask what the candidate had in mind, he suggests turning it around: what does the range look like, and what performance is expected at each level? If they say the offer sits mid-range, ask what the top looks like and what it would take to get there.
He also describes over-leveling. After 2021, he says, C-suite executives are going back to VP roles and VPs back to director roles, especially when moving to larger companies. A line his clients use is that they are "likely a little more horsepower than you anticipated," followed by asking whether the comp could be restructured for that level of talent. He reports three cases last year that began in the $185,000–$285,000 range and ended around $1.1 million, with larger stock and cash, and two deals offered at $600,000 that landed at $1.1 million and $1.2 million. In those cases, he says, roles that began at senior director were up-leveled to VP because the companies were reaching for top talent. He acknowledges that less experienced listeners may not be in that position, and says a natural 20% ask is still worth making.
Anchoring, and the cost of splitting the difference
Asked whether "what's the chance there's a bit more? I was expecting X" is his standard line, Jacob qualifies it. For very senior people he usually avoids re-anchoring with a number. He cites a line he attributes to Chris Voss: you should never be so sure of what you're worth that you wouldn't accept more. Once you state a number, he says, it becomes the ceiling, and the other side naturally wants to split the difference.
His illustration is a Hollywood writer offered $700,000. The writer's attorneys, described to Jacob as the most aggressive in Los Angeles, countered at $1.3 million, and the studio settled at $1 million, right in the middle. Jacob's question is whether a $1.5 million ask would have landed at $1.1 million, or $1.7 million at $1.2 million. His view is that the attorneys weren't aggressive enough, and he calls it "lazy negotiating." Everyone was happy, the client, the attorneys, and the agency collecting 10%, but no one found the ceiling. If a film might make $50 million, he asks, why not add milestones tied to its performance? He compares this to Tom Brady's Tampa Bay contract as he describes it, with incentives for eight wins, twelve wins, playoffs, a division title, the Super Bowl, and Super Bowl MVP.
He later gives a severance example of not splitting the difference. A chief revenue officer had a $350,000 base and $350,000 bonus, $700,000 in on-target earnings. They agreed on severance of six months of on-target earnings, but the paperwork came back specifying six months of base salary, cutting the amount in half. The client's instinct was to propose meeting in the middle. Jacob told him instead to ask simply whether it was a mistake. The CEO said it must have been and told him to redline it. Jacob says the client was fired twelve months later and recovered $350,000 over six months, money he would have partly given up by splitting the difference.
Who should name a number first
On the "what's your comp expectation?" question, Jacob says the pressure to answer is usually stronger early in a career, and a recruiter pushing hard for a number signals they're looking for a more price-sensitive hire. That can be fine, he says, and sharing a number early or mid-career can still produce a good outcome. But things change higher up. Top recruiters, in his experience, don't ask about comp at all. They focus on value creation, but they only reach out once you are well known. Nine out of ten recruiters will ask for a number.
His suggested response is roughly: "I don't talk about compensation until we're ready to make an offer. It sounds like we're pretty far away there. I'd love the opportunity to learn more about the team, understand where the value comes in… Is that going to be a problem?" If they insist, he suggests saying you're uncomfortable because you don't yet understand the scope of the role, and asking what they had in mind. He notes that Americans in particular struggle to say no, and that people from some other cultures can be more direct.
He learned this from his own career. As a marketing manager at Series A companies in San Francisco he made $12 an hour without realizing how little that was, then was promoted to director at $14 an hour. When he saw marketing directors earning around $110,000, he stopped disclosing his pay. When a recruiter called, he asked what they had in mind, heard $110,000–$130,000, and said he was at the upper end of that. He says he went from $14 an hour to $120,000 a year in one jump, which he calls life-changing. He adds that he hated marketing work and thought more money would fix that, which "turns out that was a fool's errand."
Power, need, and the risk of saying no
Lenny asks whether deals fall apart when people refuse to give a number. Jacob frames the answer around power. If you can say no, you have "infinite power." That changes when you're unemployed with a mortgage, and he says he doesn't shame anyone who gives a number to get hired. He notes that being out of work for six weeks in San Francisco can mean homelessness. That's why, he says, people negotiate more confidently while employed. Unemployment also strips people of the job title that Americans treat as identity, and the urge to end that pain makes people give in to authority. Money to wait and practice with difficult conversations both increase power, he says.
If a company disrespects you for a simple pushback, Jacob says, that tells you how it will treat you. He also describes a tactic of giving someone a positive reputation to live up to, whether they deserve it or not. For example: "I want to thank you for being an advocate for me and for respecting that I won't share compensation figures right now." The recruiter then has to either reject that description or go along with it.
He also recommends continuing interview processes that look underpaid, as practice and because you can always decline later. If the role is really more senior than the pay, you can offer to introduce the company to someone who fits better. Sometimes, he says, the company decides it wants the more senior role. His own first VP job came out of turning down a $70,000 content manager position. Six months later, after what he calls a long negotiation, he landed a VP role at about a quarter million.
Selling the vacation: interviewing as discovery
Lenny identifies what seems to be the core of Jacob's philosophy: stop benchmarking yourself against a role and show the company what pain you will solve. Jacob says it starts with curiosity. When he asks a room of 400 people who actually does the job in their job description, nobody raises a hand, because real roles contain much more than the description. That's another reason not to anchor early. He describes scope creep: a candidate names a senior PM number, the interviews reveal a director-level role with five reports, a product-led growth motion, and an engineering pod, and then the offer comes in 20% below the original number. When the candidate asks for director pay, the company says, "But you said you only wanted 140."
He wants product, engineering, and design people to treat interviews like enterprise B2B sales. Selling a $1.5 million product to Salesforce might take 18 months of building champions and understanding what each stakeholder values, and you wouldn't pitch the price at the start. He says "tell me about yourself" interviews keep candidates on the back foot, revealing information and getting none back. Instead, he suggests asking whether the interview could feel more like a consultation or brainstorming session, then working through a sequence:
- Why am I here? What excites you about me?
- Labeling: "It sounds like you have a challenge with this product line… Is there anything that I missed?"
- What have you done about it, and how big a problem is it? He compares this to a SWOT analysis: what went well, where the team failed, what you should be doing, and what shouldn't be touched.
- "Selling the vacation": imagine six months from now, the problem is solved and two launches are done. "When you head into that board meeting next, how can we ensure that your head is held high?"
Jacob says the aim is to walk the hiring manager from pain to a relieved future in which the candidate stands beside them. By the offer stage, he argues, there may be five other PMs, but the manager can only picture working with this one, so pushback is much more likely to break the rules.
His story here involves a director who had made a documentary for a very famous musician's billion-dollar tour. Every agency wanted to sign this director, who wanted to move into feature films. Jacob's client, an agent, was relying on name-dropping past clients such as Julia Roberts and Matt Damon. Jacob saw that as a problem, because "if we're leaning on logic and credibility, we're losing." He asked who the agent would introduce the director to if the deal were already signed, and had them schedule that meeting in advance. When the director asked why they should sign, the agent asked what they were doing Friday, because lunch had been cleared with Steven Spielberg. By Jacob's account, the response amounted to "where do I sign?"
Lenny summarizes this as understanding the landscape, showing where you add value, and helping the company picture the solved state. Jacob adds that people struggle to see their own value because they're too close to it. Product people who stay in a product bubble may not see their impact on marketing, and breaking limits requires understanding how your work affects other functions and what motivates them.
Planting seeds, reciprocity, and controlling the narrative
Jacob describes his own business practices as examples. On calls with prospective clients, he sometimes sends two or three introductions while still on the phone, for example to someone in product at Google. He says this creates a reciprocity imbalance and gives him several contacts who can later give him a fuller picture of the person or nudge them to sign.
He then role-plays with Lenny, asking what would make this the best episode of the year and what commenters would say. Lenny says that to an outsider this might sound manipulative, but that as the recipient he loves the question because it focuses on his goal. Jacob explains that he plants the words he wants people to repeat, asking, for instance, whether someone will tell a friend he was helpful or something unflattering, so the only natural answer is the positive one. He acknowledges some listeners may find this manipulative and says he hopes people "use this for good and not evil," but that "this is just the way power works." He compares it to calling your references before a reference check.
In interviews, he suggests asking for feedback live instead of waiting for a rejection email: what will you tell the committee, is this a "slam dunk," what should I have asked, where did other candidates do better? If the answer isn't good, propose a follow-up conversation to address it.
When Lenny imagines telling a hiring manager "I'm going to solve churn, fix onboarding, level up design," Jacob adds a caution. You have to deliver, and failing to will haunt your reputation. He also wouldn't be so sure onboarding is the real problem yet. Dragging out the process and resisting manufactured urgency lets you learn more, for example whether the product might be deprecated because of AI, which would make fixing onboarding the wrong priority. His rule: "Under promise, over deliver. Always." To founders, he says his goal isn't to take a bigger slice of their pie but to expand the pie with candidates whose pay is tied to results.
Confidence as a hype man, and positioning yourself like a product
Asked how he helps clients feel confident they're worth more, Jacob says part of his job is being a hype man. Many clients are extremely successful, and he reminds them their decisions have put them among the top earners on the planet. He also reframes the job search in each client's professional language. For sales leaders it's an enterprise sale. For marketers it's positioning and market research, where inbound leads close more easily than outbound. For product people it's a PRD: interview the customer (the hiring manager, CPO, or CEO), understand their needs, design a solution, and remove friction.
He tells introverted product people not to imitate him. He describes himself as a "6'3" tall white dude in California" with a sales persona and says they should "be you, your authentic you." Early attempts will feel as rough as early PRDs and slow sprints did, he says, but become second nature over time.
He emphasizes making the process frictionless for the interviewer by leading the conversation, which reduces their cognitive load while he collects information and reveals nothing about comp. He cautions that this isn't a "miracle drug." Some companies simply lack budget, but the company has to want you before you have leverage. He also suggests asking an interviewer to coach you on the next person you'll meet (his hypothetical is Marc Andreessen), because coaches want their players to succeed. This lets you bring that coaching into the next conversation and suggest other stakeholders to meet, such as heads of engineering, marketing, and sales, while controlling scarcity by saying you're not available until Thursday. That is how the standard 20% becomes 40% or more, he says. If a client arrives with an offer already in hand, he might get them 40%. If they arrive earlier, he might have raised the initial offer by 40% before they knew it, and then pushed it further.
Individual contributors and information asymmetry
Lenny asks whether an IC product manager interviewing at Meta can realistically flip the conversation. Jacob says he's frustrated that ICs are often paid less than leaders. He says he once interviewed for a Meta IC role he describes as an "i9" at about $1.2 million a year, and that Meta was hiring former CEOs and around 150 growth PMs at that level. He doesn't think the approach differs for ICs. Whether you lead people or processes, you're a leader. He says taking ownership of the conversation doesn't mean steamrolling. It means controlling the one thing you can control, how you show up, with "assertiveness, not aggressiveness."
For an IC, he might ask how Meta values ICs compared with leaders. Once the interviewer says they're valued equally, and the offer later comes in about 30% below comparable leader pay according to benchmarking data or friends, the candidate can point to that statement, thank them for being an advocate, and ask whether the offer can be made more equitable. "Prove it. Or prove to me that you lied," he says.
When Lenny says a hiring manager might just say no, Jacob agrees that can happen. He says he's trying to open an emotional conversation, because you'll always lose a purely logical argument against a company that negotiates thousands of times a day while you negotiate four or five times in your career. He uses the party game Werewolf to explain this. The werewolves, a small minority who know each other's identities, win 60–70% of the time in his account even when outnumbered five or six to one, because they hold the information. Companies know what people earn, what they'll accept, and how budgets can change. He says it's easier for executives than for middle managers to push back, but that executives who claim there is no flexibility are the people who build those rules: "Humans built this. This is not concrete authority."
Jacob's tactical list
Asked for his top five tips, Jacob offers, somewhat loosely by his own admission:
- Never be so sure of your worth that you wouldn't accept more. Ideally no numbers are discussed until necessary, and you should know how to respond if the other side names one first.
- Never split the difference, as in the severance example above.
- Slow down. Haste equals risk, and patience gives you time to gather information and build your case.
- Use emotion, not just logic and credibility. Jacob cites Aristotle's ethos, pathos, and logos, adds kairos (timing), and says executives rely too much on logic and credibility because corporate life discourages authenticity. He mentions Chris Voss's "tactical empathy," admitting it sounds Machiavellian. One example: a woman negotiating with a female executive might thank her for being an advocate for women, and if the offer comes in below a man's, ask, "If you were in my shoes, what would you do?" Jacob calls that one of his favorite lines, especially when negotiations stall.
- Collaborate, don't confront. Picture putting an arm around the other person and whiteboarding a solution together instead of facing each other across a problem.
He adds "make it about we, not me" with a story about a chief marketing officer joining a $100–200 million private company. The CEO said every executive received identical terms: $340,000 base, 30% bonus, and the same equity. She was already getting a raise, so they went after severance protections instead. The CEO said the company had never offered severance. They reframed it: given talent poaching and a recent RIF, wouldn't it look good to proactively give the whole executive team six months of severance? They fed the idea to the CEO so the CEO looked like the hero, and she arrived as "the woman that negotiated us all severance protections." Jacob notes this is uncommon, especially with private equity.
His bonus tip is creativity. A CEO candidate had two offers, both at $2.4 million a year and both maxed out, and couldn't choose. Jacob jokingly asked what car she liked. When a company asked what it would take to hire her, she mentioned a company car, then Mercedes, then a G-Wagon. Jacob says the budgets were capped, but a roughly $350,000 vehicle over 6,000 lb could be written off by the company and reduced its tax expense, so it was added. He stresses listeners shouldn't expect this. The point is finding a solution at a stall point.
When things fall apart
Jacob says he has never had a client's offer rescinded. What he sees more often is a final take-it-or-leave-it ultimatum. He did take on, pro bono, the case of a CMO who wasn't his client and whose roughly $800,000 offer had been rescinded. Her career coach had told her to "negotiate like a white man," aggressively. She was negotiating with a female CEO and three other women on the leadership team, and they withdrew the offer because she seemed like a bad cultural fit. She told Jacob she had been uncomfortable with the advice but followed it because she believed women should push for themselves, and he commended her for that.
Jacob's advice was to call the CEO and explain honestly. She acknowledged that women should look out for each other, said she had hired a coach because she had failed to advocate for herself in the past, a feeling he expected the CEO to share, and admitted she had followed advice she disagreed with. According to Jacob, after two phone calls to plan it, the offer came back and she now earns $800,000 a year. His lesson is honesty, integrity, and "extreme ownership" when things go wrong, even if it means being reset a level.
No universal script
Asked whether he treats male and female clients differently, Jacob says he takes a different approach with every person, based on function, city, culture, gender, sexuality, race, and other factors. He describes speaking to about 400 women at Chief, the "scariest position" for him as a white man. An African-American woman asked whether they should just negotiate for 84% since that's what they'd get anyway. He acknowledged he doesn't know what that feels like, then asked the mothers of daughters in the room whether they could tell their daughters to aim for 80%. His broader message is to push back so that a rising tide raises all ships and the precedent rises for the people who come next.
He tells another "we" story about one of Lenny's newsletter readers, a CPO being pushed out in a private equity takeover. His CEO of ten years wouldn't help until Jacob pointed out that the CEO, who expected to be fired as well, would get two to three times whatever precedent he helped set. The CEO and CPO then built a plan together, and the CPO secured a retention bonus and severance.
Lenny says he had originally wanted a step-by-step guide, and Jacob had told him one doesn't really exist. Jacob explains that negotiation literature often feels intimidating and academic, whether it's hostage scenarios from Chris Voss or BATNA and ZOPA from Getting to Yes, and that focusing on frameworks makes people stop listening. He says curiosity and empathy matter most. If you hit a block and don't know why it exists, you haven't asked the right questions. Negotiation, he says, comes down to "information and timing. That's what creates power."
He says he is writing a book this year titled Predetermined, which he'd like to have a question mark, because outcomes aren't predetermined even if they're harder for some people. He likes asking clients who want something in five years what it would take to do it in one, and asking wealthy clients who say they need another $10–15 million what their life would look like with less.
To show that it isn't always about money, he describes a Marvel-scale franchise, which he estimates at $500 million to $1 billion, where an A-list actor had the original writer of the first two films fired, disliked the replacement even more, and caused months of delays. The agency offered the original writer an extra $1 million to return, but for someone earning about $10 million a year that 10% wasn't enough to repair the relationship. Jacob suggested the actor apologize, and he says the apology is what brought the writer back, saving the $1 million. He adds that he uses big numbers because they're striking, but that going from $18 to $24 an hour can be life-changing. He says he was homeless about 12 years ago and unsure he could afford gas.
Hollywood scale and the first move after an offer
Asked for another Hollywood story, Jacob describes an A-list actress offered $5 million for a film. Her attorney asked for $22 million. Within about two days the studio moved to $13 million and the attorney came down to $18 million, moving in $4 million chunks while, as he puts it, people in tech wonder whether they can get $10,000 more. He notes that a million seconds is about 11 days and a billion is about 31 years, to show how quickly the numbers scale, and concludes that to really raise your comp, you have to "move rooms" and build connections with people at that level.
For Lenny's final tactical question, what to do when a recruiter sends an offer, Jacob says there's probably about 20% of room. If you're re-anchoring, anchor high, because the recruiter will likely split the difference. He cites a negotiation study from the 1970s he read in which, as he recalls it, people who anchored "egregiously high" won 75% more than those who tried to be reasonable. Ask for $150,000 more and you might get $50,000–$70,000; ask for $50,000 and you might get $15,000. If you've already committed to a range, he suggests saying that after the conversations with the hiring manager the scope seems to have grown, and asking whether they're open to revisiting the comp structure. If the recruiter says that's the limit, text or email the hiring manager something short, such as that you're almost there, there's a sticking point, and whether they're open to a quick chat, without undermining the recruiter or sending a list of promises. He notes that Lenny replies to emails in two words, and says confidence tends to shorten communication, sometimes to just "Open to chat."
Why he does this, and his closing message
Jacob says he's booked up and not looking for clients. His mission is to make what he has learned from very successful people accessible without a paywall. He shares scripts, case studies, and a roughly eight-hour job search course he once sold for about $1,000 and now gives away free through his Substack, Execs and the City, and YouTube. He attributes his interest in power to a childhood marked by substance abuse and trauma in which he never felt safe. As an adult he recognized the same fight-or-flight responses in boardrooms, but found them far less scary because "it's just money." He says he has wanted to help people feel safe in tense moments ever since.
In the lightning round he recommends Robert Cialdini's Influence, Herb Cohen's You Can Negotiate Anything (which he calls dated but simple), John Lowry's Negotiation Made Simple, and Kim Scott's Radical Candor. He says the last one, together with his wife, taught him to be assertive. His motto is "Always give more than you expect to receive." He also describes his work on the board of a foundation in Bozeman, Montana, that helps rural Montanans access healthcare, connected to his son's cystic fibrosis diagnosis. He tells the story of a mother whose son died waiting for a lung transplant she couldn't afford, and whose younger son the foundation later helped by funding a life flight to Denver for surgery. He says the mother now feels guilt that she didn't know the foundation existed sooner.
His parting advice is to take a chance on yourself. Fights over pay are "first world problems" that won't cost you your home, having more lets generous people give more, and failing still means failing forward. He says he once despised wealth and distrusted people who had it, but that "if you fear it and you don't understand it, you'll never have an opportunity to change it." The goal, he says, isn't to copy his style or anyone else's but to find the approach that fits you.
What's the most common mistake that people make when they're negotiating their comp?
Often we'll hide behind the easiest communication channel possible. I might email you my demands. The problem with that is I can't control tone. If I push back and the CEO that reads it's in the airport security line and pissed off and they read it, they might be like, "That bastard wants more money."
A lot of people listening to this are just afraid to ask for more. I'm going to come across as greedy. It's all going to fall apart. But when you look at the money that the company's making in comparison, like you're not being greedy.
It doesn't have to be such an aggressive thing. It doesn't have to be confrontational. The simplest advice: "What's the chance there could be a little more?"
That's not greedy at all.
The core of your philosophy is make it very clear to the company here's the pain I will solve for you and here's why it's worth paying you this much more.
These companies have significant leverage over you. They know what people make, they know what others make, they know what they'll accept. You have to understand what value you can create and if you understand that value, you can have that conversation with confidence.
Today my guest is Jacob Warwick. Jacob is a professional negotiator. He works behind the scenes with his clients, mostly senior tech execs, professional athletes, and Hollywood celebrities. And he helps them navigate their most complex career negotiations, including their comp, their bonuses, and investments, also M&A and takeovers and enterprise sales deals and more. He's helped his clients secure over $1 billion in additional comp. And he's told me that he's negotiated against a number of guests on this podcast.
He is very much under the radar, is not on social media, rarely does interviews, and in this exclusive conversation, we get super deep on the specific tactics and psychology of comp negotiation, including why you should never negotiate over email, who should speak first when the question of comp comes up, the most common and costly mistakes that people unknowingly make when they're negotiating comp, and so much more. Jacob is also just a truly stellar human and I'm very excited to be sharing his story. Don't forget to check out lennysproductpass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. Let's get into it after a short word from our wonderful sponsors.
This episode is brought to you by Orkes, the company behind open-source Conductor, the orchestration platform powering modern enterprise applications. Modern systems are built on microservices, APIs, and event-driven architectures, but legacy automation tools can't keep up. Siloed low-code platforms, outdated process management, and disconnected API tooling break down under real-world scale and constant change.
Orkes Conductor provides a production-grade orchestration layer for coordinating microservices, APIs, data pipelines, human tasks, and agentic workflows with deterministic control flow, retries, observability, and governance. Built for enterprise scale, Orkes supports visual and code-first development with built-in compliance and reliability. Through a built-in MCP gateway, AI agents handle reasoning and decision-making while safely accessing existing APIs and internal systems as MCP tools. This enables agents to operate across enterprise environments and scale from demos to production, orchestrating systems, agents, and humans together to deliver smarter outcomes faster. Learn more at orkes.io/lenny. That's orkes.io/lenny.
This episode is brought to you by Mercury, radically different banking loved by over 300,000 entrepreneurs, including me. I switched to Mercury from Chase over a year ago, and it is such a profoundly better experience. It's like an actual product person built a bank versus a banking person building a product. It is fast, it's elegant, it is super easy to set wires, to track my spending, to set up triggers, to move money around when accounts get low. We moved all of our invoicing to Mercury, and it is such a smoother experience than anything else we've tried.
It's also really easy to grant people on your team just the right amount of access to help take work off your plate. It's free to get started. No in-person visits, no minimum balances. The product also flexes to all sizes of company, from startups to large enterprises. Just visit mercury.com to learn more and apply online in minutes. Mercury is a fintech company, not an FDIC insured bank. Banking services provided through Choice Financial Group and Column N.A., members FDIC.
Jacob, thank you so much for being here. Welcome to the podcast.
I'm very happy to be here and thank you for interfering with my sleep all week out of my excitement. Usually it's my newborn and toddler, but this time I was waking up at 3:00 in the morning thinking about it and it's going to be a great chat. So, I'm very excited. Thank you for having me.
I really appreciate that. It's going to be worth it. It's going to be worth it mostly to us to extract all this wisdom from your head. So, we're going to be going deep on negotiation. How to better negotiate for comp and this will translate into all kinds of other ways in your life beyond comp. This is something I personally have been very, very bad at in my career. Like I don't know if maybe one time I pushed back and negotiated a higher comp, but I've always been really nervous to do this and just really bad at this.
And I imagine most listeners are nervous and bad at this. And you do this for a living. You help people negotiate. Which I don't think people even know this is a thing that exists, that somebody's out there that can help you negotiate. And so, you've seen a lot of negotiations up close. Most of the people you work with, just as a context, are very senior people, but a lot of the stuff we're going to talk about is going to apply to anyone at any level.
Let me start with this question just to give people a frame of reference. How much comp are people generally leaving on the table when they don't even try to negotiate?
Yeah, so typically what I've seen is even without my help, just general pushbacks, not aggressive, a simple "What's the chance there could be more here?" kind of pushback. I mean, that's about as easy as it can get. You get the offer, you say, "What's the chance there's a little bit more?" Almost always see a 20% improvement on that. And that is across the board from earlier stage positions. Let's say they gave you a $100,000 offer, 120 could be there just from a simple push back, which is, when you're making that kind of money, that's life-changing, right?
I've noticed that when you make a million-dollar W-2, same push back, 20%, sometimes more, just on the what's the chance, depending on how well you're going to navigate that interview process. Now, on average, when I'm calculating out, what I'm looking for with clients is about 40% movement on an increase. We have seen as much as 100, 200, 300, 400% increases from initial offers. Most notably, breaking salary bands, which we all treat as gospel, which is something we'll probably talk about through the course of this podcast today. That, you know, those that challenge authority and challenge in a meaningful and collaborative way will win more than those that don't.
And what's interesting is I found that product leaders, engineers, designers, some of the more, tend to be more introverted and thoughtful types, negotiate more poorly than the obnoxious marketers and revenue leaders and the more extroverted types. And it's frustrating because if you look back at the last, say, 25 years or so, product has really defined the tech generation in so many ways. This isn't to discredit marketers or anything like that. It's just to show that there's a couple of sides of the business and everyone tends to negotiate a little differently.
So, you looking back at your career and say, you know, the great Lenny had a tough time pushing back. I think that's actually inspiring for a lot of the listeners to see that you're not alone in feeling this. It doesn't have to be such an aggressive thing. It doesn't have to be confrontational. The simplest advice that I can give you is, what's the chance there could be a little more?
That's not greedy at all. It's just a simple ask. And even that, 20, 30%. So again, a lot of people listening to this are just afraid to ask for more. There's like, I'm going to come across as greedy. It's all going to fall apart. They're going to be like, what are you talking about? No, no, forget it. Or, you know, they join, they get better comp, and then they're like, everyone kind of knows that I pushed all this and I'm this kind of greedy person. Now the expectations are higher. What do you tell people to help them get past that and actually negotiate and actually go for it?
Yeah, a couple things here. So first of all, usually a company is extracting much more value out of you. Naturally, like 5:1, 10:1, 100:1, right? I know the audience is primarily product here. I mean, you're developing products that have infinite scalability in some capacity.
That's going to make the company a lot of money, and they are a big piece of that.
And product tends to be rewarded fairly well, right? But when you look at the money that the company's making in comparison, like you're not being greedy. And if you understand that value exchange, you can have that conversation with confidence. That's not to say that being a tall poppy isn't risky. That's the term. You over negotiate. I would rather my clients over negotiate, reach a couple rungs up on the ladder, and they get slapped down. They're still failing forward, and they're growing in some capacity.
And if you can ideally align work that doesn't feel like work, it feels a little bit more like play, with strong compensation, you don't always need to negotiate hilariously for the top of the band or break the bands just because you can, right? This isn't to be greedy. Right? But it's just to understand that this value exchange isn't fair for you regardless of how it works. Like the path to wealth is through ownership, right? And as a W-2 employee, you're being taxed heavily. And it makes sense to push a little bit in this context. So, that's typically where I start. I want you to just have the confidence to know that it's okay.
Let me come at it from the other direction. A lot of people listening to this podcast are founders or hiring managers, managers. They may not be super excited to hear we're giving people advice on how to negotiate harder for higher comp. What could you say to them to make them feel a little bit better about us sharing this sort of advice?
So, I will challenge them as well. How important of a priority is top talent and maintaining and retaining top talent to you? Right? When you were thinking about how quickly the speed of innovation is happening. You've had a lot of great AI guests on the channel recently. Right? Like the exponential curve of growth is increasing. If you hope to stand a chance, you need to attract the top talent. And you need to keep that top talent cuz it's very expensive to replace them.
I'm not suggesting that people beat you up for the sake of beating you up. So, this is a myth about negotiation, that it's adversarial. What I teach is how can we be more collaborative? So, the conversation is, "Look, Lenny, as a founder, can you help me understand what's important to you? The value that this work will drive." And then naturally we'll come to terms that make a little bit more of a value exchange make sense there.
So, oftentimes some of the ways that we're breaking the boundaries of compensation isn't necessarily advocating for a busted base comp level and bonus percentage. Oftentimes we're putting performance incentives, milestone triggers. If the company grows to 100 million ARR and I contributed this to it, what would that outcome look like? Would that be another tranche of stock or would that be cash or would that, you know, we're getting more creative here.
And so, what's interesting is for the longest time I had a difficult time advocating for this. And having been a CEO and founder myself, I understand why you don't want to do it cuz it's hard. It's hard to make this. And everyone also thinks they're top talent. And when everyone thinks they're top talent, somebody's got to be lying. Right? It can be difficult to understand that. So, those that I found are more confident to push towards performance-based tend to have more skin in the game. Tend to want to stick around and see that success happen. Those are the types of people I want working for me if I want to be a very competitive organization.
I have started to have these conversations with a couple Fortune 500 companies as well as some talent consulting companies, think big recruiting firms, where they've brought me in to advise on the comp committees so that they can get more creative with their structure so they don't lose talent. Because nobody wins when you hire a top performer and they leave in 10 months. The recruiting firm loses their pay, right? Their performance pay. The company now has to go back and replace that person. It usually costs hundreds of thousands. And in some of the realms that we navigate in the Fortune 500, it will cost millions if not tens of millions to replace the lost IP there.
So, the argument here is it's okay to get creative. Reward it when you see it, right? I'm not suggesting give everyone everything I've been the company and totally ruin your business model. But, if you want to be competitive, be competitive with your pay as well.
That's a great answer. And we were chatting before we started recording this, and you shared that you've helped people negotiate with many of the guests on this podcast, like people that they were hiring, and you helped them get higher comp.
I won't mention any names. Some recently were in the realm of 10 million plus on increases in compensation across a team of just a handful of folks. Again, Fortune 500, but the alternative was lose them to competitors and have the stock drop after the CEO made announcements publicly in their earnings calls. And so, they don't know that it may have cost them 10 million today, but it saved them 300 plus, 300, 500 in this business process. So, the success will be there, and I would say almost anybody would pay 10 to save 300.
And the way you operate, just so people understand, is you're very behind the scenes. You work with clients, and you advise them. You're never involved in the negotiation. You just give them advice on how to approach it.
I would call it fingerprintless, and there's a reason for this. So, it's not yet popularized. Maybe it will be with some of these AI ICs and these hot scientists pulling down $100 million contracts. Maybe this will change soon. In Hollywood, you have an agent negotiate on your behalf, and they kind of are serving as that middle mediator. That's not common in corporate America right now, right? Now, if that happens, it almost dilutes the leadership and presence of the executive.
And so, how I work is similar to an attorney, where all correspondence goes through me before it goes to the end recipient. So, let's say that you're going to talk to the CEO, you call me first. We prepare the game plan, we strategize, you then perform, then we debrief. Then, the CEO sends you an email. That email comes to me, we draft it together. I usually test my client's instincts first, rather than just doing the work for them. Test their instincts, polish the language, because every step of the way is a negotiation.
Now, this also slows the process down. We want to go slower, and I'm sure we'll talk a little bit more about that in the podcast. Too hasty equals risk. So, as you slow down, oftentimes we want to take a couple of days to respond, not to be a jerk or belligerent or to manufacture some fake urgency, but it shows a little scarcity and thought process to your time and we get to
calculate and collect information through the process.
This is so interesting. What's the most common biggest mistake that people make when they're negotiating their comp?
They don't understand when it starts. So, it starts much sooner than you think. So, I've got myself in hot water with this before, too, because a LinkedIn profile and your resume is a snapshot of what you've been in the past, but it doesn't help you negotiate in the forward. Right? So, if somebody can say, "Oh, I'm looking at Lenny and I'm looking at product manager." If that's all they saw, they're not going to know all this work that you're doing in the future or moving forward and what your vision is, things like that. So, they stamp you as product manager Lenny. Right? Now, you're media mogul icon, whatever, right? But there's a gap that you have to fill.
Right? So, the things you say on LinkedIn serve as a perception. The headshot that you have serves as a perception. I used to joke that I could scan profiles, I would know how much money someone made by the quality of their headshot. And you can see, and it was wildly consistent. It was almost frustrating. But anyway, what you're putting out into the world, the narrative you share publicly, starts to become how you're known, your reputation.
If you are positioned as a commodity, you will be treated like a commodity. Right? So, oftentimes the less you share is better because when you're on the phone with somebody, you can correct the narrative and steer the conversation where you want it to go versus have to live by the sins of what you did 10 years ago as an example.
So, the things you share with recruiters, they take notes. When a recruiter calls you and says, "Hey Lenny, how much money do you expect to make?" and you say, "Oh, you know, 225. That sounds fair." You know, 5 years later, they call you and they expect you to make 225 again, not recognizing that you've grown exponentially since then. So, everything you communicate starts to serve as that value chain across the board.
Another mistake that people make, and you mentioned this a little earlier, it feels uncomfortable to get quote unquote confrontational or to feel like you're asking for too much. So, often will hide behind the easiest communication channel as possible. So, I might email you my demands, right? Or my negotiation. And the problem with that is I can't control tone. I can't control, especially when you're negotiating at high levels, if I push back, and the CEO that reads it's in the airport security line and pissed off and they read it, they might be like, "That bastard wants more money." That's all they take away. Even if you perfectly worded it, you got it all, you know, as clean as it can be. If you catch them at the wrong time, you have no control over how it's received.
Right? So, it's always better to have at least a video call, if not in person, so you can share tone, you can read body language, you can correct every step of the way.
Oftentimes we also try to negotiate through recruiters, right? You could do that, like, "I did the thing, Jacob. I talked to a recruiter. I spent a half an hour explaining it." The problem with that is you're playing a game of telephone. So, the same thing happens. I explain it to the recruiter. I get the tone right. The recruiter goes to the CEO and says, "That bastard wants more money." And that's all they communicate, right? So, people negotiate with the wrong folks. You have to go to the one who has skin in the game, who controls the P&L, who controls EBITDA. What's their motivation? That's who you want to talk to.
And so, some people might also have a concern with, well, how do I go around the recruiter? I don't want to look bad. We have to do that respectfully and now we need to plan what that communication looks like. And so the important thing here is just because it's uncomfortable doesn't mean you don't need to do it. It just means you don't know how to do it. So when something's uncomfortable, you have to run towards that because that's where the growth happens.
I love how tactical we're getting here. So following this thread, so the advice here is when you get an offer, and basically you're saying you should always negotiate in some way, you should push back. Your advice here is don't do it over email. Make sure you find a way to do a video call with essentially the hiring manager or the person that has skin in the game, like the finances and the budget.
There are situations, especially at high levels, more deals are closed on the golf course than they are in a boardroom. Right? So there are situations where you pull someone into a different element. This is called home field advantage. Right? So if you go to a company to have a conversation, you're out of your element in a situation where you may not perform your best.
The other thing people don't do is they don't control the time of which they have a conversation. CEO wants to hop on at 6:00 in the morning. Get your ass up, get that presentation and go. You need to say I'm not available at that time. And you read your own body language. I'm strongest between the hours of 10:00 a.m. and 1:00 p.m. I want a meeting in that time. So I will say I'm unavailable until that time becomes available. That also communicates scarcity, that you won't get pushed around. Right? So it's scary to do that, to say no to the CEO, I'm actually only available here. That also creates a rubber band effect that makes you more attractive.
Right? And so oftentimes, actually OpenAI did this, which is funny. And I didn't realize what the reason was, but I had some clients interviewing for C-suite roles at OpenAI. And so pushing Sam Altman around a little bit, which I'm okay with. I'm okay with that. But so they used to walk outside of the office and just walk downtown San Francisco instead. Right? You take someone out of the element, you get the endorphins going, you're walking and talking. The important piece here is instead of you and I being confrontational, like negotiating between each other, we're walking side by side. So it's almost like you could put your arm around the other person, you're solving the problem together.
These sound like minor things to consider, but the body language and the tone and the collaboration and the energy starts to flow more naturally when you do. This is all behavioral psychology, right?
Funny story, why I found out OpenAI did that was because they didn't want any executives going into the office because it was such a mess. It was like the biggest startup you've ever seen. So I used to joke that it was two midgets in a trench coat pretending to be a real company, right? And so anyway, the point was let's take them to a place where we can control and have an advantage over the conversation. So that's the way that you can think about where are you going to feel most comfortable? What hours of the day are you most comfortable? If you can bring someone to a lunch or a coffee where you're on even playing field or even your home field, you will perform better in those situations and you have more control over that than you may think.
So the advice there is try to get this conversation out of their office.
It can be, you know, but if I'm a product manager and I'm talking to a director, that may not be possible. Right. They might just say, "Look, you got to come into the office, you got to do this." Right? When I'm talking about a C-suite level, you could pull them out of the office, "Hey, let's go get drinks." Sometimes these deals are closed at 8:30 at night after a concert or something like that. So it's easing that situation. That being said, it doesn't mean you couldn't try. It's like, "Hey, I've got a couple of questions. Are you open to, you know, take a walk down AT&T Park and have a conversation about it?" You could pull them out of that, you can start to build a stronger relationship through that and you're more likely to get your way.
Talk us through the process you would recommend from: I get an offer, recruiter sends me, here's your offer, 300k salary, some kind of equity. What's kind of like the step-by-step? And I know this depends on the role, seniority, type of company, PE, VC-backed startup. Cuz it's very scary to push back and be like, oh, I want more. What's that first email / reply to that email look like typically? What are some phrases maybe you'd use? And then how do you open up a conversation where you plan to ask for more if you're meeting in person, especially cuz that feels so scary.
So first we want to approach with gratitude. Right? We're thankful that we want to move forward. Right? So, Lenny, I appreciate you making me an offer, right? I'm excited to work with you. We want to show enthusiasm, which also shows some confidence. We have to show that the deal is going to get done even if you're on the fence about it. Right? Now, it's not to say you're so excited that it's a sure thing, and you're not showing that you're disappointed even if you are.
Right? So, I'm grateful. I'm looking forward to working with you. I want to review this over the next couple of days. Right? Talk to my wife about it. You know, talk to an advisor so and so. Later on when you're a high-level executive, you're talking to legal, you're talking to advisors, you're talking to a coach. You may have five or six people see that. Right? Employment lawyer, all that. That stuff is expected. Right? So, you're going through the process. I'm going to take a couple days to process this. I'll get back to you. I may have a couple of questions. Right? But we'll loop back and it shouldn't be a problem. I imagine we start working together in a couple weeks.
Right? So, the point is you have to sell that the deal is going to be done. Which helps them feel like it's going to move forward regardless. Right? So, any ask that you make is not going to be egregious.
Now, oftentimes, the higher you anchor, the better you're going to perform. Which can be frustrating because you don't necessarily want to be like, "Oh, I increased it 40%," or anything like that. Now, this is where a lot of nuance comes in.
So, we might say, you know, come back 3 days later, want to have the conversation, let's take a walk in the park and talk through it, right? "You know, I've got to be honest with you, where this offer stands right now, I don't feel comfortable moving forward. It's a little lighter than I expected." Right? I may start saying something like that. And then just wait and see what they have to say. Maybe they say, "Well, what did you have in mind?" It's like, "Well, what's the chance you can share what the range looks like for this and what type of performance did you expect for each of these levels?" Right? Or they may say, "We comped you in the middle part of the range." Right? You might say, "What does the top end look like? You know, what must I do to fit those needs for you? Can you help me understand?"
Now, for a lot of folks, especially in this market, if we talk about what it was like in 2021 versus what it's like now, there's some over-leveling that's happened. So, there are people that are C-suite going back to VP and VPs going back to directors, especially as they go to bigger companies. Oftentimes I'll say, you know, "As we had this conversation, I'm likely a little more horsepower than you anticipated. Right? What's the chance we can come in and restructure the comp for the type of talent we're bringing in here?"
And so, this is a line that we used. There were three folks last year that were in ranges of 185 to 285, that deal landed at 1.1 million when we were done. With increases in stock, big cash increases. Two deals that were comped at 600 that landed at 1.1 and 1.2. So, doubled from that. And these were situations where the role started at senior director and were up-leveled to VP because they were reaching for top talent in that situation.
So, there are opportunities where it's easier to steer if you're really, really good. Right? I can see why some listeners are like, "Well, I'm not there in my career yet." In that case, this is just how it gets done. Right? This is how bigger moves happen. It doesn't mean you can't push for maybe 20% more naturally. That I would start with, "What's the chance there's a little bit more here? I was expecting this," right?
Again, more nuances, cuz if you open up what you're looking for too early in the conversation, that can be difficult to come back from later on. It's not entirely egregious, but one of the first things out of a recruiter's mouth is how much money do you want to make? Which is eerily similar to an illegal question, which is how much money do you make? Right? But if you say, "What do you want to make?" then it's okay. And that's where a lot of people get hung up as well.
I love that phrase you just shared of "What's the chance there's a bit more here? I was expecting number X." Is that the phrase you recommend, that approach of just a soft pushback just to see?
Sometimes. Again, it really depends on the leveling. If you are very senior, I typically don't want to re-anchor with a number because you should never be so sure of what you're worth that you wouldn't accept more.
Right? And when you anchor, that's the ceiling. And what often happens is naturally they want to split the difference. And so, there's a quick Hollywood story here.
So, we had a writer who had a $700,000 contract. Right? So, 700, and the agent that I was working with was saying, "This writer has the most aggressive attorneys in LA." Right? They're super aggressive. And I said, "Well, how do you know?" First of all, well, that's what they're perceived as.
So, the production studio offers this writer 700. The attorneys come back and say, "We want 1.3." Right? 1.3 million. And the studio said, "Fine, we'll do a million." And they settled at a million.
And I find that really interesting because the studio came up 300,000 and the attorneys lost 300,000. So, you split the difference right in the middle. So, if the attorneys said 1.5, would the deal have come in at 1.1? If the attorney said 1.7, would it have come in at 1.2? Right? How do we know? The way I see it is those attorneys weren't aggressive enough. We didn't find the ceiling there, did we?
That was lazy negotiating. Right? So, it still made the client 300,000. They were excited, right? The attorneys were excited. They made more on their commission. The agency was excited. They got 10% of that. But we didn't find the ceiling, did we? That was lazy negotiating.
Right? So, those are things that you got to slow down to really understand where is the value being made here. That movie could make 50 million dollars. You think a 1 million for writing was worth it? Or someone who controlled the creative there? I don't know. A 50 to one value exchange, why not push for more? Why not put some milestones in that, if this movie makes more than 50, my milestone is increased. This is how Tom Brady had his contract at Tampa Bay. Right? Win eight games, get a half a million dollars. Win 12 games, get a million five. Go to the playoffs, get an extra this. Win the division, get this. Get to the Super Bowl, X. Win Super Bowl MVP, get two and a half million more. So, performance-based triggers.
I love just how much you love this. It's just clear this is so interesting to you.
It's really nerdy, I know. I've obsessed over it in a weird way, but I don't know. It's been kind of baked into my psyche for a long time. Probably because I felt so powerless growing up that I'm so interested in how power works. And I was so scared to advocate for myself and I was the least assertive person that you know until I met my wife and she taught me how to be assertive, and now I'm off to the races. So, that's been helpful.
On that note, do these tactics work on kids and wives? Is this something that translates
Yeah, absolutely not. I would not recommend that. Especially if your wife
knows what you do for a living and hears you on the phone all the time and you try to say, "What's the chance?" And she's like, "No chance. Don't pull that on me. I know what you're doing," right? And toddlers are terrorists, so I haven't figured that one out. I've resorted to bribes, and maybe that is a little Machiavellian on the toddlers. You can be out of your mind working on that, but yeah, don't recommend it with your spouse.
I would pay a lot of money for a version of you for toddlers. Oh my god. I try to negotiate with my kid, I'm like, 3 minutes, he's like, six. I'm like, 4 minutes. No, six. He never budges.
5 minutes, he's like—
Eight. Although sometimes he does that, too.
Do you want a binky? And he goes, "Five binkies." And you go, "I don't know if we have five." And he's all, "10 binkies."
He's like, "Whatever you need, I'll get it if you go to sleep."
Yeah. Yeah, please sleep.
Yeah, we need this for toddlers. I would subscribe.
Miss Rachel's the closest thing we got.
Yeah. Okay, so coming back to this compensation number. So, you touched on this a bit and I think this is an important part of your advice: when the number question comes up, who should speak first? What should your approach be if they ask you this question of how much do you want to make?
Yeah, there's a decent amount of nuance in this, too. So, one thing you should realize is that especially earlier in your career, they're going to push on this harder. And that indicates that the person asking is really more looking for a commoditized or a price-sensitive hire, right? That can be okay. There's nothing wrong with sharing your number and getting a deal that moves the needle early in your career and even the middle of your career. That changes the higher up the ladder you go. And this is one of the reasons I want to share this: what got you here won't get you there.
Right? So, things start changing as you mature in your career. And so, when you're working with a top recruiter, they don't ask you about comp. They won't. The problem is top recruiters only reach out to you when you're very well known, and they don't reach out to you very often. So, it's very difficult to optimize for inbound attention the higher up you go unless you become very popular. Right? And then what happens is you share less information because people come to you in a different capacity.
Right? So, nine times out of 10, a recruiter reaching out to you is going to ask that number. One time out of 10, they're going to just focus on the value creation. Those are the ones you want to focus on, the best possible. But it could be confusing because so often you get a different side of the story, more of the commodity type stuff.
So, typically I'd recommend you answer, "I don't talk about compensation until we're ready to make an offer. It sounds like we're pretty far away there. I'd love the opportunity to learn more about the team, understand where the value comes in, and proceed down that path to make sure we're a good fit. Is that going to be a problem?" And then typically they'll say, "Yeah, it is going to be a problem. I just need to know a number."
Right? Now, I mean, it is very uncomfortable to do this back and forth and to say no. Especially Americans have a hard time saying no. I have noticed that other cultures can be more direct and just say, "No, I'm not going to do it." So be it. So, culturally there are a lot of differences in how this conversation happens.
And so, they say, "Look, we need a number from you." You might say, "Look, I'm uncomfortable doing that right now because I don't understand the scope of the role. Can you help me understand what you had in mind?"
Right? The reason I learned this is I used to be a marketing manager making $12 an hour in downtown San Francisco for Series A companies. Not knowing that $12 an hour wasn't a lot of money. I just didn't know any better. But then I looked at marketing managers and I saw that they made 60 grand a year, and I suddenly got offended at how little money I was making. Right? Then I got promoted to director in that period and was making $14 an hour. Good for me. And then I saw that marketing directors were making 110,000 at the time.
So when a recruiter called me, I pulled that. I didn't want to tell him I was making $14 an hour. They'd be like, who is this kid? He's not very good. That's a fake title. And instead I said, "What did you have in mind?" And they said, "Oh, we're looking at 110 to 130." And I'd say, "Oh, I'm on the upper end of that now." And so I went from $14 an hour to $120,000 a year in a single month, a single jump. Just like that. That changed my life. One negotiation. It's one of the reasons I'm so passionate about this. I hated the marketing work, for what it's worth. But I thought if I made a lot of money, it would make that pain of not liking my job go away. Turns out that was a fool's errand, but that's a story for another time.
Do things in your experience ever fall apart when you try to do that? Because that is a scary thing to push back on. Just like, no, I'm not going to tell you a number, and you're giving us advice on how to say it in a nice way. And then just like, what did you have in mind? The fear is like, okay, they're going to hate me and they're going to be like, oh, this is not worth it, we're going to move on. Has that ever happened? What are the odds that that might happen?
A couple things about power. Right? So, if you have the ability to say no, you have infinite power. The nuance changes when you don't have a job and you need to pay your mortgage; you might answer that differently because you want some. Right? Now, this isn't to shame somebody who's feeling that way. If you're out of work for 6 weeks in San Francisco, you're homeless. That's just the reality of the situation. So if I've got to say a number to get a job, that's fine. But understand that once you're employed and somebody's asking you and your needs are already getting met, why do you need to get pushed around?
Right? This is one reason that it's easier to find a job when you have a job. Now, I think this is a myth, for what it's worth, but this is easier because naturally your needs are getting met financially to a degree. So, naturally you negotiate more confidently.
When you're out of work and you have the discomfort of being out of work 6 months, 12 months, 18 months, you have an identity tied to a chief product officer role or VP of product. That's your identity in our country. We don't ask who you are and about your kids. We say, "What do you do for a living?" And when you are stripped of that title, it's uncomfortable. And we want that pain to end. And so, we give in to these demands because it's an authoritative figure and we want that pain to go away.
If we have the finances and the luxury of being able to say no, we increase our power. If we have the ability to push back and practice these difficult conversations, you will increase your power and you'll land at a higher rate because of it. So, can it get frustrating? Absolutely. But if somebody disrespects you through that process, doesn't that give you an indication of who the company's working with? Right? Now again, I might accept that because I need the money. I understand. But it's very telling how somebody's going to treat you depending on very simple pushbacks.
And one behavioral psychology hack here is we give someone a positive reputation that they want to uphold, whether they deserve it or not. So, in this instance, you'd say to the recruiter, "I want to thank you for being an advocate for me and for respecting that I won't share compensation figures right now. I appreciate that." And then they are trapped. They have to say, "No, I don't respect you. I have to do this." Or they have to say, "You're right. That makes sense. Let me move you forward," or not.
Right? Another option: you don't necessarily know if you're the best solution for that fit or not. And so we're obviously very ingrained: when a recruiter reaches out to you and they say, "Look, we're going to pay 120," and you make 150, you're like, "Oh, I'm not interested. That's not even close." I would recommend continuing that process anyway to see, as practice, what you can negotiate. You can always say no later. Just because having that practice is going to make you hundreds of thousands if not millions more in your career.
Alternatively, if you feel bad about, "Oh, I wasted their time because I was too much for what they needed," make recommendations for them. So when the offer comes in and they said it was a senior PM role, and what you realized is the JD and all of the work that you did is actually a director role, but they're not going to pay for a director role, right? How often does that happen? You get to say, "Look, this role isn't in alignment with where we're headed. Would you like me to make an introduction to somebody that's a better fit?" So you still get to help them. You remove yourself.
And then sometimes they say, "No, actually we do want the role to be more senior. We're going to extend for you." My first VP role came out of turning down a content manager position for 70,000. And 6 months later I landed a VP role for a quarter million. That was my first foray into VP. The initial offer was for content manager. So it came three, four levels up the food chain. That was a long negotiation, but these things can happen if you don't say no too quickly.
Along these lines, I want to touch on what feels like maybe the core approach you take, the core of your philosophy, which is to break out of this idea of some benchmark for a specific role and instead make it very clear to the company, "Here's the pain I will solve for you that is really important to you, and here's why it's worth paying you this much more, because it's such a big problem for you." Talk about just that mindset.
So, this really comes down to having curiosity and showing curiosity about the actual problem. Because usually if I'm speaking to a room of 400 people, which I'll occasionally do with some communities, I'll ask them, "Who is actually doing the job that's on their job description?" Nobody will raise their hand. It's not like you have your job description right there and that's what you do, right? There's always so much more that's not documented.
Right? Now, when you're going into a position, you see a JD and you're like, "Yeah, I could do all those things." But there's so much more, right? This is another reason that anchoring to a number too early is tough. Because you anchor to, "Oh, this is fair for a senior PM role." Then you go through the process of interviewing, and it's very clear that it's a director role. You're going to lead five people. They scoop another team under you. Oh, we're going to put a product-led growth motion under you, too. There's a whole engineering pod and there's this and there's this. All of a sudden, that's called scope creep, right?
So, they scope creep the role. They talk about how they want a senior hire. They're excited about you. They get you excited about it. And then they give you the offer and it's actually 20% under the number that you originally shared. And then you say, "Okay, well, this looks like a director role. I want X." And they say, "But you said you only wanted 140." Now they're using a number against you, and it's very awkward to come back from that. And so, that's why we don't want to anchor too early. We want to understand.
And so, this is one thing I wish, especially product engineers, designers, that side of the product stack, I would love for you to treat more of these like a sales conversation. Right? You are an enterprise solution, a consulting solution that is several hundred thousand dollars if not millions of dollars a year. If you were to sell that product into an organization, think enterprise B2B deals, and I know I'm getting a little buzzwordy here. Think: take an enterprise B2B deal to Salesforce and you're going to sell a million-and-a-half-dollar product. It would take you 18 months to develop the relationships and close that deal.
You have to develop champions in the organization. You have to understand what value you can create for each of those people so that they can advocate for you. You don't come in and pitch them the price right off the bat. You need to understand the value. So, through the process, it's a discovery process. Why am I here? What gets you excited about me? Right? That's how we start a conversation.
Too many interviews start with, you know, tell me about yourself. Tell me about the stuff in the past. If you're talking about your past, you're on the back foot and you're losing that conversation. You're the one revealing information. You're not getting anything. We instead want to have a conversation and say, "Look, some of the best interviews I've always had felt a little bit more like consultations or brainstorming sessions. Are you open to having a chat like that today?" That's the first step. Typically, they say, "Yeah, that sounds way better than me trying to drill you with questions."
So, let me ask you, what are some of the things that you're excited about? I imagine, Lenny, you're excited to talk to me because I can help some of your audience negotiate. You've seen proof where dozens of your subscribers have made more money with the article we wrote together. You've even seen that some of your guests, unknowingly, have been negotiated against with some of the work that I've done. Is there anything that I missed? What's exciting to you? So, I want to clarify why I'm in the room with you.
Right? So, we do that as a PM. Now, we move to labeling. It sounds like you have a challenge with this product line. It sounds like we need to move or ship product faster. It sounds like AI's been a problem and we need to shift towards native AI. Is there anything that I missed? Right? Then they're revealing information. You take control of that conversation.
And then we want to ask, "What have you done about it? How big of a problem is this in the organization?" This is basically a SWOT analysis. What are some of the things you've done well? What are some of the areas where the team failed? What are some of the things we should be doing that we're not? And what are some of the things we absolutely shouldn't touch? So I want to ask all these discovery questions. They're like, "Oh, look, it's a $10 million problem," or "We've gone through five different PMs in 6 months." And you're starting to understand where the dirty laundry in the company is.
Then we get to sell the vacation. Right? Then we get to say, "Look, all right, so fast forward 6 months from now and we're working on this problem together, and we've solved the churn in the engineering department or in the design department or whatever. We've solved that and we've got two product launches under our belt. When you head into that next board meeting, how can we ensure that your head is held high?"
So what I'm doing is I'm psychologically walking them to a position of, like, a painless position. I've removed the friction and the pain from their shoulders and I've forced them to visualize a utopian situation, and who is right next to them doing that? I was. So when it comes to your competition, there is no competition. I'm the only person who walked you into a vacation that you want to be in, looking forward to your head held high in a board meeting that's usually stressful, but this time, because you worked with me, it's not stressful.
Then all of a sudden, when it comes to the offer stage, there may be five other PMs, but I can only imagine working with Jacob. And so when I push back, the likelihood that they break the rules is significantly higher than if I hadn't done that.
This is amazing. So trying to just summarize what you're sharing here, and I think it's important for people to also know you can do it in your own words. This is likely not something
you'll just be able to pop out and do, like, this is something that takes time to do well and it feels awkward probably, and that's why people work with you, that they probably role-play and all these things. But still, there's things people can pull out of this that they can do on their own.
It could be tricky to understand where your value is, right? Cuz you're so close to it. You just do this every day. And for, you know, product folks that only listen to product folks and are in the product ecosystem in your bubble, Lenny, they're not seeing the impact on marketing. They're not having those conversations necessarily. So it's so ingrained in everything that you do that you could functionally be excellent, but in order to break these boundaries, you have to be cross-functionally understanding how it impacts others and the motivations of others. That's when things really start to unlock. And that's where just understanding a little perspective can be helpful in that outside influence there.
I think this is important to just briefly summarize your approach. So the idea here is figure out in many ways what matters most to them, what problems do they have, what they see in you, just understand the landscape of where you could bring tons of value, help them see that here's the problem that I can help you with, here's the problem that you have that we need, here's the many problems that we can help you with. And then help them visualize, you describe it as sell the vacation, help them visualize, okay, now that this is solved, how awesome would that be? And there's all this psychological stuff you're throwing in there. Just, how do you actually do this?
Really make this concrete with a quick story.
Do it.
So, there's a very famous musician who was born the same year as me, for those super sleuths out there, who had a tour, a billion-dollar tour, and a documentary. And the director of said tour was a hot commodity in Hollywood. Every agency wanted to sign this director. This director didn't want to just do movie documentaries, right? Wanted to start producing actual movies. That's the dream, right? So, every agency wanted to sign this hot director who just did this billion-dollar deal with... People already know who it is, right?
And so, my client, the agent, asked me, like, we got to sign this. It would be stupid to go to any other agency, right? We've done this, we've done that, we've represented Julia Roberts and Matt Damon and all these things. He's just name-dropping, right?
Now, this is actually a problem, because if we're leaning on logic and credibility, we're losing. All right, we need to sell the future and own the emotion. And so, she just asked me, how do we close this deal?
And to me, this was very simple. I said, if you already had the job, who would you introduce him to? If you already had it, the deal's already signed. So, put yourself in the position that you're already doing the job. That's why in the interview process, if you treat it like you're consulting, you're doing a value exchange and you're increasing your value and you're asking the right questions. If you feel like you're on the outside and you're having to say, well, look, Lenny, I did this and I did that. Did you see I have, you know, 3 million words written? Why wouldn't you want to be the guest? I don't care about what you've done, I care about what you'll provide my audience, right? So, in this deal, we get into the meeting, it's a big day, right? And I said, schedule the appointment already. Work with the assistant, schedule the appointment, right? With whoever it needs to be. Needs to be a big-name person.
So, we go into that interview and inevitably, the conversation goes, why should I sign your agency? And so, my client says, what are you doing on Friday? I cleared a lunch with your assistant. And he says, well, I guess I'm going to lunch. And she's like, great, I'll have you meet Steven. And he said, Steven who? And she said, Steven Spielberg.
And then, some form after that, it was, where do I sign? Because the meeting was already set with Steven Spielberg. For somebody who wants to get into film production, what better meeting to have? Right? So, for the other agencies, they're like, "We're the greatest thing. We've represented this director that did this media tour, and we did that." They lost because we sold a vacation and we made it a reality right then and there. And the value was clear.
So, there's both this mindset shift of, I'm going to try to actually help you figure out where I can be helpful and where the problems are, and then start actually thinking about how to fix this. And also, there's try to even do it. Sounds like you could just do it.
Can do it. So, one of the tricks of my business is I can plant seeds with my clients really easily because I'm on the phone with somebody and I'm understanding who they need to connect with. And so, they might say, "Oh, I've been interested in getting to Google or whatever." Let's say they're in product. I say, "Oh, I have somebody in product at Google. Let me make a text for you real quick." And I'll just do it while I'm on the phone. Just hold on a second. Hold on. And then what happens is they get the beep. That's reciprocity. I'm triggering a reciprocity imbalance. And then I'm making another one for them. So, I'll sometimes do two or three introductions right then and there, and they see the value before I'm even off the phone.
What I've also done is I've given three different touch points where I can make sure that that person is following through. I can get a 360° view of that person. I can ask one of those people to prompt them to close with me if I need to sell a deal. I'm getting a reciprocity imbalance. So, what I want to do is show that I have the resources to support them, whether they sign a contract or not.
And that's where we go. In this instance, if you want to role-play with me for a second, something that would be really exciting. Lenny, I want to understand what's exciting to you. If today's podcast was the best podcast, the highest performing podcast that had ever happened, right? What would that mean to you? And also, what did we do to make it so successful? What are the comments that people had to put down below? What are the things they said to make you feel like my conversation with Jacob was the best conversation I had all year? What would that look like to you?
I immediately love this question. You know, it sounds to people like this is manipulative, and it could come across as that as an external observer, but to me I'm like, this is exactly what I want to achieve, and I love that you're thinking about this, that I want you to be focused on this, and I would do a lot to help make this happen. I guess to answer your question, I would just love it to be very concrete tactical advice that people can use to help negotiate their comp. And they spread this with all their friends, that are like, this is the best thing you've ever heard around comp.
And one of the things that we can do is that we plant what you want someone to say in that conversation as well. So when I'm talking to these executives and I'm making the introductions, or introductions come to me, sometimes I'll ask, I'll be curious, like, when you go back and you share with a friend, what are you going to say about me? Are you going to say Jacob was really helpful? Or are you going to say that Jacob was an... Right? I'm curious. And sometimes I just make a complete reframe so there's no other option. Right? Well, I'm obviously not going to say you're an..., so I'm going to say you're the great thing that I want you to say. I'm controlling the narrative I want them to perpetuate.
So in this instance, and maybe some of your readers are going, this guy's a total manipulative jerk, right? I will say I hope that you use this for good and not evil, but this is just the way power works, right?
I would hope that in the comment section you say, Lenny, this was such a refreshing and energetic podcast. This is what we want more of. This is exciting. We've done a lot of stuff in AI, this was very cool and different, right? So I'm suggesting, if you felt that way, share something like that below, right? Too many YouTube videos are like, oh, like and subscribe, and that's all they do, right? Which does trigger action. It's a very simple thing. But when it comes to navigating your net worth and negotiating for power, these executives at the top control what every other person is saying.
Naturally, they know when somebody's talking about them when they're not in the room, and they not only know about it, but they know what they said about them. Similar to when somebody's like, "Oh, Lenny, we're going to do reference checks on you." What's the first thing you do? You call all those references and you say, "What are you going to say about me?" Right? Ideally, you can control that to some capacity and improve the likelihood of you moving forward. So, we already do this. We just have to integrate it into some everyday conversations and you could better control outcomes.
It's the same interview process. When you go back to your committee, are you going to say, "Jacob solved XYZ and we're excited. Slam dunk. Let's move forward." And I like really quick, like, "Slam dunk." Right? Easy to remember. Or are you going to say there's a couple gaps here, and some of the competitors that we have, or some of the competition, seems more fulfilling?
And I want to ask for that feedback while I'm still on the call with you. I don't want to wait for an email to say, "I'm sorry, you're not a fit." And then you ask for feedback and you don't get any. I have to do it while we're live in person, because you can't deny me in that moment without it being awkward. So, what are you going to say? Is this a slam dunk? What's one thing I should have asked that I didn't? What are some areas that the other candidates excelled that you wish I showed more of? I want to understand where those gaps are so I have an opportunity to address them. And then, if I didn't make the mark, I'd say, "I'd love to have a conversation with you next Thursday to talk through that in more detail. Thank you for bringing that to my attention." And you close the next conversation. You don't give up, necessarily.
You know, that was another monologue, but that was a little bit inside the mind of how I think about these things.
No, this is so awesome. So, you know, if you think about a hiring manager having someone... Let's imagine I'm interviewing for a role. If I come to them and say, "Here's the problem. I'm going to solve churn for you. I'm going to fix your onboarding flow. I'm going to figure out how to level up your design experience, cuz I know that these are big challenges for you right now." If I was the hiring manager, I'd be like, "Holy..., this is awesome. I just need someone to come in and solve these problems for me. This is...
And you better deliver. Right? And that's the other thing. It sounds like if this guy can't deliver, it's not going to happen. If this gal can't deliver, that's frustrating. Right? I'm not suggesting go so far outside of your comfort zone that you feel like you can't do it. Right? Because that reputation will haunt you. Right? You have to really understand.
And I would also add that I wouldn't be so sure that I'm going to fix the onboarding flow. I wouldn't be so sure, I'm not so sure that you know that's the problem yet.
The longer we can drag out the hiring process... And this sounds like pulling teeth, especially when you're unemployed. Like, I just want the pain to be over. I'm asking you to slow it down. The more you slow down the process, the more you fight back about the manufactured urgency of us needing to get into that role sooner, the more information you're going to understand about that company and how you could really help.
Right? So, you could say, you know, Lenny, I hear that you want to fix the onboarding flow. I hear that. I hear this. But it sounds like that product might be deprecated anyway in this wave of AI. Is that a possibility? What I don't want to do is prioritize something that the team's going to cut. Right? That's going to hurt the P&L, or whatever. Now, I can only ask that question if I truly ask the right questions to understand.
Right? So, you may come in... This is the same concept as never be so sure of your worth that you wouldn't accept more. You're so sure of the job description, that they need these three things, that you don't even try to ask the questions to understand what the deeper problem is. And this is going back also to why founders might be frustrated with my talk track. I'm not asking for you to take your pie and give them a bigger slice. I'm asking for you to work with somebody to expand the pie so everybody gets bigger slices. That's the plan. And if you train your candidates and you're more revealing, and if their performance is tied to it, naturally they need to ask more questions to understand how to make it true. That's what we want. That's keeping companies up and to the right.
I like that you went there around don't over promise, because it's easy to say we're going to solve all your pain for you. I'm going to be the best in the world.
...promise. You under promise, over deliver. Always. Under promise, over deliver.
This episode is brought to you by Omni. Many product teams today are in the process of debating how to ship AI analytics. The hard part is obvious. Having an LLM guess at SQL in production is a huge mess and just a bad idea. Omni takes a different approach. They have a semantic layer built in so that when you embed their analytics, the AI actually knows your business definitions, not just your raw tables. You can test queries, validate the reasoning, and lock down permissions before anything hits production. If you want AI analytics in your product without building the whole stack from scratch, check out omni.co/lenny for a free 3-week trial. Companies like Perplexity, dbt, and BuzzFeed use Omni to ship analytics their customers can trust. That's omni.co/lenny.
There's this balance of being confident in your abilities to achieve something big and solve problems, and then there's this other piece of just don't over promise. Is there anything you help people do to help feel more confident that they will actually be a huge asset to this company and they're worth all this extra money? Is it like a pep talk? How do you help people?
Yeah, part of my hat is the hype man hat, right? You got to be a man to a degree, and I work with some of the most privileged and successful people in the world. Right? It's not that hard to say, "Look at your life, and look at your choices. Most of the things you've done have been good." Right? At least financially. Right? We could debate about the ethics of the companies they work for and those things. Right? Now, most of the decisions that you've made in your career have made you a top tenth of a percentile of the earners on the planet. Don't tell me you're not confident.
If you can't hold that... Another thing that I do is that I reframe everything in a language they understand. So, if I'm working with a sales leader, the job search process is an enterprise sales process. If you understand enterprise sales, you understand how to do this. You just don't know how to do it for yourself. If you're in marketing, you should know about positioning and market research. That's the same thing as going into a job market and understanding what to do. You understand that an inbound lead is much easier to close than an outbound lead. If you're in product and you're orchestrating a PRD, right? It's the same thing. You're understanding the users' demands. You're creating for those demands. You're developing the right flow. You're making the design as simple as possible. You're eliminating friction. That's a term I use a lot, which I know product leaders will use also. We want
to eliminate friction. Right? How does that look in your job search? Well, what does the customer want? Who's your buyer? The buyer is the hiring manager. Maybe it's the chief product officer. Maybe it's the CEO. What do they care about?
When you're doing it for a company, you know which customers to interview. You know how to do that. Well, you need to interview lots of CEOs. You need to interview lots of salespeople who are trying to solve this growth problem or lots of AI side. And again, it's not just product. Right? So, you're now interviewing your customers. You're understanding their needs. Now, you're designing solutions for their needs. Now, how do you make it as frictionless as possible so it's a no-brainer and they go through your user flow as easy as possible?
So, for product folks, instead of thinking, "Wow, this stuff sounds like Machiavellian manipulation and it sounds like a power trip and it sounds like something I could never do because I'm not... Maybe I'm not as gregarious and maybe I'm not a 6'3" tall white dude in California who's got that sales persona and he's got that extraversion. I'm not that." Don't be me. Don't be Jacob Lite. Be you, your authentic you, and apply it to what you already know. You know how to do this in product. Design it for your career.
And you remember the early days of writing PRDs and how rough it was? Remember how rough it was to go back to the engineering team and just little by little get product sprints out where the product is just moving a little bit at a time. Remember how hard that was? The early days of managing your career like this will feel like that, too. But you also know that if you're 10 years in your career, this stuff becomes second nature. Right? So, I want to reframe to the experiences that you already know and that will develop confidence.
I like this framing you're referencing here for product people of this idea like you're basically trying to position yourself the way you'd position a product, kind of the value prop of the... basically as a product team, you're trying to sell people on here's why this product is worth paying money for. And you do that by understanding, you do your research, you understand their pain points, you understand how to position it so that you make it clear this will solve your pain point. Essentially, that's what you're describing from when you're interviewing is think about it that same way.
The part I don't want to gloss over is making it frictionless. Right? So, interviewing is a skill on both sides. Most people don't know how to interview very well. It's tell me about yourself. Like, tell me about this product you built. Tell me about that, how that looked. You don't get anywhere talking about the past. Like you might build credibility and all that, great. You don't start solving problems in that process. So, they're like, "Okay, well, I saw that." Now, you're going to go on to the next person. They're going to do the same crap. Right? Same thing, same thing, same thing. So, you repeat your story ad nauseam and you never learn anything and you never grow.
So, how do we make this frictionless? Well, I want to make it cognitively easier for you to have a conversation with me by leading. That's why I had that framework I was talking about earlier. Like, why am I here? What are the problems you have? I suspect it's this. What have you done about it? What would it look like if we solved it? Now, I'm taking so much of the pressure off of you. I'm controlling the narrative and I'm collecting more information while revealing none about my comp expectations. And what I'm focused on is creating as much value as possible.
Now, there are situations where companies don't have the budget, right? Like, this isn't a miracle drug kind of thing. But I'm making it frictionless to at least get to the part where they want you. That's the first step. They have to want you for you to have any leverage.
Right? Then even in the interview processes, I might say, "Hey Lenny, you know, I suspect the next person I talk to from your ecosystem is Marc Andreessen. Right? Can you give me some advice on how I should work with Marc? I want you to coach me on how to deal with Marc." That's going to make it more frictionless, right? Now, I also want to put you in a position to be a coach because coaches want their players to succeed. So, if I'm having you coach me, psychologically, you're going to go talk to Marc and you're going to say, "Hey Marc, you're going to have to talk to Jacob for all these reasons, right?" Then when I talk to Marc, I get to say, "You know, Lenny shared that I should talk about X Y Z thing. Is that really what you care about?"
I'm making it frictionless across the process and I'm closing the next part of the conversation regardless of whether you wanted me to introduce me to those other people or not.
So, you might say, let's say you're interviewing for a product role, I suspect you want me to talk to the head of engineering. I suspect you want me to talk to Clay, the VP of marketing. And I suspect you want me to talk to Catherine, the VP of sales. Right? What would you like me to say to them? What's the message you want me to share? And they may not have had them in the interview process in the cycle, but I'm putting them in the cycle. Like I'm making it easier for you to know who to introduce me to next. And then I'll even go as far as saying, "I'm not available again until Thursday. What's the chance that time works?" So, I'm building scarcity about my time. I can meet with this VP then, but I'm making myself stickier in the organization. I'm getting more knowledge about what people need.
Right? So, this is similar to selling an enterprise deal. You're building champions in the organization that love you, and they're all coaching you on how to work with each other. So, you're getting the inside scoop on how to navigate that. That's how you become hyper valuable. You need to create that leverage if you want to take that standard 20% we talked about and make it 40 or more.
That's why it starts much sooner. Because if you're not doing that, if you come to me and you're like, "Jacob, I have an offer." I can get you maybe 40. Right? If you come to me sooner, I might have elevated that initial offer 40 without you knowing it, and then we moved it even further. Right? So, it's a big process that we need to be mindful of.
So, it seems like a big part of your process and advice is to flip the interview as much as you can to extract information so that you can build a case of how you will solve their pain. Say you're like an IC product manager interviewing at Meta. What are the odds you can kind of flip these conversations or take a big chunk of that talk from them asking you, you know, their standard questions to you asking them what are the biggest problems, what would be awesome if I came in, like all that stuff you shared about, to extract to build this case later?
One of the things I found frustrating about IC roles is they're not often rewarded as well as leadership roles, which is frustrating because there are a lot of very talented ICs. Now, I have seen specifically with Meta, I actually interviewed for a Meta IC manager role like an i9, it was like 1.2 million a year. They were specifically hiring former CEOs and I found that to be interesting. They hired 150 growth PMs at this i9 level and they were rewarding them very well.
I don't think it changes. I think that whether you're a leader of people or you're a leader of process, you're still a leader. And the reason I propose taking ownership of the conversation isn't to be steamrolling or talking over people, like I'm not saying do this devoid of context. You don't just blow out and talk over somebody and ramble, right? Which I'm one to talk, apparently. But you go into this conversation and you even flow with them. Right? The reason I want you to take ownership is 'cause I can't control who you're going to get on the other side of the line. I can't control the mood they're in. I can't control their motivations. So, as a coach, I can't control how they show up, but you can control how you show up.
And we can work to navigate and then you start to get some, I guess, nuanced skills where you read body language and you feel comfortable saying, "You know, Lenny, I saw that that maybe wasn't the right thing to say. Can you tell me more about that?" Then you start getting confidence, and I say assertiveness, not aggressiveness. There's a difference. And so, that comes across as confidence.
And so, I don't think there's a difference between being an IC and being a leader in terms of how you approach this. But I have noticed a difference in the pay and that can be frustrating. So, that means that if I were working with more IC folks, I would ask questions like, "It sounds like, you know, independent contributor roles are very valuable at Meta. Can you share a little bit about how they're valued compared to leaders on the team?" I might ask a question like that. Because again, they can't say we value you less. I've given them a reputation where they have to say we value you.
Then you get your offer, you check Levels or you check some of these benchmarks because we all do, right? We look, we want to know, right? Maybe we call up a couple friends that are a similar level. Then you can use objective criteria against them. You're like, "You know, you mentioned that you valued ICs as much as leaders. Right? And I just got curious, so I did a little digging and it looks like this is about 30% under what a leader would make. Is that normal? Right? I appreciate you being an advocate for me and I'm pushing back. Can you help me understand if we can lift this to be more equitable?" Right? I'm using information I gathered for them and I'm not just beating them up with it. I'm just saying like, you said we treat this fairly. Prove it. Or prove to me that you lied.
And this works, is what you're saying? 'Cause like if I was the hiring manager, I'd be like, "No, I'm sorry, that's just not how it is."
I mean, in many cases it can be, right? But I'm trying to open up an emotional conversation more so than logic and credibility, 'cause you lose. You will always lose the logical and credible argument against a company. There's information asymmetry here. Meta negotiates thousands of times a day. You negotiate four or five times in your career. That's it. Right? Thousands of times a day. Recruiters, thousands of times a day. You are at such a disadvantage. This should also give you confidence to negotiate in the first place. You are at such a disadvantage.
Right? I just wrote an article on the game of Werewolf as an example about how important information is. So, the game of Werewolf is pretty simple. Say there's 12 people sitting in a room. Two, three of them are werewolves, right? They draw a card at random. Three people, two people, whatever. They get their card and they know they're werewolves. There's a day and night scene and the werewolves get to reveal themselves to each other. So, they say, "Oh, you're a werewolf?" "Yeah, okay. We're werewolves." Right? Then they go round by round and they politic to vote somebody off of the table. Right? Only two, three people understand, right? When the werewolves reach parity with the villagers, the werewolves win.
Right? In even a six to one or a five to one situation, werewolves win 60, 70% of the time. It shows the power of information. They understand everyone else is clueless. They know who's dangerous, they know who's not. And that's just an outnumbered situation. Now, these companies have significant leverage over you. They know what people make, they know what others make, they know what they'll accept, they know their budgets, they know how to change their budgets.
And what I find interesting, especially with executives, they push back on this process. And I'm not going to lie, it's much easier for executives to do this than it is for middle managers or lower. So, if you are hiring manager Lenny and you put your director head on, like it's easy to deny somebody like that because it's a little bit easier to find another product manager. A little bit, right? If we do our job to differentiate, then we're doing better there. But, executives that are afraid to push back, like your job is to make these rules. You know who to influence to change them. You understand how the P&L works. That's what you do for a living. And you're telling me there's no flexibility? You built it. Humans built this. This is not concrete authority. This can be influenced. Why not try?
Let's try to summarize maybe the top five tactical tips that you've shared. If we're just to kind of go through in bullet points, just things people should keep in mind when they're trying to negotiate. Like one that comes to mind is don't show the number first. Try to get them to share the number first. Is that right?
Yeah, you also have to know how to respond if they share the number first. I'd rather no numbers be discussed if you're open to just waiting it out and saying, "So."
Important pieces. So, the first one is you never be so sure of your worth that you wouldn't accept more. I think Chris Voss quotes that quite frequently. The other one is never split the difference, and I have a good story about that. So, just because somebody says, you know, you started at 100, you say 200, they come in at 150, that's lazy, right?
One brief example of this, I had a chief revenue officer and they were paid $350,000 base salary, 350,000 bonus. So, 700,000 cash potential each year. So, that's called on-target earnings. They'll make 700. When we negotiated their severance, we said we wanted 6 months on-target earnings. It was all agreed, right? The paperwork comes back and it says 6 months base salary, not on-target earnings. So, that means 6 months of base salary is like 187.5, right? So, they cut his severance in half by doing that. Now, his response was, "I'll just tell the CEO, like, let's up that 90 and it'll be down 90." He was going to split the difference, like 260 or something, whatever the math works out to. And I said instead, simply ask, was that a mistake? Right? "You know, we had discussed on-target earnings, that was intentional. Was that a mistake?" He said, "Oh, yeah, must have been. Let me just tell the attorneys to fix it. Feel free to redline it."
So, he almost lost 90 grand just splitting the difference, if not more, right? And then turns out 12 months later he got fired and then he was able to recoup $350,000 over 6 months. So, little things like trying to split the difference too early can be painful. So, that was two points, I think. You know, this is the part I'm bad at. Trying to get a list of five.
This is great.
Patience is more important. Like things need to slow down. Haste equals risk. The slower you go, the more opportunity you have to collect information so that you can build a compelling case, right? That's important.
I am a big believer in Aristotle and his principles of rhetoric and ethos, pathos, logos. And so I've mentioned a little bit of this in their more common tone of logic, credibility, and emotion. Timing is another one that we don't often talk about. Kairos is important. But too many executives lean on credibility and logic because we're trying to do that. We don't show emotion. We don't show the authentic side of ourselves in corporate. I think oftentimes 'cause we're working soulless jobs that we don't believe in and we're just trying to make do and survive for our families. I think there's a greater need there.
The emotional side is where a lot of deals get unfair. So if we understand how to tap into that, I want to say Chris Voss, I keep mentioning Chris Voss, but I think he calls it tactical empathy, right? Which sounds more Machiavellian than anything I've ever said, right? But understanding those motivations and understanding how to play on that can be important. Right? So when we talk about giving people a positive reputation, we're playing into some emotions here. So if I'm a female negotiating with another female, I might say, "You know,
I appreciate that you've always been an advocate for women and you support one another. Like that's something I respect about you." Right? And then their comp comes in lower than a man's comp, you can call them out on that and say, "If you were in my shoes, what would you do?"
That's one of my favorite lines. If you were in my shoes, like go backwards 5 years in your career, that's where I'm at right now. If you were in my shoes, what would you ask for? I love that when negotiations stall also, right? Like you know what's possible here. You know what levers we have. It sounds like we're capped out here. If you were in my shoes, what else would you explore? And you start to go that route as well.
The other piece is this is a collaboration, not a confrontation. So if I could give visual advice, oftentimes... Oh wait, it also could be difficult in a Zoom. Like you and I are kind of face-to-face. Like we have this problem between us, right? That's an adversarial position. I want you to physically pretend that you're in the same room and I walk to your office and I put my arm around you, if you're comfortable with it, and instead of us arguing over something, we're whiteboarding a solution together. I want collaboration and that's how we break down walls and barriers because you're sharing information, I'm sharing information, those types of things.
I think that was four, maybe it was five. Another one is make it about we, not about me. Right? So, another severance conversation with a chief marketing officer. This is a hundred to two hundred million-dollar private company a couple years ago. So, she comes in, she gets offered $340,000 base salary, 30% bonus, equity, right? We tried to push on all that and the CEO said, "Look, one of the things I pride myself in is that everyone here has $340,000 base, 30%, and the same equity package. Everyone on the executive leadership."
Right? Now, she was getting pulled from a hot company, which is risky cuz she was safe there. She actually was getting a raise coming to this company. So, we didn't need to push on more money. What we went for was severance protections. Right? And so, we asked, like, standard is about six months, maybe plus another month for every year served. And the CEO is like, "Oh, we've never done that before." And so, instead of it being like you're negotiating the terms of your divorce before you get married, that's what's awkward here, we said, "Well, given that we've had a problem with talent being poached, you going elsewhere, and we just did a big RIF, wouldn't it make us look good to proactively give everyone on the executive leadership team six months to show that they're safe and committed to the company?"
And then we fed that idea to the CEO so the CEO could look like the hero. More importantly, when my client came into that company, she looked like a hero because everyone's like, "That's the woman that negotiated us all severance protections." Right? So we used the company's equitable policies to do that.
Now I will say that's not common. Right? So the folks are like, "Ben, that's fantastical." That may not happen. Like especially with private equity, it usually doesn't. Right? There are ways that we want to appeal to humanity more so if we can.
Bonus point. I know I'm monologuing a lot. Don't be afraid to get creative. Like creativity is interesting and one time we got someone a G-Wagon after being like maxed out on comp. I like this story cuz it's so out of this world. You're not going to get a G-Wagon. I promise you it is likely not going to happen. But we had the CEO who had two offers that were both 2.4 million and they were stalled. I know, first world problem, right? Like tiny violin. 2.4 million a year, this CEO deal. And she told me, and this was just a joke, like this wasn't some Machiavellian plan, she was like, "Look, I don't know which to choose. They're both maxed out." And I was trying to say which one would you like more. She wasn't giving me anything. Right? They're both fine, whatever.
And I said, "Well, I don't know. What kind of car do you like?" Right? And she's like, "Oh, I love Mercedes." Right? And I was like, "Tell them that." But jokingly, cuz they inevitably came to, "Look, what's it going to take to hire you?" And she's like, "I don't know. Like, oh, maybe a company car." And they said, "Well, what kind do you like?" And then she said, "Mercedes." And they're like, "Done. What model?" And then she's like, "Oh, G-Wagon." And what happened was all the budgets were capped. But it was a company write-off to have a 6,000 lb vehicle. So there was a $350,000 car added to her contract that was a company write-off that reduced the tax expense. So, like that's not going to happen. I don't suggest people go ask for G-Wagons, but the fact is we came to a stall point and we found a solution for that.
I love these stories. Another tip to share just that I want to double down on is don't negotiate over an email. Make it in person if possible or video call, right?
Yeah, absolutely. You have to be more comfortable understanding the body language and the tone. You're picking up these things that you can't control when somebody opens their phone. Like the worst thing is they're on their way to pick up their kids at school and they open your email and it just doesn't sit right with them and they're in traffic. Like you can't control whether someone's going to do that. Or like I said earlier, being busy at the airport, rushed through security. Or they just got off a call with somebody that's frustrated. But if I hop into a video call and I can see that you're visibly frustrated, like if for whatever reason you look like your toddler kept you up all night, I'd say, "Hey Lenny, would you like to reschedule to a time that feels more comfortable for you?" Right? So that we can get the most out of our time together. Like that is a blessing, right? You couldn't do that over email.
Say things actually do fall apart. Say they just pushed you hard and they're just like, "Mm, okay. We're going to move on with another candidate." Or they make you an offer and they rescind it, or they promise something and they don't deliver. How do you approach when things go sideways?
Couple elements to that story. One, the not delivering piece is more common. Rescinded offers, I have never had a client with a rescinded offer. What I will get is a no. This is the top, take it or leave it. Right? Fine. They get an ultimatum. Fine. I have, however, helped somebody. They weren't a client. See also a CMO. And she was offered an $800,000 contract total cash-wise and it was rescinded. And so I took this case on pro bono. I got a phone call. I was like, I just want to see how this plays out, right?
And she was in tears. She lost this deal. Turns out she had a career coach who said, "You need to negotiate like a white man." Like that was her advice. Like you need to be aggressive, you need to do this, you need to do that. Like you need to negotiate for your worth, which, you know, I understand the appeal of that, like I would understand a woman that wants to negotiate like a man and get hers, I respect that, right?
In this situation, the context that was missing is that she was negotiating with other women. So she was negotiating with this female CEO and the three other females on the executive leadership team and they rescinded the offer because it sounded like she was a bad cultural fit. Because she was acting like a man. Like she wasn't being her authentic self. She was acting in this persona that she wasn't comfortable with. And to be honest, she said to me, "I wasn't comfortable with that advice, but I did it anyway because women should stand up for each other. We should push, right?" And I commended her for that.
And so what we did was I said, "Look, call the CEO, explain what happened. Share that, you know, obviously it's important that women take care of each other, right? And it's clear to me that you have. There's that positive reputation, right? I got to be honest with you. I hired a coach to try to understand what to do because in the past I failed. In the past I haven't been my best advocate. In the past I've done less. I suspect you know what that's like."
Boom, shared identity, right? All women know this together collectively. This is a shared identity tribe thing, right? "I made a mistake and I disagreed with the advice, but I did it anyway cuz I had to." And they brought the offer back on the table for her authenticity and transparency. So, that was the path. It was two phone calls to come up with that idea. She got that deal back on the table, is now happily making 800,000 a year.
Right? So, when things go south, approach it with honesty, integrity. Say like, I made a mistake. Take ownership. Extreme ownership really helps here. That could probably be one of those points. When you fail to deliver, take ownership of that. Take that note. It may mean you're getting level set a little bit in your career. That's okay. You're still growing.
I love that approach of just like, okay, I hired this coach, they gave me bad advice. It was actually...
Feel good, too. I was like, shoot, I hired me.
It's interesting how negotiation is different if you're a man versus a woman. Do you take a different approach if it's a female client versus a male and it's just like, here's how you should approach it this way, or depends on the...
I take a different approach on every person.
Yeah.
So, whether you're a product leader or a marketing leader or a sales leader or you're from San Francisco or you're from Dubai or you're from New York or you're from LA, or you're German... Everybody is different culturally. So, male, female, like every little nuance is important. If you're, you know, gay or you're black... There are different challenges that everybody has to overcome.
Right? And I remember this was a powerful one. I was speaking to Chief. There were about 400 women in Chief and I'm the white dude mansplaining to all these women about negotiations. Like the scariest position for me to be in. And I remember there was this African-American gal and she said, "Jacob, should we just negotiate for 84% because that's what we're going to get anyway?" Right? Like that's defeatist. Like that sucks to have that feeling. Right? Now, I don't know what that feels like. I have done fairly well for myself and there are some advantages that I had. But I said, "Look, how many of you in here are mothers?" Many of these women raised their hands, right? "How many of you are mothers to daughters?" Right? Many of them raised their hands. I said, "Could you look your little girl in the eyes and say, 'Sweetheart, just get 80% out there'? Just go after that and do that." Right? And it kind of shocked the room a little bit because I can't compete on that level, right? I don't know what that feels like. I can't do that. But I said, "Look, if we don't learn to grow together, we're never going to solve this problem."
So, what we're trying to do here, and this is what I encourage all listeners to do, fight back. There's a big power imbalance, right? Here's the founders coming again and again. Like, "Jacob, don't tell them to do that. I don't want a revolt, right? Take care of them, right?" Push back because a rising tide raises all ships. Right? If companies want to rely on precedent, have the audacity to raise the precedent because the next people in line will do that.
To the point about collaboration, this was actually with one of your readers that read that first article we did. We made a lot of money on this deal.
And they came to you to work with you? Oh, I love this.
Yeah, so this is fun.
But so, this is kind of like a private equity hostile takeover situation. And this reader of yours was getting pushed out of the company. And if you try to go head-to-head with the PE, you're going to lose, right? He had a great relationship with the CEO, 10-year relationship. But the CEO wouldn't take any action to support him, right? Until we made it about we. The CEO had made comments that "I'm probably going to get fired, too," right? So, what we did was we talked to the CEO and we said, "Whatever precedent you help me deliver, you're going to get two to three times that. So, we need to set this up." Right? So, then they were full on. You had the CEO and the CPO putting together a game plan to advocate against the private equity, right? To support that transition plan, we got a retention bonus and a severance bonus on the table because of that. Right? Cuz now the CEO is protected as well, can point back to some precedent.
Right? So, not everybody does it out of the goodness of their heart, not in a capitalist society, right? You have to show them your motivations here are important. Right? So, women negotiating, if you want women after you to have the opportunities and better opportunities than you have, you have to have the guts to do that. And that's very easy for me to say, I'm not in your shoes, but naturally we have to be a rising tide. And there are folks that aren't going to take that challenge, and that's okay, right? Let's all push for those to help make it easier for everyone.
I love this point you made about how there's no one way to approach this. The way I was originally thinking we'd do this chat is like a step-by-step guide to negotiating. Here's what you do, 1 2 3 4, and this is how your comp goes way up. And what you told me is that that just doesn't exist. There's so many variables, there's so many types of companies, roles, seniority, people's backgrounds. Maybe speak to just like if you ever see someone telling you here's your steps to negotiate comp, it's probably not real.
That was one of the things that was hard about the article we wrote together, was that I have gains, right? It's a process that I follow. It's not a concrete step-by-step process, but one of the reasons I'm so hesitant to go this route is because negotiation comes off so complicated. It's so complicated and so academic.
When you look at the books that were written, well, Chris Voss has kind of popularized it lately, but it's like imagine there's a gun to your head in an FBI situation, and you're like, I don't have a gun to my head, I'm just dealing with my boss, and I want to understand how to do this. Or you read Getting to Yes, and it's like what you need is a strong BATNA and a good ZOPA, and it's very academic, and you're in the moment trying to have a conversation and have empathy and listen. But then you're like, what's my zone of possible agreement? What's my best alternative to... Those things are all very true, but it comes off intimidating.
Right? And when we try to focus so much on frameworks and academics, we stop listening. And that's one of the most important parts: curiosity and empathy are the two things you need to have the most. Right? If you're reaching a block, why does that block exist? If you don't know the answer, you haven't asked the right questions. Right? You don't necessarily know. It's an information imbalance that you have.
And really what negotiation comes down to is information and timing. That's what creates power. Right? Those are the three things. That's all you need to know. You have to have the information. When we were talking about that game of Werewolf, even when you're outnumbered five to one, if you have more information, the odds are you'll win. Right?
So, I don't want it to be overly complicated. I guess I have to say it. So, I'm trying to write a book this year. I'm going to write it, right? I'm going to write it.
It now must happen.
Now it must happen. I know, like I just kind of clenched up a little bit cuz I got to do it.
It's still early in the year. You got so much time.
Oh, yeah, thanks. All right. I'm a prolific writer. I'll get after that. But the book title is called Predetermined. And I wanted it to be Predetermined with a question mark.
Right? Because none of these outcomes are predetermined. No matter what situation you are in your life, how you were raised, it could be more difficult for you, but it's not predetermined. And it's one of the reasons I love this work, is that I don't know what the outcome can be. We don't know. You should never be so sure, because then you start putting a ceiling on your life.
And one of my favorite things to ask somebody, and they're like, "Oh, Jacob, I want to do this in 5 years." I say, "What would that look like if it was done in one? What must be true?" I'm like, truncating that experience just to think through it. Not necessarily that I'm asking them to rush through it or whatever.
But I have clients that they'll have 10 or 15 million dollars in the bank and they'll be in their late 50s. And they're like, "Oh, I need 10 or 15 more to retire." What? What do you mean you need 10 to 15? Like, if I had a million dollars, I would retire. Like, give me a break. Like, that seems like so much money to me. Why is that the case? Right? So, I like to challenge those notions there, right?
It's an important thing to think about. Like, it's not as step-by-step as it needs to be. Cuz sometimes, another one of my favorite questions: what would your life look like with less? Maybe a minimalist or stoic type philosophy.
One of these Hollywood deals we did, we had a director and a Marvel superhero that got in a spat on a big franchise. This is an estimated 500 million to billion-dollar franchise opportunity. This A-list celebrity and their writer on this third installment of a movie didn't like it. So, think celebrity kind of being a prima donna. I hate it. I don't like the direction it's going. They're not writing me right. Fire him. Right? Offended the original director, cuz they wrote the first two movies and they were very successful, right? To build this franchise. So, pissed off, right?
Next writer comes in. This is worse than the one before. Can we just hire back the first one and get work through it, right? So, 6 months later, money, production delays, all that. Go back to that original writer. And the agency's like, "We got to throw money at this guy." Like, to get him to say yes. Like, here's a million more dollars, right? Didn't do it. Like, a million dollars wasn't enough to mend this relationship. The important lesson here is it's not always about money. That individual was making $10 million a year. A 10% increase to have to go back to somebody they didn't like, not powerful.
Right? My suggestion was, can you ask the actor, this A-list celebrity, to humble themselves and apologize? And that is what moved the deal across the line. Actually came in and apologized for the behavior, it's not going to be like that. That's what got the deal back together, and the million dollars was saved.
So, it's not always about money. I use a lot of money in the stories because it's kind of shock and awe. It's like, wow, like that's going to have big impact. Like, at the end of the day, if you're making $18 an hour and you negotiate to 24, like, such a material difference in your life. That is so magical, to maybe be able to afford gas for the first time. Right?
And then I'm telling stories where people haven't thought about how much gas costs ever, right? So, like, there are situations I remember that. I just, 10 years ago, well, 12 years ago, I was homeless, like fighting through all this stuff, and didn't know if I could pay for gas. So, it's one of the reasons I'm inspired to do that. Is that you can make a material difference and it compounds throughout your life, but it's not always about money.
I want to follow this Hollywood thread before we wrap up. I love that you work with Hollywood folks, celebrities, and also tech people, which is most of the audience here. Is there another wild story from your Hollywood life that might be fun to share?
I think what's interesting about Hollywood is that it's so far-fetched. And you were talking about what happens when offers get rescinded, right? And before I was working in Hollywood, I would have tried to talk people into asking for $20,000 more, right? Which after taxes is like eight, right? And then when you look at it, it's like $400 a month or whatever, that you're struggling to maybe ask for 10,000 grand, right?
In Hollywood, like, we did this deal with, I can't share who, A-list celebrity. And the company said, we want to pay her $5 million for this movie. And the attorney came back, we want $22 million. Like, talk about being aggressive. Right? And the production company is like, all right, how about 13? And this was in like a 2-day span. So they went from $5 million to $13 million in 2 days. And the other, they're like, well, instead of 22, how about 18, right? Like, they're moving $4 million chunks at a time. And we're over here on tech going like, oh, I wonder if I can get 10,000. Right?
So like, that's something that I just find absolutely wild. The bigger the... Like, this is just like, you want to make money, solve rich people problems, right? That's what happens, right? It's just escalated. I can only imagine what a negotiation with like Elon Musk would be like. They'll throw 100 million at it. And you're like, oh my gosh.
Like, I also found out that a million seconds is like 11 days. Have you ever heard this? A million seconds is 11 days. Do you know how long a billion seconds is?
Like probably hundreds of years.
It's like 30. 30 years.
31 years. So between 11 days... That's the discrepancy between a million and a billion, right? And so these are just like, these things scale so exponentially. It's just that what you say and how you negotiate just kind of changes. So if you want to really increase your comp, you do have to move rooms. Right? You have to start networking and making connections with folks that can do that with you.
Maybe as a last question, just to get very tactical. Somebody that maybe is about to get an offer, got an offer, will get an offer in the near future. What's the first thing they should do to help them increase their comp? Is it just reply with, is there room for more? What should they do when they get that email?
Okay. You always give me these nuanced ones, huh? So, they get it from the recruiter or they get...
Yeah, let's say the recruiter's, it's probably where... Yeah.
Recruiter's going to, again, they're probably going to have that 20% with a room there. If you're okay with that, I might, again, just say, what's the chance we can bump? Like, this is what I was looking for. Right?
I would probably, knowing that the recruiter is going to split the difference, I would probably anchor higher versus lower. There have been some studies, and I was reading some, I've read a lot of negotiation books. There's like one from the 70s on these negotiation games, and those who anchored egregiously high won 75% more than those who just try to be reasonable. Right? So, it's like, look, I was hoping for 150,000 more. Sometimes you get 70. Right? Sometimes you get 50. But if you ask for 50 more, you would have got 15. Right?
So, if you are going to re-anchor, just say, hey, I was kind of in the ballpark at this. Again, with the nuance, you may have already committed to a range before, and it can be difficult to have that conversation. Right? So, I might say, hey, after we've had the conversations with the hiring manager and yada yada, it sounds like the scope of the role has increased. Are you open to revisiting the comp structure on this? That's likely how I would respond.
If the recruiter says this is all we can do, and you have the audacity to do this, I may send a text message or an email to the hiring manager and say, hey, we're almost across the line. It sounds like we had a sticking point. Are you open to have a conversation? That's who I want to close with. And I don't want to put the recruiter down. You say, it just sounds like we're at a sticking point here, and I'm really looking forward to working with you. Are you open to chat real quick? I don't need to have a big laundry list of, I'm going to do this for you and I'm going to do that. Like, that will not work.
And I've noticed this in our back and forth in your emails. Like, you'll respond with two words. That's all you need. Right? You don't often need more. So, like, the more confident you get, the shorter your communication gets. And sometimes it can be as simple as texting the hiring manager saying, "Open to chat." You don't give them any reason. It's just, open to chat. And then you control the conversation from there.
Hopefully that was tactical enough. If it's not, I have a lot of written scripts that are out there that you can copy and paste, so you don't have to just rip the transcript down from all of Lenny's videos. Right? I do have written scripts and guides for this, and I have a free course on how to do this, too, that's on YouTube. So, if you need the actual specifics, there are a lot of scenarios I've already kind of covered you can go to.
Amazing. And we'll link to all that. And I asked you what you were hoping to get out of this before we started recording. And just to be clear, you're not looking for new clients. You're booked up. You share all of this stuff out there. You have this free course. You have all these Substack posts. So that's what I love about you. It's not like, you know, you're trying to... It's not like some deal lead flow here.
My mission is to make what I've learned from very successful people more accessible. Right? And if you put a pay band on all of that, you're not making it accessible. Right? My hourly fees are very high. Right? So, it's like, I don't want to push for that and feel like I'm unobtainable. So, I want to give away as much as I can. And these things shouldn't be gatekept. They often are.
But yeah, as I mentioned a little bit in the green room, I just felt a little powerless growing up. There was like some little substance abuse and trauma as I was growing up, and I never felt comfortable or safe. And so, when I became a little older, I started to understand psychology a little bit differently, because the same fear I'd have as a child, I could see in the boardroom. I could see the same fight or flight mechanisms, but that was far less scary. Right? So, it's just money. Money's like, I'm not going to get hit. Right? Nobody's going to get hurt here. Right? So, I could start to see that, and I could see the body language, and I can understand when somebody was in a tense moment. And all I ever wanted to do, because I felt that from a little kid, was help that person feel safe. Right? Help them feel safe in that moment. And so, I've been obsessed over how to solve that for my entire career. First for myself, and then what became natural for me is for other people, cuz I could see their growth, and that's what became most fulfilling.
There's a whole other conversation we could have about that whole part of your...
We got to be careful about that one. Yeah.
All right.
That one I might start crying on that one.
Okay, well, that makes good content. That could be part two. Jacob, you're...
...comments. Like, next time make Jacob cry, Lenny. Go for the kill. Go for the kill.
I hope not. I don't think my people want that. We'll see. Oh my god. Okay, before we get to our very exciting lightning round, Jacob, is there anything else you want to share, anything else you want to leave listeners with?
Just that if you're going to take a chance, take a chance on yourself. I'm sure a lot of these folks are parents, and you want to be the best version of yourself and show your kids that you could survive anything. You're going to get a couple bruises along the way. Right? Like, these are great first world problems to try to fight for. Right? Like, it's not going to take away your home. The thing is, you're only going to make life better around you. Right? If your cup overfloweth, right? You'll be able to give more to others.
So, it's not about, am I worth it? It's like, if you are a generous person naturally, you can be more generous if you have more wealth. Right? If you're afraid of wealth, this is something that really screwed me up. Like, I used to despise wealth. I despised it. Right? And I don't know why. It was like, I didn't trust people with money. I felt like they all had to be dirty or they all had to do something, and to be fair, a lot of people do things that are highly questionable and unethical, right? And we see that in the world around us. But if you fear it and you don't understand it, you'll never have an opportunity to change it.
And so you need to take some chances on yourself with this, and hopefully that's another piece, just having the confidence to go out and try. Even if you fail, you're failing forward, you're learning. Right? And you're going to find a style that works best for you. It's not that Jacob Warwick's style is the style that's awesome, or Lenny's style is the style. You don't need to copy anyone else. You need to find that center that works well for you and what you're comfortable with.
That is beautiful. I'm also realizing as we're talking, we haven't mentioned AI once in this conversation. It's like...
Which is incredible. I love that.
The listeners are like, oh, thank goodness.
Yeah, that's how I feel.
Goodness.
Just once in a while.
It's cuz I don't want AI to replace me, Lenny. I don't want it.
I... Yeah, I don't even know. Anyway, we're getting to... Okay, well...
...you speechless. That's the job. If you get the podcast host speechless, you're doing your job. That's great.
Okay, well, we did it. With that, Jacob, we have reached our very exciting lightning round. I've got five questions for you. Are you ready?
All right, I'll do the best I can, yeah.
Here we go. What are two or three books you find yourself recommending most to other people?
Influence by Robert Cialdini.
Sweet, that's the one.
That's the one. I mean, I like Herb Cohen's You Can Negotiate Anything. It's a little dated. Like, old white dude in the 80s dated, so be mindful it doesn't suit all audiences, but what I like about it is they talk about like negotiating dishwashers and stuff, not like going to market with Meta versus Instagram and the acquisition. Like, it's not complicated. It's like, here's an apple and here's an orange, and here's the concept of negotiation really spelled out simple.
I did just do a podcast with John Lowry, and he wrote a book called Negotiation Made Simple. And I remember reading it and I was pissed off, because I wanted to write a book a couple years ago, and then I read his and said, like, this is what I wanted to write. So I was frustrated, and then I was like, I'm going to reach out to him, because I have a lot of respect for him. So I did his podcast, that'll be live soon, but yeah, that was Negotiation Made Simple. It really breaks it down in an easy way, and I think that could be like a bible.
And then I like Radical Candor. I know some of your guests put that on. I've met Kim Scott, she's phenomenal. Like, Radical Candor really gave me the confidence to be assertive in the ways that I never had been before. So my wife taught me that, Kim Scott embraced it in the corporate world, and those two pieces really helped elevate my career.
I think Radical Candor is the second most mentioned book on this podcast, behind High Output Management.
Yeah, I have not read that. Admittedly, I'm bad at consuming content. I only create. I've got this rule that you create 10 times more content than you consume. So I read like one book a year, and now apparently I'm going to write one book. So maybe that'll be the new goal.
That's a great framework. Okay, next question. Do you have a favorite recent movie or TV show you've really enjoyed?
I've been really liking watching Luca. The Disney movie.
Having a toddler and a newborn, I really just watch cartoons now. So I actually, for low-stimulating things, I really like Minuscule.
It's like a YouTube short that's like French made and it's like spiders and flies and like bugs. Just very low stimulation hanging around.
That sounds not appealing, but...
No, that's why it's so good, because you're so overstimulated having kids that it's so mellow. You can be like, oh, I actually get to think a little bit. You know, like...
Okay.
You know, finding a little boredom and creative. Like, that's how you get creative. If it's like Cocomelon and PAW Patrol and you can hear the beats in your head, you can't do that. I can't do that to my kids.
Favorite recent product you've discovered that you love.
Claude CoWork. I mean, I...
Good one.
I love Claude CoWork. I'm sorry for mentioning AI, but I really only use a handful of products, so Claude CoWork is one of them, and MacroFactor for macro tracking, and I got a Whoop this last year and I've lost almost 50 lb just paying attention to my Whoop stats and trying to sleep. You could tell I'm a pretty obsessive guy, so data still geeks me out a little bit on that. But those are the three products that I would use every day, and a little bit of Gemini, too. Those are the two, in my opinion, winning the race.
Do you have a favorite life motto that you find yourself coming back to in work or in life?
Always give more than you expect to receive.
It's like a golden rule plus plus.
That's how networking works. You don't network with someone trying to take. You say, how can I help you? And that's a principle from Cialdini also, right? And How to Win Friends and Influence People, right? That's not why I do it. I'm just suggesting that's also an area where you can read more on that.
Final question: you're starting a foundation. A non-profit.
Yeah, I'm on the board of the Cody Dieruf Foundation, and that's in Bozeman, Montana. And what we do is... my son has cystic fibrosis. Yeah, and cystic fibrosis is a genetic condition. I'll actually talk a little bit more about it in Predetermined, because his life was, quote, predetermined. We were not really accepting that. But with our foundation, we help rural parts of Montana get access to the health care that they need.
Yeah, and so they got me with this. So we helped this family, this woman, she had three boys. This is a sad story, so bear with me. So one of her boys, 29 years old, needed a lung transplant. This is what cystic fibrosis does. So made it to 29 is good. The life expectancy used to be 7 to 10 years old. So made it to 29, needed a lung transplant. She couldn't afford it. And her son passed away. She had two other boys with cystic fibrosis. And then her 27-year-old son, 2 years younger, needed a lung transplant. And she actually found out that our agency existed in that period. And we funded the life flight to Denver Children's Hospital to get that life-saving surgery and saved her son's life.
And that sounds like a great story. The part that got me was that now the mom feels all this guilt because she could have saved her son's life if she knew we existed. And that part, like, I was in tears thinking about that.
I have talked a little bit about my son's diagnosis. It's not defining our life, but my wife and I prayed about this, and it was: if it would happen to anyone, it should happen to us. Because as soon as that happened, I made a handful of phone calls. I did all this networking to be selfish and build my career and do these things, and in that give-before-you-ask-to-receive philosophy, I've always kind of lived by that: undersell, overdeliver. And within 24 hours of his diagnosis, I had a phone call from the chief medical officer of Denver Children's Hospital, at Stanford, and I got a call from the FDA that said, don't worry, your son's medication is getting lowered to one year old, and the Trikafta is going from six to two. So he may never experience a symptom in his life, because this has changed now. So I felt this immense blessing and support through that.
So that's the foundation. We support these rural areas that don't have access to that health care. And then I've also started conversations with the Cystic Fibrosis Foundation, which really helped fund the life-saving medication that changes the life expectancy from 7 to 70 years old. They are expected to have full lives now. So that's something I'm very passionate about.
Incredible. Oh man, there are so many topics and directions we could have gone with this. Jacob...
I know I blew you out of the water, man. Sorry. Yeah, I monologue like nobody's business.
I've had worse. Okay, where can folks find you online if they want to reach out, maybe follow up on some of this stuff, and how can listeners be useful to you?
Listeners can be useful just by advocating for themselves. Rising tide forever. That's important. I guess I don't really have social media. I deleted LinkedIn. The post I wrote about that kind of went viral on Substack. It's cool. I think I shared that one with you.
I have execsandthecity.com, which, yes, is a play on Sex and the City. It's kind of explaining some of the things that people are afraid to talk about. So Execs and the City is my Substack. And I write once a week on Thursday morning, and I share little thoughts on what's happening. Occasionally I'll share case studies on what clients have done. I'll share play-by-plays and the actual scripts. That's also where I have a free job search course. It's about 8 hours that I filmed, and I sold it for like a grand, and now I just give it away for free. That's also available on the YouTube, which is Execs and the City, which has like 100 subscribers, so don't expect a lot of content from me. I'm not pumping out video content all the time.
And then there's a small paid tier if somebody wants to get discounts on coaching. They also get access to Jacob GPT. Well, it's another AI I mentioned. It's digitally trained on... I think you have one, too, right?
Yeah, Lenny bot.
...my content. Lenny bot. Yeah, so it's like a Jacob bot, which is a minor Lenny bot, right? Trained on my content. Yeah, and then I do some additional case studies for them. And then my actual business is thinkwarwick.com, which just tells you outcomes that we've been able to deliver. So I'm not going to ask you for Instagram or anything like that. Just real simple. Try to keep it at Substack only, really.
Jacob, this was awesome. Thank you so much for being here.
Thank you, Lenny. I appreciate the time today, and again, I was real giddy about it, and your motto was to have fun. I had a lot of fun today. Thank you.
That's right. Here we go. People don't see this if they're waiting till the end of this podcast. I have this little pocket I show all the guests that our goal is to have fun. So, Easter egg. All right, Jacob, thank you so much. Bye, everyone.
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
Article published · Updated