The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick

Lenny Rachitsky (00:00:00): What’s the most common mistake that people make when they’re negotiating their comp?

Jacob Warwick (00:00:03): 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 is in the airport security line and pissed off and they read it, they might be like, “That bastard wants more money.”

Lenny Rachitsky (00:00:18): 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.”

Jacob Warwick (00:00:24): But when you look at the money that the company’s making in comparison, 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.

Lenny Rachitsky (00:00:37): The core to 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 me this much more.”

Jacob Warwick (00:00:44): These companies have significant leverage over it. 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.

Lenny Rachitsky (00:00:58): 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.

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(00:04:16): Jacob, thank you so much for being here. Welcome to the podcast.

Jacob Warwick (00:04:20): 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… and it’s going to be a great chat. So I’m very excited. Thank you for having me.

Lenny Rachitsky (00:04:34): 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’ve personally been very, very bad at in my career. I don’t know if I… Maybe one time I pushed back and negotiated a higher comp, but I just have always been really nervous to do this and just really bad at this, 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.

(00:05:19): Most of the people you work with, just as that 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 keep people… or frame a reference. How much comp are people generally leaving on the table when they don’t even try to negotiate?

Jacob Warwick (00:05:36): 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. 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 pushback, which is, when you’re making that kind of money, that’s life changing. I’ve noticed that when you make $1 million W2, same pushback, 20%, sometimes more, just on the, “What’s the chance?” depending on how well you navigated that interview process.

(00:06:18): 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. Those that challenge authority and challenge in a meaningful and collaborative way will win more than those that don’t. What’s interesting is I’ve found that product, 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.

(00:07:28): You’re looking back at your career and say, ” 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. That’s just a simple ask, and even that, 20, 30%.

Lenny Rachitsky (00:07:54): 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 they join… They get better comp and then they’re like, “Oh, everyone can… They know that I pushed all this and I’m this kind of greedy person, and now the expectations are higher.” What do you tell people to help them get past that and actually negotiate and actually go for it?

Jacob Warwick (00:08:22): Yeah, a couple things here. So, first of all, usually a company is extracting much more value out of you naturally, like 5 to 1, 10 to 1, 100 to 1. I know the audience is primarily product here. You’re developing products that have infinite scalability in some capacity that’s going to make the company a lot of money, and you’re a big piece of that. Product tends to be rewarded fairly well. But when you look at the money that the company’s making in comparison, 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.

(00:09:14): 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 hellaciously for the top of the band or break the bands just because you can. This isn’t to be greedy, but it’s just to understand that this value exchange isn’t fair for you regardless of how it works. The path to wealth is through ownership. And as a W2 employee, you’re being taxed heavily, and it makes sense to push a little bit in this context. That’s typically where I start. I want you to just have the confidence to know that it’s okay.

Lenny Rachitsky (00:09:47): 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 or 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?

Jacob Warwick (00:10:07): I will challenge them as well. Now, how important of a priority is top talent and maintaining and retaining top talent to you? When we’re thinking about how quickly the speed of innovation is happening, you’ve had a lot of great AI guests on the channel recently, right? 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 because it’s very expensive to replace them. I’m not suggesting that people beat you up for the sake of beating you up. This is a myth about negotiation that’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 makes sense there.”

(00:11:03): 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… We are getting more creative here. 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 because it’s hard. It’s hard to make this. Everyone also thinks they’re top talent. And when everyone thinks they’re top talent, somebody’s got to be lying. It can be difficult to understand that. So those that I’ve 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.

(00:12:09): I have started to have these conversations with a couple of 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, 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.” I’m not suggesting give everyone everything in the company and totally ruin your business model. But if you want to be competitive, be competitive with your pay as well.

Lenny Rachitsky (00:13:04): That’s a great answer. 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.

Jacob Warwick (00:13:16): 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. They don’t know that they 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.

Lenny Rachitsky (00:13:53): 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.

Jacob Warwick (00:14:02): I would call it fingerprintless, and there’s a reason for this. It’s not yet popularized. Maybe it will be with some of these in AI ICEs, and these hot scientists are 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 the corporate America right now. Now, if that happens, it almost dilutes the leadership and presence of the executive. So how I work is similar to an attorney where all correspondence goes through me before it goes to the end recipient. 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.

(00:14:59): 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. Haste equals risk. 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.

Lenny Rachitsky (00:15:36): This is so interesting. What’s the most common biggest mistake that people make when they’re negotiating their comp?

Jacob Warwick (00:15:43): They don’t understand when it starts. It starts much sooner than you think. I’ve got myself on hot water with this before too because a… A LinkedIn profile in your resume is a snapshot of what you’ve been in the past, but it doesn’t help you negotiate in the forward. 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 moving forward and what your visions are and things like that, so they stamp you as Product Manager Lenny. Now, you’re media mogul icon, whatever, but there’s a gap that you have to fill. 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. You can see… It was wildly consistent. It was almost frustrating.

(00:16:40): 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. 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, 225, that sounds fair.” Five 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.

(00:17:32): 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 we’ll hide behind the easiest communication channel as possible. I might email you my demands 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 is 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 as clean as it can be, if you catch them at the wrong time, you have no control over how it’s received. 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.

(00:18:32): Oftentimes, we also try to negotiate through recruiters. You could do that… 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. 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. Some people might also have a concern with, “Well, how do I go around the recruiter? I don’t want them to look bad.” We have to do that respectfully and now we need to plan what that communication looks like. 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.

Lenny Rachitsky (00:19:31): I love how tactical we’re getting here. Following this thread, the advice here is when you get an offer and you want, and you should… 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.

Jacob Warwick (00:19:54): There are situations, especially at high levels, more deals are closed on the golf course than they are in a boardroom. There are situations where you pull someone into a different element. This is called home field advantage. So if you go to a company to have a conversation, you are 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 AM and 1:00 PM. I want a meeting in that time,” so I will say, “I’m unavailable until that time becomes available.” That also communicates scarcity and that you won’t get pushed around. It’s scary to do that, to say, “No,” to the CEO, “I’m actually only available here,” but that also creates a rubber band effect that makes you more attractive.

(00:20:55): 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. So they used to walk outside of the office and just walk downtown San Francisco instead. 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.

(00:21:45): 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 the biggest startup you’ve ever seen. I used to joke that it was two midgets in a trench coat pretending to be a real company. 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 a 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.

Lenny Rachitsky (00:22:24): So the advice there is try to get this conversation out of their office.

Jacob Warwick (00:22:28): It can be. But if I’m a product manager and I’m talking to a director, that may not be possible.

Lenny Rachitsky (00:22:29): Right.

Jacob Warwick (00:22:34): Right? You might just say, “Look, you got to come into the office. You got to do this.” I’m pushing… 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 questions. Are you open to take a walk down AT&T Park and have a conversation about it?” If 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.

Lenny Rachitsky (00:23:05): 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 the step by step you’d… And I know this depends on the role, seniority, type of company, PE, VC, back startup, because 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, because that feels so scary?

Jacob Warwick (00:23:42): So, first, we want to approach with gratitude. We’re thankful that we want to move forward, so, “Lenny, I appreciate you making me an offer. I’m excited to work with you.” We want to show enthusiasm, which also shows some confidence. We have to show that the deal’s going to get done even if you’re on the fence about it. 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, so, “I’m grateful. I’m looking forward to working with you. I want to review this over the next couple of days, talk to my wife about it, 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, employment lawyer, all that. That stuff is expected.

(00:24:28): 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, but we’ll loop back and it shouldn’t be a problem. I imagine we start working together in a couple weeks.” The point is you have to sell that the deal’s going to be done, which helps them feel like it’s going to move forward regardless. 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 at 40%,” or anything like that.

(00:25:03): Now, this is where a lot of nuance comes in. We might say, “Come back three days later, want to have the conversation, let’s take a walk in the park and talk through it. I 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.” 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?” Or they may say, “We comped you in the middle part of the range.” You might say, “What does the top end look like? What must I do to fit those needs for you? Can you help me understand?”

(00:25:47): 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 overleveling that’s happened. There are people that are C-suite going back to VP, and VP is going back to directors, especially as they go to bigger companies. Oftentimes, I’ll say, “As we had this conversation, I’m likely a little more horsepower than you anticipated. What’s the chance we can come in and restructure the comp for the type of talent we’re bringing in here?” This is a line that we used. There was 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.

(00:26:53): I could 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. This is how bigger moves happen. It doesn’t mean you can’t push for maybe 20% more naturally. In that, I would start with, “What’s the chance there’s a little bit more here? I was expecting this.” Again, more nuances because 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?” 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.

Lenny Rachitsky (00:27:40): 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 the soft pushback just to see?

Jacob Warwick (00:27:51): 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. When you anchor, that’s the ceiling, and what often happens is naturally they want to split the difference.

(00:28:15): There’s a quick Hollywood story here. We had a writer who had a $700,000 contract, so 700, and the agent that I was working with was saying, “This writer has the most aggressive attorneys in LA. They’re super aggressive,” and I said, “Well, how do you know, first of all, if that’s what they’re perceived as?” The production studio offers this writers 700. The attorneys come back and say, “We want 1.3, 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 they split the difference right in the middle. So if the attorneys-

Jacob Warwick (00:29:00): 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? How do we know?

(00:29:15): 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. So it still made the client 300,000. They were excited. 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.

(00:29:36): So those are things that you’ve got to slow down to really understand where is the value being made here? And that movie, that movie could make $50 million. You think one million for writing was worth it for 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. 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, two and a half million more. So performance-based triggers.

Lenny Rachitsky (00:30:18): I love just how much you love this. It’s just clear this is so interesting to you.

Jacob Warwick (00:30:23): 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 knew 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.

Lenny Rachitsky (00:30:50): On that note, do these tactics work on kids and wives? Is this something that translates?

Jacob Warwick (00:30:57): 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.”

(00:31:10): And toddlers are terrorists, so I haven’t figured that one out. I’ve resort 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.

Lenny Rachitsky (00:31:24): I would pay a lot of money for a version of you for toddlers. Oh my God. It’s like I try to negotiate with the other kid.

Jacob Warwick (00:31:24): I think we all would-

Lenny Rachitsky (00:31:31): I’m like, “Three minutes.” He’s like, “Six.” I’m like, “Four minutes.” “No, six.” He never budges [inaudible 00:31:39]-

Jacob Warwick (00:31:39): “Five minutes.” He’s like, “Eight.”

Lenny Rachitsky (00:31:40): Yeah, exactly. Although sometimes [inaudible 00:31:43].

Jacob Warwick (00:31:42): My son does that too. I go, “Do you want a binky?” And he goes, “Five binkies.” And I go, “I don’t know if we have five,” and he’s all, “10 binkies.”

Lenny Rachitsky (00:31:52): Whatever you need, I’ll get it if you go to sleep.

Jacob Warwick (00:31:54): Yeah. Yeah, please sleep.

Lenny Rachitsky (00:31:56): [inaudible 00:31:56]. Yeah. Yeah. We need this for toddlers. I would subscribe. Okay, so-

Jacob Warwick (00:32:01): Ms. Rachel’s the closest thing we got.

Lenny Rachitsky (00:32:04): Yeah. Okay, so coming back to this compensation number, so you’ve touched on this a bit, and I think this is an important part of your advice is 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?

Jacob Warwick (00:32:19): 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. 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 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 is that what got you here won’t get you there. So things start changing as you mature in your career.

(00:32:57): 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. It’s very difficult to optimize for inbound attention the higher up you go unless you become very popular. And then what happens is you share less information because people come to you in a different capacity.

(00:33:20): 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.

(00:33:40): So typically, I’d recommend you answer, right? “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 kind of 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?

(00:34:06): Now, it’s 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, right? So culturally, there’s a lot of differences in how this conversation happens.

(00:34:22): 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?”

(00:34:35): 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 up marketing managers and I saw that they made 60 grand a year and I suddenly got offended in how little money I was making. 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.

(00:35:02): So when a recruiter called me, I pulled that. I didn’t want to tell them I was making $14 an hour. They’d be like, “Who is this kid? He’s not very good. That’s 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.” 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 that.

(00:35:27): 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 go away of not liking my job. Turns out that was a fool’s errand, but that’s a story for another time.

Lenny Rachitsky (00:35:37): 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 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, “Well, it’s not worth it. We’re going to move on.” Has that ever happened? What are the odds that might happen?

Jacob Warwick (00:35:58): A couple things about power. So if you have the ability to say no, you have infinite power. Right? 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 something. Right?

(00:36:14): Now, this isn’t to shame somebody who’s feeling that way. If you’re out of work for six weeks in San Francisco, you’re homeless. That’s just the reality of the situation. So if I got to say a number to get a job, I think 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?

(00:36:34): 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 uncomfort of being out of work six months, 12 months, 18 months, you have an identity tied to a chief product officer role or a 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.

(00:37:10): So we give into 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.

(00:37:29): So can it get frustrated? Absolutely. But if somebody disrespects you through that process, doesn’t that give you an indication of who the company’s working with? 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.

(00:37:48): And one behavioral psychology hack here is we give someone a positive reputation that they want to withhold, 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’re 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?

(00:38:23): Another option, you don’t necessarily know if you’re the best solution for that fit or not. 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, and 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 and 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.

(00:38:51): 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 [inaudible 00:39:01] it was 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. 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 six months later, I landed at VP for a quarter million. That was my first realm into VP. The initial offer was for content manager. So they 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.

Lenny Rachitsky (00:39:53): Along these lines, I want to touch on, it feels like maybe the core approach you take, kind of the core to your philosophy, which is to kind of 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 me this much more because it’s such a big problem for you.” Talk about just that mindset.

Jacob Warwick (00:40:19): 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. There’s always so much more that’s not documented. Right?

(00:40:44): Now, when you’re going into a position and you see a JD, you’re like, “Yeah, I could do all those things,” but there’s so much more. 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.” This is fair. Then you go through the process of the interviewing, 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.

(00:41:17): 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 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. So that’s why we don’t want to anchor too early, we want to understand.

(00:41:43): 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. 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 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.

(00:42:19): 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.

(00:42:34): So through the process, it’s a discovery process. Why am I here? What gets you excited about me? That’s how we start a conversation. Too many interviews start with, “Tell me about yourself, tell me about this 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.

(00:42:56): 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.”

(00:43:13): 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?

(00:43:36): So I want to clarify why I’m in the room with you. So we do that as a PMO. Sounds like, 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 has been a problem and we need to shift towards native AI. Is there anything that I missed? Then they’re revealing information, you take control of that conversation. And then we want to share, 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 that 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?

(00:44:21): So I want to ask all these discovery questions. They’re like, “Oh, look, it’s a $10 million problem where we’ve gone through five different PMs in six months,” and you’re starting to understand where the dirty laundry in the company is. Then we get to sell the vacation. Then we get to say, “Look, all right, so fast-forward six 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 board meeting next, 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 forced them to visualize a utopian situation and who was right next to them doing that? I was.

(00:45:17): 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 instead 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. So when I push back, the likelihood that I break the rules is significantly higher than if I hadn’t done that.

Lenny Rachitsky (00:45:45): This is amazing. So trying to just summarize what you’re sharing here, and I think it’s important for people to also note, you can do it in your own words. This is likely not something you’ll just be able to pop out and do. This is something that takes time to do well and it feels awkward probably. And that’s why people work with you that you 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.

Jacob Warwick (00:46:07): It could be tricky to understand where your value is because you’re so close to it. You just do this every day. And for 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.

Lenny Rachitsky (00:46:45): 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 like understand the landscape of where you could bring tons of value. Help them see that, like, “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 described it as sell to vacation, help them visualize, okay, now that this is solved, how awesome would that be? And part, there’s like all this psychological stuff you’re throwing in there, just like how [inaudible 00:47:25].

Jacob Warwick (00:47:25): Yeah. I can really make this concrete with a quick story.

Lenny Rachitsky (00:47:27): Yeah. Let’s do it.

Jacob Warwick (00:47:28): 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?

(00:47:57): So every agency wanted to sign this hot director who just did this billion dollar deal with, people already know who it is. So my client, the agent asked me like, “We got to sign this. It would be stupid to go to any other agency. We’ve done this, we’ve done that, we’ve represented Julia Roberts and Matt Damon,” and all this, just naming, name dropping, right? Now, this is actually a problem because if we’re leaning on logic and credibility, we’re losing. We need to sell the future and own the emotion.

(00:48:29): 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 an 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, and did you see I have three 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?

(00:49:08): So in this deal, we get into the meeting, it’s a big day. And I said, “Schedule the appointment already, work with the assistant, schedule the appointment with whoever it is it needs to be. It needs to be a big name person.” So we go into that interview and inevitably the conversation goes, “Why should I sign your agency?” 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.”

(00:49:43): 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. 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.

Lenny Rachitsky (00:50:09): 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 like, try to even do it. It sounds like you could just do it.

Jacob Warwick (00:50:24): If you 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. So they might say, “Oh, I’ve been interested in getting to Google,” or whatever. Let’s say they’re in product. I said, “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 with them. “Just hold on a second, hold on.”

(00:50:49): 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 touchpoints where I can make sure that that person is following through. I can get a 360 degree 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.

(00:51:27): And in this instance, if you want to role play with me for a second, something that would be really exciting, like 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, 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?

Lenny Rachitsky (00:51:58): I immediately love this question as a … It sounds to people like this is manipulative in … 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 and I want you to be focused on this and I would do a lot to help make this happen.

(00:52:17): 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, they’re like, “This is the best thing I’ve ever heard around comp.”

Jacob Warwick (00:52:28): 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, sometimes I’ll ask, or an introductions come to me, 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’s an asshole? I’m curious.”

(00:52:51): And sometimes I just make a complete reframe so there’s no other option. Well, I’m obviously not going to say you’re an asshole, 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 to be like, “This guy’s a total manipulative jerk.” I will say, I hope that you use this for good and not evil, but this is just the way power works.

(00:53:14): 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. Too many YouTube videos are like, “Oh, like and subscribe.” And that’s all they do, 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.

(00:53:59): 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?” 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 can better control outcomes.

(00:54:21): It’s the same, interview process. When you go back to your committee, are you going to say, “Jacob solved X, Y, Z and we’re excited. Slam dunk, let’s move forward.” And I like really quickly, slam dunk. Right? Easy to remember. Or are you going to say, “There’s a couple gaps here in 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. And I 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.

(00:54:57): 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.” If you close the next conversation, you don’t give up necessarily. That was another monologue, but that was a little bit inside the mind of how I think about these things.

Lenny Rachitsky (00:55:32): No, this is so awesome. So if you think about a hiring manager, having someone like, I don’t know, just 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 because I know that these are big challenges for you right now.” If I was the hiring manager, I’d be like, “Holy shit, this is awesome. I just need someone to come in and solve these problems for me. This is why I’m hiring.”

Jacob Warwick (00:56:01): And you better deliver. Right?

Lenny Rachitsky (00:56:02): And you-

Jacob Warwick (00:56:03): And that’s the other thing. It sounds like if this guy can’t deliver, it’s not going to happen. Or if this gal can’t deliver, that’s frustrating. I’m not suggesting go so far outside of your comfort zone that you feel like you can’t deliver because that reputation will haunt you. You have to really understand.

(00:56:21): 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 of that. 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. 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.

(00:56:54): So you could say, “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’ve truly asked the right questions to understand.

(00:57:18): 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 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.

(00:57:48): 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 putting companies up and to the right.

Lenny Rachitsky (00:58:02): I like that you went there around don’t-

Jacob Warwick (00:58:00): … putting companies up into the right.

Lenny Rachitsky (00:58:02): I like that you went there around, “Don’t overpromise because it’s easy to say. We’re going to solve all your pain for you. I’m going to be the best thing to ever happen.”

Jacob Warwick (00:58:07): You never under promise, over deliver. Always. Under promise, over deliver.

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(00:59:02): 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 about 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 get there?

Jacob Warwick (00:59:23): Yeah. Part of my hat is hype man hat. You got to be hype man to a degree. And I work with some of the most privileged and successful people in the world. 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.” At least financially. We could debate about the ethics of the companies they work for and those things.

(00:59:44): Now, most of the decisions that you’ve made in your career have made you a top 10th of a percentile of the earners on the planet. Don’t tell me you’re not confident. You can’t pull 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, a 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.

(01:00:10): 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 user’s 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 the term I use a lot, which I know product leaders will use also.

(01:00:39): We want to eliminate friction. 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.

(01:01:04): And again, it’s not just product. 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 maybe I’m not as gregarious and maybe I’m not a six-foot three tall white dude in California who’s got the sales persona and he’s got that extra version. I’m not that.”

(01:01:41): Don’t be me. Don’t be Jacob Light. Be you, your authentic you, and apply it to what you already know. You know how to do this end 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?

(01:02:06): 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. So I want to reframe to the experiences that you already know and that will develop confidence.

Lenny Rachitsky (01:02:20): I like this framing you’re referencing here for product people of this idea. You’re basically trying to position yourself the way you 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 use 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.

Jacob Warwick (01:02:51): The part I don’t want to gloss over is making it frictionless. So interviewing is a skill on both sides. Most people don’t know how to interview very well. It’s tell me about yourself. Tell me about this product you built. Tell me about that, how that looked. You don’t get anywhere talking about the past. 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.”

(01:03:15): Now you’re going to go onto the next person. They’re going to do the same crap. Same thing, same thing, same thing. So you repeat your story, ad nauseum, 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?”

(01:03:42): 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. 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.

(01:04:08): Then even in the interview processes, I might say, “Hey, Lenny. I suspect the next person I talk to from your ecosystem is Marc Andreessen. 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. 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.”

(01:04:37): Then when I talk to Marc, I get to say, “Lenny shared that I should talk about X, Y, and 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 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. What would you like me to say to them? What’s the message you want me to share?”

(01:05:15): And they may not have had them in the interview process in the cycle, but I’m putting them in the cycle. 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.

(01:05:41): 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 coach you 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.

(01:06:11): If you come to me sooner, I might’ve elevated that initial offer 40 without you knowing it and then we moved it even further. So it’s a big process that we need to be mindful of.

Lenny Rachitsky (01:06:21): 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 flip these conversations or take a big chunk of that talk from them asking you 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 it takes track to build this case later.

Jacob Warwick (01:06:53): One of the things I found frustrated 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 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.

(01:07:19): 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 or completely… I’m not saying do this devoid of context. You don’t just blow out and like talk over somebody and ramble, right?

(01:07:40): Which I’m one to talk apparently. But you go into this conversation and you ebb and flow with them, right? But the reason I want you to take ownership is because 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, “Lenny, I saw that that maybe wasn’t the right thing to say. Can you tell me more about that?”

(01:08:19): 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 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?”

(01:08:53): 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 it. Look, we want to know. Maybe we call about a couple of friends that are a similar level. Then you can use objective criteria against them. You’re like, “You mentioned that you valued ICs as much as leaders. I just got curious so I did a little digging and it looks like this is like about 30% under what a leader would make. Is that normal? I appreciate you being an advocate for me and pushing back. Can you help me understand if we could lift this to be more equitable?”

(01:09:36): I’m using information I gathered for them and I’m not just beating them up with it. I’m just saying, “You said we treat this fairly. Prove it or prove to me that you lied.”

Lenny Rachitsky (01:09:47): And this works is what you’re saying because if I was the hiring manager, be like, “No, I’m sorry. That’s just not how it is.”

Jacob Warwick (01:09:53): I mean, in many cases it can be, but I’m trying to open up an emotional conversation more so than logic and credibility because you lose. You’ll always lose the logical incredible 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. 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.

(01:10:25): 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. They draw a card at random, three people, two people, whatever. They get their card and they know they’re werewolves.

(01:10:44): 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.” “Okay, we’re werewolves.” Then they go round by round and they politic to vote somebody off of the table. Only two, three people understand. When the werewolves reach parity with the villagers, the werewolves win. 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 an outnumbered situation.

(01:11:23): 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 the 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.

(01:11:42): So if you are hiring manager, Lenny, and you put your director hat on, it’s easy to deny somebody like that because it’s a little bit easier to find another product manager a little bit. 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?”

Lenny Rachitsky (01:12:18): Let’s try to summarize maybe the top five tactical tips that you’ve shared. If we’re just to go through in bullet points, just things people should keep in mind when they’re trying to negotiate. One that comes to mind is don’t share the number first. Try to get them to share a number first. Is that right?

Jacob Warwick (01:12:35): Yeah. You also have to know how to respond if they share the number first. I’d rather know numbers be discussed if you’re open to just waiting it out and seeing. So important pieces. So the first one is you’d never be so sure of your worth that you wouldn’t accept more. I think Chris Voss quotes that quite frequent. The other one is never split the difference. And I have a good story about that. So just because somebody says, “You started 100, you say 200, they come in at 150, that’s lazy.”

(01:13:09): 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 six months on target earnings. It was all agreed. The paperwork comes back and it says six months base salary, not on target earnings. So that means six months of base salary is like 187.5. So cut his severance in half by doing that.

(01:13:47): Now, his response was, “I’ll just tell the CEO. Let’s up that 90 and it’ll be down 90.” He was going to split the difference of like 260 or something like that, whatever they mass out to. And I said, “Instead, simply ask, was that a mistake?” We had discussed on target earnings that was intentional. Was that a mistake? And he said, “Oh, yeah, it 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.

(01:14:14): And then turns out 12 months later he got fired and then he was able to recoup $350,000 over six months. So little things like trying to split the difference too early can be painful. So that was two points, I think. This is parts I’m bad at, trying to get a list of five.

Lenny Rachitsky (01:14:30): This is great.

Jacob Warwick (01:14:31): Patience is more important. 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. That’s important. I am a big believer in Aristotle and his principles of rhetoric in 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 trained to do that. We don’t show emotion. We don’t show the authentic side of ourselves in corporate. I think oftentimes because we’re working soulless jobs that we don’t believe in and we’re just trying to make do and survive for our families.

(01:15:19): 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 tactical empathy, right? Which that sounds more Machiavellian than anything I’ve ever said. But understanding those motivations and understanding how to play on that can be important. So when we talk about giving people a positive reputation, we’re playing into some emotions here.

(01:15:48): So if I’m a female negotiating with another female, I might say, “I appreciate that you’ve always been an advocate for women and you support one another. That’s something I respect about you.” 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… Go backwards five years in your career. That’s where I’m at right now. If you were in my shoes, what would you ask for?”

(01:16:15): I love that when negotiations stall also, right? “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… This is why it’s also could be difficult in a Zoom. You and I are face to face. We have this problem between us, right? That’s an adversarial position.

(01:16:49): I want you to physically pretend that you’re in the same room and I walked 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 in that. 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.

(01:17:16): Another one is make it about we, not about me. So another severance conversation with a chief marketing officer, this is a $200 million private company a couple years ago. So she comes in, she gets offered $340,000 base salary, 30% bonus, equity. 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 team.

(01:17:51): Now, she was getting pulled from a hot company, which is risky because 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. And so we asked, standards 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.”

(01:18:20): We said, “Well, given that we’ve had a problem with talent being poached and going elsewhere and we just did a big riff, 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 is like, “That’s the woman that negotiated us all severance protections.”

(01:18:50): So we made the company, we used the company’s equitable policies to do that. Now, I will say that’s not common. So if folks are like, “Bam, that’s fantastical. That may not happen.” Especially with private equity, it usually doesn’t. There are ways that we want to appeal to a humanity more so if we can. Bonus point. I know I’m monologuing a lot. Don’t be afraid to get creative. Creativity is interesting. And one time we got someone at G-Wagon after being maxed out on comp. I like this story because it’s so out of this world that you’re not going to get a G-Wagon.

(01:19:27): I promise you, it is likely not going to happen. But we had this CEO who had two offers that were both 2.4 million and they were stalled. First world problem, right? Tiny violin, 2.4 million a year, the CEO deal. And she told me, and this was just a joke. 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. They’re both fine, whatever. And I said, “Well, I don’t know. What kind of car do you like?” And she said, “Oh, I love Mercedes.” And I was like, “Tell them that,” jokingly, because they inevitably came to, “Look, what’s it going to take to hire you?”

(01:20:10): And she’s like, “I don’t know. 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, a G-Wagon.” What happened was all the budgets were capped, but it was a company write-off to have a 6,000-pound vehicle. So it was a $350,000 car added to her contract that was a company write-off that reduced the tax expense. So 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.

Lenny Rachitsky (01:20:48): I love these stories. Another tip you shared just I want to double down on is don’t negotiate over email, make it in person if possible or video call, right?

Jacob Warwick (01:20:58): Yeah, absolutely. Just 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. 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. You can’t control whether someone is 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.

(01:21:26): 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 so that we can get the most out of our time together?” That is a blessing. You couldn’t do that over email.

Lenny Rachitsky (01:21:46): Say things actually do fall apart, say you just pushed too hard and they’re just like, “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?

Jacob Warwick (01:22:02): Couple elements of that story. One, the not delivering pieces, that’s more common. Rescinded offers, I’ve never had a client with a rescinded offer. What I will get is a, “No, this is a top take it or leave it.” Fine. They get an ultimatum. Fine. I have however helped somebody, they weren’t a client, 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.”

(01:22:40): And she was in tears. She lost this deal. Turns out she had a career coach that said, “You need to negotiate like a white man.” That was her advice. “You need to be aggressive, you need to do this, you need to do that. You need to negotiate for your worth.” Which I understand the appeal of that as if I would understand a woman that wants to negotiate like a man and get hers, I respect that. In this situation, the context that was missing is that she was negotiating with other women.

(01:23:08): So she was negotiating with this female CEO and 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. 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.” And I commended her for that. And so what we did was I said, “Look, call the CEO, explain what happened. Share that, obviously, it’s important that women take care of each other. And it’s clear to me that you have. There’s that positive reputation. I got to be honest with you, I hired a coach to try to understand what to do because in the past I’ve 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.”

(01:24:08): Boom, shared identity. They all know. All women know this together collectively. This is a shared identity tribe thing. “I made a mistake and I disagreed with the advice, but I did it anyway because I had to try.” And they brought the offer back on the table for her authenticity and transparency. So that was the path that we… There 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. So when things go south, approach it with honesty, integrity. Say like, “I made a mistake.”

(01:24:41): 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.

Lenny Rachitsky (01:24:57): I love that approach of just like, “Okay, I hired this coach. They gave me bad advice.” Was it actually-

Jacob Warwick (01:25:02): It made me feel good too. I was like, “Should have hired me.”

Lenny Rachitsky (01:25:06): 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, “You should approach it this way,” or it depends on the person.

Jacob Warwick (01:25:18): I take a different approach on every person. 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 or everybody is different culturally. So male, female, every little nuance is important. If you’re gay or you’re black, or there are different challenges that everybody has to overcome. And I remember this was a powerful one. I was speaking to chief. There was about 400 women in chief and I’m the white dude mansplaining to all these women about negotiations. It’s like the scariest position for me to be in.

(01:25:59): 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?” That’s defeatist. That sucks to have that feeling. Now, I don’t know what that feels like. I’ve done fairly well for myself and there’s some advantages that I had, but I said, “Look, how many of you in here are mothers?” Many of these women raise their hands. “How many of you are mothers to daughters?” Many of them raise 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.’”

(01:26:39): And it shocked the room a little because I can’t compete on that level. 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. Here’s the founders coming in again like, “Jacob, don’t tell them to do that.” I don’t want a revolt. Take care of them. Right?

Jacob Warwick (01:27:00): Don’t tell them to do that. I don’t want to revolt, right. Take care of them. Push back because a rising tide raises all ships. 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-

Lenny Rachitsky (01:27:26): [inaudible 01:27:26]-

Jacob Warwick (01:27:25): … a lot of money on this deal.

Lenny Rachitsky (01:27:27): And they came to you to work with you. Oh, I love this.

Jacob Warwick (01:27:29): 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. He had a great relationship with the CEO, 10-year relationship. But the CEO wouldn’t take any action to support him until we made it about we. The CEO had made comments that, “I’m probably going to get fired too.”

(01:27:57): 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.” So then they were full on. You had the CEO and the CPO putting together a game plan to advocate against the private equity to support that transition plan. We got a retention bonus and a severance bonus on the table because of that. Because now the CEO is protected as well, can point back to some precedent. So, not everybody does it out of the goodness of their heart, not in a capitalist society.

(01:28:30): You have to show them your motivations here are important. So, women negotiating, if you want women after you to have an opportunity, have 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. Let’s all push for those to help it make it easier for everyone.

Lenny Rachitsky (01:28:56): I love this point you made about how there’s no one way to approach this. The way I was originally thinking we do this chat is like a step-by-step guide to negotiating. “Here’s what you do with one, two, three, four, and this is how your comp goes way up.”

(01:29:10): And what you told me is that just doesn’t exist. There’s so many variables, there’s so many types of companies, role, seniority, people’s backgrounds. Maybe speak to just like if you ever see someone telling you, “Here’s your steps to negotiate comp,” just it’s probably not real.

Jacob Warwick (01:29:25): 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, you have, 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.

(01:29:54): You’re like, “I don’t have a gun to my head. I just am dealing with my boss, and I want to understand how to do this.” Or you read Getting to Yes, and it’s like, “Well, 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 tip?” Those things are all very true, but it comes off intimidating.

(01:30:20): And when we try to focus so much on frameworks and academic, we stop listening. And that’s one of the most important parts, is curiosity and empathy are the two things you need to have the most. 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. You don’t necessarily know. It’s that information imbalance that you have. And really, what negotiation comes down to information and timing.

(01:30:51): That’s what creates power. 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. So I don’t want it to be overly complicated. One of the… I guess I have to say it. So I’m trying to write a book this year. I’m going to write it. I’m going to write it.

Lenny Rachitsky (01:31:15): Now it must happen. It’s on the record.

Jacob Warwick (01:31:18): Now it must happen. I know. I just kind of clenched up a little bit because I got to do it.

Lenny Rachitsky (01:31:21): It’s still early in the year. You got so much time.

Jacob Warwick (01:31:24): Oh yeah, thanks. I’m a prolific writer. I’ll get after that. But the book title is called Predetermined. And I want it to be Predetermined with a question mark because none of these outcomes are predetermined. No matter what situation you are in your life, how you are raised, it can 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.

(01:31:57): And one of my favorite things to ask somebody, and they’re like, “Oh, Jacob, I want to do this in five years.” I say, “What would that look like if it was done in one? What must be true?” And 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 in the bank, and they’ll be in their late 50s, and they’re like, “Oh, I need 10 to 15 more to retire.” “What? What do you mean you need 10 to 15?”

(01:32:24): I’m like, “If I had a million dollars, I would retire. Give me a break. That seems like so much money to me. Why is that the case?” So I like to challenge those notions there. It’s an important thing to think about. It’s not as step-by-step as it needs to be because 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-

Lenny Rachitsky (01:32:58): Oh, wow.

Jacob Warwick (01:32:58): … big franchise.

Lenny Rachitsky (01:32:59): Cool.

Jacob Warwick (01:32:59): 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 directions going. They’re not writing me right. Fire them.” Offended the original director because they wrote the first two movies, and they were very successful to build this franchise. So pissed off. Next writer comes in. “This is worse than the one before. Can we just hire back the first one and get work through it?”

(01:33:37): So, six 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 to get him to say yes. Here’s a million more dollars.” Didn’t do it. 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. My suggestion was, “Can you ask the actor, this A-list celebrity, to humble themselves and apologize?”

(01:34:15): 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, that’s going to have big impact.” At the end of the day, if you’re making $18 an hour and you negotiate to 24, that’s such a material difference in your life.

(01:34:40): That is so magical to maybe be able to afford gas for the first time. And then I’m telling stories where people haven’t thought about how much gas costs ever. So there are situations. I remember that. Just 10 years ago, well, 12 years ago, I was homeless, 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.

Lenny Rachitsky (01:35:08): 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?

Jacob Warwick (01:35:25): I think what’s interesting about Hollywood is that it’s so far-fetched in… You were talking about what happens when offers get rescinded, right. And before I was working in Hollywood, I would try to talk people into asking for $20,000 more, which, after taxes, is like eight. And then when you look at it’s like $400 a month or whatever. You’re struggling to maybe ask for 10, 20 grand. In Hollywood, we did this deal with, I can’t share who, A-list celebrity.

(01:35:59): And the company said, “We want to pay her $5 million for this movie. “And the attorney came back, “We want $22 million.” Talk about being aggressive. And the production company’s like, “All right, how about 13?” And this was in a two-day span. So, they went from five million to $13 million in two days. And the other, they’re like, “Well, instead of 22, how about 18?” They’re moving $4 million chunks at a time, and we’re over here in tech going like, “Oh, I wonder if I can get 10,000.”

(01:36:37): So that’s something that I just find absolutely wild. The bigger the… This is just like you want to make money, solve rich people problems. That’s what happens. It’s just escalated. I can only imagine what a negotiation with Elon Musk would be like. “Throw 100 billion at it.” And you’re like, “Oh my gosh.” I also found out that a million seconds is like 11 days. Have you ever heard this? A million seconds-

Lenny Rachitsky (01:37:04): Mm-mm.

Jacob Warwick (01:37:04): … is 11 days. Do you know how long a billion seconds is?

Lenny Rachitsky (01:37:08): Probably hundreds of years.

Jacob Warwick (01:37:11): It’s like 30.

Lenny Rachitsky (01:37:12): 30 years.

Jacob Warwick (01:37:14): It’s 31 years. So, between 11 days, that’s the discrepancy between a million and a billion.

Lenny Rachitsky (01:37:17): Oh.

Jacob Warwick (01:37:18): And so these are just… 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. You have to start networking and making connections with folks that can do that with you.

Lenny Rachitsky (01:37:36): 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?

Jacob Warwick (01:37:53): You always give me these nuanced [inaudible 01:37:56]. So it’s they get it from either recruiter or they get it from-

Lenny Rachitsky (01:38:00): Yeah, let’s say the recruiters. This is probably a [inaudible 01:38:02]-

Jacob Warwick (01:38:02): … [inaudible 01:38:02].

Lenny Rachitsky (01:38:02): Yeah.

Jacob Warwick (01:38:03): Recruiters going to… again, they’re probably going to have that 20%. We have a room there. If you’re okay with that, I might, again, just say, “What’s the chance we can bump that? This is what I was looking for.” 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 tried to be reasonable.

(01:38:37): So it’s like, “Look, I was hoping for 150,000 more.” Sometimes you get 70. Sometimes you get 50. But if you ask for 50 more, you would’ve got 15. 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. 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?”

(01:39:09): 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 and 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.”

(01:39:41): That will not work. And I’ve noticed this in our back and forth in your emails. You’ll respond with two words. That’s all you need. You don’t often need more. So, 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.

(01:40:09): If it’s not, I do have… 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 Lenny’s videos. 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 it’s not like you’re… If you need the actual specifics, there are a lot of scenarios I’ve already kind of covered [inaudible 01:40:29]-

Lenny Rachitsky (01:40:29): Amazing. And we’ll link to all that. And I think it’s… 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. This is… 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’re trying to… It’s not like some deal [inaudible 01:40:50] here.

Jacob Warwick (01:40:51): My mission is to make what I’ve learned from very successful people more accessible. And if you put a pay band on all of that, you’re not making it accessible. And my hourly fees are very high. So it’s like I don’t want to push for that and feel like I’m unabtainable. So I want to give away as much as I can. And it’s these things shouldn’t be gatekept. They often are. But yeah, I was mentioned a little bit in the green room.

(01:41:19): I felt a little powerless growing up. It 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. So it’s just money. Money is like, “I’m not going to get hit. Nobody’s going to get hurt here.”

(01:41:50): 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, because I could see their growth, and that’s what became most fulfilling.

Lenny Rachitsky (01:42:17): There’s a whole other conversation we could have about that whole part of your journey.

Jacob Warwick (01:42:21): We got to be careful about that one. Yeah.

Lenny Rachitsky (01:42:23): All right.

Jacob Warwick (01:42:24): That one, I might start crying on that one.

Lenny Rachitsky (01:42:26): Okay. Well, that makes good content. That could be part two. Jacob, you’re-

Jacob Warwick (01:42:31): That’d be the comments. Like, “Next time, make Jacob cry, Lenny. Go for the kill. Go for the kill.”

Lenny Rachitsky (01:42:37): 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?

Jacob Warwick (01:42:49): 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, or a lot of these people are parents, and you want to be the best version of yourself and show to your kids that you could survive anything. You’re going to get a couple of bruises along the way. These are great first-world problems to try to fight for. It’s not going to take away your home. The thing is, you’re only going to make life better around you. If your cup overfloweth, you’ll be able to give more to others.

(01:43:23): So it’s not about, “Am I worth it? Is that…” It’s like, if you are a generous person naturally, you can be more generous if you have more wealth. If you’re afraid of wealth, this is something that really screwed me up. I used to despise wealth. I despised it. 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. 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.

(01:44:01): 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, 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 a 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.

Lenny Rachitsky (01:44:25): That is beautiful. I’m also realizing as we’re talking, we haven’t mentioned AI once at this conversation [inaudible 01:44:32]-

Jacob Warwick (01:44:31): No, no.

Lenny Rachitsky (01:44:32): Which is incredible.

Jacob Warwick (01:44:34): [inaudible 01:44:34].

Lenny Rachitsky (01:44:34): I love that.

Jacob Warwick (01:44:34): No, no. The listeners are like, “Oh, thank goodness.”

Lenny Rachitsky (01:44:34): Yeah, that’s how I feel.

Jacob Warwick (01:44:36): Right. Thank goodness.

Lenny Rachitsky (01:44:39): Just once in a while [inaudible 01:44:41]-

Jacob Warwick (01:44:41): It’s because I don’t want AI to replace me, Lenny. I don’t want it.

Lenny Rachitsky (01:44:46): Yeah. I don’t even know. Anyway, we’re getting to it. Okay. Well…

Jacob Warwick (01:44:51): Good. I got you speechless. That’s the job. If you get the podcast host speechless, you’re doing your job. That’s great.

Lenny Rachitsky (01:44:56): 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?

Jacob Warwick (01:45:03): All right. I’ll do the best I can. Yeah.

Lenny Rachitsky (01:45:06): Here we go. What are two or three books you find yourself recommending most to other people?

Jacob Warwick (01:45:12): Influence by Robert Cialdini.

Lenny Rachitsky (01:45:16): It’s weird. [inaudible 01:45:17]-

Jacob Warwick (01:45:17): [inaudible 01:45:17].

Lenny Rachitsky (01:45:17): That’s the one.

Jacob Warwick (01:45:18): That’s the one. I mean, I like Herb Cohen’s You Can Negotiate Anything. It’s a little dated. 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 negotiating dishwashers and stuff, not going to market with Meta versus Instagram and the acquisition. It’s not complicated. It’s like, here’s an apple, and here’s an orange, and here’s the concept in negotiation really spelled out simple.

(01:45:46): 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’m like, I wanted to write a book a couple of years ago, and then I read his and said, “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.

(01:46:11): It really breaks it down in an easy way. And that could be 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. 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.

Lenny Rachitsky (01:46:36): I think Radical Candor is the second most mentioned book on this podcast, behind High Output Management.

Jacob Warwick (01:46:41): Yeah, I have not read that.

Lenny Rachitsky (01:46:43): Yeah, I don’t think-

Jacob Warwick (01:46:44): Admittedly, I’m bad at-

Lenny Rachitsky (01:46:48): … I don’t think you need to.

Jacob Warwick (01:46:48): … consuming content. I’m not… I only create. I’ve got this rule that 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.

Lenny Rachitsky (01:46:59): That’s a great framework. Okay. Next question. Do you have a favorite recent movie or TV show you’ve really enjoyed?

Jacob Warwick (01:47:04): I’ve been really liking watching Luca, the Disney movie. Having a toddler and a newborn, I really just watch cartoons now. So, 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.

Lenny Rachitsky (01:47:33): Sounds not appealing, but…

Jacob Warwick (01:47:37): 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.”

Lenny Rachitsky (01:47:48): Okay.

Jacob Warwick (01:47:49): Finding a little boredom and creativity, that’s how you get creative. If you’re constantly, if it’s like Cocoa Melon and Paw Patrol, and you’re like, you can hear the beats in your head, you can’t do that. I not going to… I can’t do that to my kids.

Lenny Rachitsky (01:48:03): Favorite recent product you’ve discovered that you love?

Jacob Warwick (01:48:06): Claude Cowork. I mean, I-

Lenny Rachitsky (01:48:10): Good one.

Jacob Warwick (01:48:10): … I love Claude Cowork. Sorry for mentioning AI, but I really only use a handful of products. So, Claude Coworker is one of them, and MacroFactor for macro tracking. And I got a WHOOP this last year, and I’ve lost almost 50 pounds just paying attention to my WHOOP stats and trying to sleep.

(01:48:30): And 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.

Lenny Rachitsky (01:48:44): Do you have a favorite life motto that you find yourself coming back to in work or in life?

Jacob Warwick (01:48:48): Always give more than you expect to receive.

Lenny Rachitsky (01:48:51): It’s like a golden rule, plus plus.

Jacob Warwick (01:48:54): 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. And how to win friends and influence people, right. That’s not why I do it. I’m just suggesting that’s an-

Lenny Rachitsky (01:49:15): [inaudible 01:49:15]-

Jacob Warwick (01:49:14): … area where you can read more on that.

Lenny Rachitsky (01:49:17): Final question, you’re starting a foundation, a nonprofit.

Jacob Warwick (01:49:22): Yeah. I’m working for, or I’m on the board of the Cody Dieruff Foundation, and that’s in Bozeman, Montana. And what we do is my son has cystic fibrosis, and cystic fibrosis is a genetic condition. I’ll actually talk a little bit more about it in Predetermined because his life was, quote, unquote, predetermined. We’re not really accepting that. But with our foundation, we help rural parts of Montana get access to the healthcare that they need. And so they got me with this. So we helped this family.

(01:49:58): 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. Life expectancy used to be seven 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 so her 27-year-old son, two years younger, needed a lung transplant, and she actually found out that our agency existed in that period.

(01:50:32): And we funded the life flight to Denver Children’s Hospital to get that lifesaving surgery and saved her son’s life. And that sounds like a great story. The part that got me was that now the mama feels all this guilt because she could have saved her son’s life if she knew we existed. And that part, I was in tears thinking about that. I did… I’ve 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.

(01:51:10): I did all this networking to be selfish and build my career and do these things. And 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 at Denver Children’s Hospital at Stanford. I got a call from the FDA that said, “Don’t worry, the son… your son’s medication is getting lower 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.”

(01:51:41): So I felt this is immense blessing and support through that. So that’s that foundation. We support these rural areas that don’t have access to that healthcare. And then I’ve also started conversations with the Cystic Fibrosis Foundation, which really helped funding… They help fund the lifesaving medication that changes the life expectancy from seven to 70 years old. They are expected to have full lives now. So, that’s something that I’m very passionate about.

Lenny Rachitsky (01:52:07): Incredible. Oh, man. There’s so many topics and directions we could have gone with this. Jacob-

Jacob Warwick (01:52:15): I know I blew you out. I blew you out of the water, man. Sorry. I monologue like nobody’s business.

Lenny Rachitsky (01:52:22): There’s this… 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?

Jacob Warwick (01:52:34): 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 in 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 eight hours that I filmed. I used to sell it for like a grand, and now I just give it away for free.

(01:53:21): That’s also available on the YouTube, which is Execs and the City, which I have like a hundred 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 JacobGPT. Well, it’s another AI mentioned that’s digitally trained on… I think you have one too, right?

Lenny Rachitsky (01:53:43): Yep.

Jacob Warwick (01:53:43): Was like trained-

Lenny Rachitsky (01:53:44): Lennybot.com.

Jacob Warwick (01:53:44): … on all my content. Lenny Bot. Yeah. So it’s like a Jacob Bot, which is a minor Lenny Bot trained on my content. 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.

Lenny Rachitsky (01:54:10): Jacob, this was awesome. Thank you so much for being here.

Jacob Warwick (01:54:13): 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.

Lenny Rachitsky (01:54:20): 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 to show all the guests that our goal is to have fun. So [inaudible 01:54:27]. All right, Jacob, thank you so much. Bye everyone. Thank you so much for listening.

(01:54:32): 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.