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

23:03Lenny Rachitsky:more likely to get your way. Talk us through this, the kind of the process you would recommend from, I get an offer, recruiter sends me, here's your offer, 300K salary, some kind of equity. What's kind of like the step-by-step you, and I know this is depends on the role, seniority, type of company, PE, VC-backed startup, because it's very scary to push back and be like, oh, I want more. What's like that first email slash reply to that email look like typically? Like, 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?

23:41Lenny Rachitsky:Because that feels so scary. 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 is going to get done, even if you're on the fence about it. right now it's not to say you're so excited that it's a sure thing and you're not showing that you're disappointed even if you are right so i'm grateful i'm looking forward to working with you i want to review this over the next couple of days right i'll talk to my wife about it you'll 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 like you may have five or six people see that right employment lawyer all that that stuff is expected right so you're going through the process.

24:29I'm going to take a couple of days to process this. I'll get back to you. I may have a couple of questions, right? But we'll loop back and it shouldn't be a problem. I imagine we start working together in a couple of weeks, right? So the point is you have to sell that the deal is going to be done, which helps them feel like it's going to move forward regardless, right? So any ask that you make is not going to be egregious. Now, oftentimes the higher you anchor, the better you're going to perform, which can be frustrating because you don't necessarily want to be like, oh, I increased it 40 % or anything like that.

25:03Now, this is where a lot of nuance comes in. So 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?

25:35Right? Or they may say, we've comped you in the middle part of the range, right? You might say, what does the top end look like? You know, what must I do to fit those needs for you? Can you help me understand? Now, for a lot of folks, especially in this market, if we talk about what it was like in 2021 versus what it's like now, Now, there's some over-leveling that's happened. So 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, you know, as we had this conversation, I'm likely a little more horsepower than you anticipated, right?

26:13What's the chance we can come in and restructure the comp for the type of talent we're bringing in? And so 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.

26:52I can see why some listeners are like, well, I'm not there in my career yet. In that case, this is just how it gets done. This is how bigger moves happen. It doesn't mean you can't push for maybe 20 % more naturally. Nat, 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, right?

27:34But 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.

27:39Lenny Rachitsky:I love that phrase you just shared of what's the chance there's a bit more here? as expecting number X? Is that the phrase you recommend, that approach of just a soft pushback just to see? Sometimes. Again, it really depends on the leveling. If you're very senior, I typically don't want to re-anchor with a number because you should ever be so sure of what you're worth that you wouldn't accept more. Right? And when you anchor, that's the ceiling. And what often happens is naturally they want to split the difference. and so i'll have a quick there's a quick hollywood story here so we had a writer who had a seven hundred thousand dollar contract right so seven hundred and the agent that i was working with was was saying like this uh this writer has the most aggressive attorneys in la right they're super aggressive uh and i said well how do you know first of all well if that's what they're perceived does.

28:39So the production studio offers this writer 700. The attorneys come back and say, we want 1.3, right? 1.3 million. And the studio said, fine, we'll do a million. And they settled at a million. And I find that really interesting because the studio came up 300 ,000 and the attorneys lost 300 ,000. So they 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? 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.

29:23So 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. So those are things that you've got to slow down to really understand where is the value being made here. In that movie, that movie could make$50 million. Do you think$1 million for writing was worth it for someone who controlled the creative there? I don't know. A 50 to 1 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.

29:58This is how Tom Brady had his contract at Tampa Bay. Win 8 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 uh get this get to the super bowl x win super bowl mvp two and a half million more like so performance

30:17Lenny Rachitsky:based triggers i love just how how much you love this it's just clear this is so interesting it's really nerdy i know like i like obsess over it in a weird way but uh i don't know it's uh it's been kind of baked into my my psyche for a long time probably because i felt so powerless growing up that I'm so interested in how, 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 like off to the races. So that's been helpful. Uh, on that note, uh, do these tactics work on, on kids and wives?

30:55Lenny Rachitsky:Is this something that translates? 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 what's don't don't pull that on me i know what you're doing right and toddlers are terrorists so i don't i haven't figured that one out i i've resort to bribes and maybe that is a little machiavellian on the on the toddlers you can be you can be out of your mind working on that but yeah don't recommend it with your spouse i would pay a lot of money for a version of you for toddlers oh my god it's like i try to negotiate with a kid i'm like i'm like three minutes he's like six i'm like four minutes no six he never budges five minutes he's like eight although sometimes does that too yeah i go do you do you want a binky and he goes five binkies i go i don't know if we have five and he's all ten binkies like whatever you need i'll get it You go to sleep.

31:54Yeah. Yeah. Please sleep.

31:56Lenny Rachitsky:Yeah. Yeah. We need, we need this for toddlers. I would, I would, I would subscribe. Miss Rachel's the closest thing we got. Yeah. Okay. So coming back to this conversation 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? Yeah, there's, 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.

32:36That can be okay. There's nothing wrong with sharing your number and getting a deal that moves the needle early in your career or 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. right so things start changing as you mature in your career and so when you're working with a top recruiter they don't ask you about con 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 like it's very difficult to optimize for inbound attention the higher up you go unless you become very popular right and then what happens is you share less information because people come to you in a Nine times out of 10, a recruiter reaching out to you is going to ask that number, right?

33:27One time out of 10, they're going to just focus on the value creation. Those are the ones you want to focus on the best possible. But it could be confusing because so often you get a different side of the story, more of the commodity type stuff. So typically I'd recommend you answer, 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.

34:03I just need to know a number, right? Now, I mean, this is what, 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. like so be it right so culturally there's a lot of differences in how this conversation happened and so they say look we we need a number from you you might say look i'm uncomfortable doing that right now because i don't understand the scope of the role can you help me understand what you had in mind right the reason i learned this is i used to be a marketing manager making twelve dollars an hour in downtown san francisco for series a companies not knowing that twelve dollars an hour wasn't a lot of money.

34:44I just didn't know any better. But then I left out marketing managers and I saw that they made 60 grand a year and I was suddenly got offended at how little money I was making. Right. Then I got promoted to director in that period and was making $14 an hour. Good for me. Right. And then I saw that marketing directors were making 110 ,000 at the time. So when a recruiter called me, I pulled that. I didn't want to tell him I was making$14 an hour. They'd be like, who is this kid? He's not very good. That's fake title. And instead I said, what did you have in mind? And they said, oh, we're looking at 110 to 130.

35:13And I'd say, oh, I'm on the upper end of that now. And so I went from$14 an hour to$120 ,000 a year in a single month, a single jump, just like that. That changed my life. One negotiator. So one of the reasons I'm so passionate about that. I hated the marketing work for what it's worth, but I thought like 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 do things in your experience ever fall apart

35:40Lenny Rachitsky: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 gonna hate me and they're gonna be like well it's not worth it we're gonna move on has that ever happened what are the odds that might happen a couple things about power right so if you have the ability to say no you have infinite power right the nuance changes when when you don't have a job and you need to pay your mortgage you might answer that differently because you want something right now this isn't to shame somebody who's feeling that way right if you're out of work for six weeks in san francisco you're homeless right 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 right but understand that once you're employed and somebody's asking you When your needs are already getting met, why do you need to get pushed around?

36:33This 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 confident. When you're out of work and you have the uncomfort of being out of work 6 months, 12 months, 18 months, you have an identity tied to a chief product officer role or a VP of product. Like 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.

37:07And we want that pain to end. And 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. 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 right now again i might accept that because i need the money i understand right but it's very telling how somebody's going to treat you depending on very simple pushbacks and one behavioral psychology hack here is we give someone a positive reputation that they want to withhold, whether they deserve it or not.

37:58So in this instance, you'd say the recruiter, I want to thank you for being an advocate for me and for respecting that I won't share compensation figures right. I appreciate that. And then they are trapped. They have to say, no, I don't respect you. I have to do this. Or they have to say, you're right like that makes sense let me move you forward or not right another option you don't necessarily know if you're the best solution for that fit or not and so we're obviously very ingrained when a recruiter reaches out to you and they say look we're going to pay 120 and you make 150 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 you can always say no later right just because having that practice is going to make you hundreds of thousands, if not millions more in your career.

38:51Alternatively, 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, in usage, it gave us a senior PM role. And what you realized is the JD and all of the work that you did is actually a director role, but they're not going to pay for a director role. How often does that happen? You get to say, look, this role isn't in alignment with where we're headed, right? 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.

39:28We're going to extend for you. Like my first VP role came out of turning down a content manager position for 70 ,000. And six months later, I landed a VP for a quarter million. Like that was my, my first realm into VP. The initial offer was for content. So it came three, four levels up the food chain. That was a long negotiation, but these things can happen if you don't say no too quickly.

39:53Lenny Rachitsky: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. 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, right, which I'll occasionally do with some communities, I'll ask them who is actually doing the job that's on their job description.

40:35Nobody will raise their hand. It's not like you have your job description right there and that's what you do. Right. There's always so much more that's not documented. Right. Now, when you're going into a position, you see a JD, you're like, yeah, I could do all those things. But there's so much more. Right. This is another reason that anchoring to a number too early is tough because you anchor to, oh, this is, this is fair for a senior PM role. Right. This is fair. Then you go through the process of the interviewing. It's very clear that it's a director poll. You're going to leave five people.

41:07They scoop another team under you. oh we're going to put a product-led growth motion under you too there's a whole engineering pod and there's this and there's this all of a sudden that's called scope creep right so they scope creep the role they talk about how they want a senior hire they're excited about you they get you excited about it and then 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.

41:38And so that's why we don't want to anchor too early. We want to understand. And so this is one thing I wish, especially product engineers, designers, that side of the product stack, I would love for you to treat more of these like a sales conversation, right? You are an enterprise solution, a consulting solution that is several hundred thousand dollars, if not millions of dollars a year. If you were to sell that product into an organization, think enterprise B2B deals, and I know I'm getting a little buzzwordy here, big an enterprise B2B deal to Salesforce and you're going to sell a million and a half dollar product.

42:14It would take you 18 months to develop the relationships and close that deal. You have to develop champions in the organization. You have to understand what value you can create for each of those people so that they can advocate for you. You don't come in and pitch them the price right off the bat. You need to understand the value. So through the process, it's a discovery process. Why am I here? What gets you excited about me? Right? That's how we start a conversation. Too many interviews start with, you know, tell me about yourself. Tell me about this stuff in the past. If you're talking about your past, you're on the back foot and you're losing that conversation.

42:53You're the one revealing information. You're not getting anything. We instead want to have a conversation and say, look, some of the best interviews I've always have felt a little bit more like consultations or brainstorming sessions. Are you open to having a chat like that today? That's the first step. Typically they say, yeah, that sounds way better than me trying to drill you with questions. So let me ask you, what are some of the things that you're excited about? I imagine, Lenny, you're excited to talk to me because I can help some of your audience negotiate. You've seen proof where dozens of your subscribers have made more money with the article we wrote together.

43:27You've even seen that some of your guests unknowingly have been negotiated against with some of the work that I've done. Is there anything that I missed? What's exciting to you? So I want to clarify why I'm in the room with you. Right? So we do that as a 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? right? Then they're revealing information. You take control of that conversation.

44:03And then we want to share, what have you done about it? Like how big of a problem is this in the organization? This is basically a SWOT analysis. Like 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? So I want to ask all these discovery questions. They're like, oh, look, it's a$10 million dollar problem or we've 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 right 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 force them to visualize a utopian situation and who was right next to them doing that i was so when it comes to your competition there is no competition i'm the only person who walked you into a vacation that you want to be in, looking forward to your head held high in a board meeting that's usually stressful, but instead this time, because you worked with me, it's not stressful.

45:33Then all of a sudden, when it comes to the offer stage, there may be five other PMs, but I can only imagine working with Jacob. And so when I push back, the likelihood that I break the rules is significantly higher than if I hadn't done that.

45:44Lenny Rachitsky:This is amazing. So trying to just summarize what you're sharing here. And I think it's important for people to also know, like you can do it in your own words this is likely not something you'll just be able to pop out and do like this is something that takes time to do well and it feels awkward probably and that's why people work with you that they're like you probably role play and all these things but still like there's things people can pull out of this that they can do on their own it could be tricky to understand where your value is right because you're so close to it you just do this every day and for you know product folks that only listen to product folks and and are in the product ecosystem in your bubble, Lenny, they're not seeing the impact on marketing.

46:24They'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.

46:44Lenny Rachitsky:I think this is important to just briefly summarize your approach. so the idea here is uh 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 like here's the many problems we can help you with and then help them visualize you described it as sell the vacation help them visualize okay now that this is solved how is how how awesome would that be and part there's like all this psychological stuff you're throwing in there just yeah i can i can really make this concrete with a quick story let's do it so there's a very famous musician who was born the same year as me for those super sleuths out there who had a tour a billion dollar tour in a documentary and the director of said tour was a hot commodity in Hollywood.

47:46Every agency wanted to sign this director. This director didn't want to just do movie documentaries, right? Wanted to start producing actual movies. Like that's the dream, right? So every agency wanted to sign this hot director who just did this billion dollar deal with, people already know who it is, right? And so my client, the agent asked me, like, we got to sign this. Like it would be stupid to go to any other agency, right? We've done this. We've done that. We've represented Julia Roberts and Matt Damon and all this. They're just naming, name dropping, right? Now, this is actually a problem because if we're leaning on logic and credibility, we're losing.

48:26We need to sell the future and own the emotion. And so she just asked me, how do we close this deal? And to me, this was very simple. I said, if you already had the job, who would you introduce him to? If you already had it, the deal's already signed. So put yourself in the position that you're already doing the job. That's why in 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.

48:58Did you see I have, you know, 3 million words written? Like, why wouldn't you want to be the guest? You're like, I don't care about what you've done. I care about what you'll provide my audience, right? So in this deal, we get into the meeting. It's a big day, right? and I said, make the schedule the appointment already. Work with the assistant, schedule the appointment, right? 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? And so my client says, what are you doing on Friday?

49:28I cleared a lunch with your assistant. And he says, well, I guess I'm going to lunch. And she's like, great, I'll have you meet Steven. And he said, Steven who? and she said steven spielberg and then some form after that it was where do i sign because the meeting was already set with steven spielberg for somebody who wants to get into film production what better meeting to have right so for the other agencies they're like we're the greatest thing like 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.

50:08Lenny Rachitsky: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 - 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. And so they might say, oh, I need, you know, 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.

50:43Let me make a text for you real quick. And I'll just do it while I'm on the phone. Just hold on a second. Hold on. And then what happens is they get the beep. That's reciprocity. Like I'm triggering a reciprocity imbalance. And then I'm making another one for them. So I'll sometimes do two or three introductions right then and there. And they see the value before I'm even off the phone. What I've also done is I've given three different touch points where I can make sure that that person is following through. I can get a 360 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.

51:17I'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. And in this instance, like 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, right? What would that mean to you? And also, what did we do to make it so successful? What are the comments that people had to put down below? What are the things they said to make you feel like my conversation with Jacob was the best conversation I had all year?

51:56What would that look like to you?

51:58Lenny Rachitsky:Like, I immediately love this question as a, you know, like it sounds to people like this is manipulative and like 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. I guess to answer your question, I would just love it to be very concrete tactical advice that people can use to help negotiate their comp. And they spread this with all their friends that are like, this is the best thing you've ever heard around comp.

52:28And 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 was an asshole, right? I'm curious. And sometimes I just make a complete reframe. So there's no other option, right? Well, I'm obviously not going to say you're an asshole. So I'm going to say you're the great thing that I want you to say.

53:00I'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 Jew, right? I will say, I hope that you use this for good and not evil, but this is just the way power works, right? I would hope that in the comment section, you say Lenny this was such a refreshing and energetic podcast like this is what we want more of this is exciting we've done a lot of stuff in AI this was very cool and different right so I'm suggesting if you felt that way share something like that below right too many YouTube videos like oh like and subscribe that's all they do right which does trigger action it's a very simple thing.

53:40But 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've not only know about it, but they know what they said about them. Similar to when somebody's like, oh, Lenny, we're going to do reference checks on you. What's the first thing you do? You call all those references and you say, what are you going to say about me? Right? Ideally, you can control that to some capacity and improve the likelihood of you moving forward.

54:13So we already do this. We just have to integrate it into some everyday conversations and you can better control outcomes. It's the same interview process. When you go back to your committee, are you going to say, Jacob solved XYZ and we're excited? Like slam dunk, let's move forward. I like really quick slam dunk, right? Easy to remember. or are you going to say there's a couple of 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 so what are you going to say is this a slam dunk what's one thing I should have asked that I didn't?

55:02What 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 and 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.

55:31Lenny Rachitsky:Now, this is so awesome. So, you know, 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. Like 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 happy. And you better deliver, right? And that's the other thing.

56:04It sounds like if this guy can't deliver, it's not going to happen. Or if this gal can't deliver, that's frustrating, right? I'm not suggesting go so far outside of your comfort zone that you feel like you can't deliver, right? Because that reputation will haunt you, right? You have to really understand. And I would also add that I wouldn't be so sure that I'm going to fix the onboarding flow. I wouldn't be so sure 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 like I just want the pain to be over I'm asking you to slow it down the more you slow down the process the more you fight back about the manufactured urgency of us needing to get into that role sooner the more information you're going to understand about that company and how you could really help, right?

56:54So you could say, you know, Lenny, I hear that you want to fix the onboarding flow. I hear that. I hear this. But it sounds like that product might be deprecated anyway in this wave of AI. Is that a possibility? What I don't want to do is prioritize something that the team's going to cut, right? That's going to hurt the P &L or whatever. Now, I can only ask that question if I've truly asked the right questions to understand, right? So you may come in, this is the same concept as never be so sure of your worth that you wouldn't accept more. You're so sure of the job description that they need these three things that you don't even try to ask the questions to understand what the deeper problem is.

57:31And 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. 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.

58:01Lenny Rachitsky:I like that you went there around don't over-promise because it's easy to say, we're going to solve all your pain. I'm going to be the best thing to have. Under-promise, over-deliver. Always. Under-promise, over-deliver. This episode is brought to you by Omni. Many product teams today are in the process of debating how to ship AI analytics. The hard part is obvious. Having an LLM guest at SQL in production is a huge mess and just a bad idea. Omni takes a different approach. They have a semantic layer built in so that when you embed their analytics, the AI actually knows your business definitions, not just your raw tables.

58:38Lenny Rachitsky:You can test queries, validate the reasoning, and lock down permissions before anything hits production. If you want AI analytics in your product without building the whole stack from scratch, check out omni.co slash Lenny for a free three-week trial. Companies like Perplexity, DBT, and BuzzFeed use Omni to ship analytics their customers can trust. That's O-M-N-I dot C-O slash Lenny. There's this balance of being confident in your abilities to achieve something big and solve problems. and then there's this other piece of just don't over promise is there anything you help people do to help feel more confident about they will actually be a huge asset to this company and they're worth all this extra money how do you is it like a pep talk how do you help people yeah part of my hat is hype man hat right you got to be a hype man to a degree and i work with some of the most privileged and successful people in the world right it's not that hard to say look at your life and look at your choices, most of the things you've done have been good, right?

59:39At least financially, right? We could debate about the ethics of the companies they work for and those things, right? Now, most of the decisions that you've made in your career have made you a top 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 put it, 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. Like if you understand enterprise sales, you understand how to do this. You just don't know how to do it for yourself.

1:00:09If 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 in 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 a term I use a lot, which I know product leaders will use also. We want to eliminate friction, right?

1:00:41How does that look in your job search? Well, what does the customer want? Who's your buyer? The buyer is the hiring manager. Maybe it's the chief product officer. Maybe it's the CEO. What do they care about? When you're doing it for a company, you know which customers to interview. You know how to do that. Well, you need to interview lots of CEOs. You need to interview lots of salespeople who are trying to solve this growth problem or lots of AI side. And again, it's not just product, right? So you're now interviewing your customers. You're understanding their needs. Now you're designing solutions for their needs.

1:01:12Now, how do you make it as frictionless as possible so it's a no-brainer and they go through your user flow as easy as possible? So for product folks, instead of thinking, wow, this stuff sounds like Machiavellian manipulation and it sounds like a power trip and it sounds like something I could never do because I'm not maybe I'm not as gregarious and maybe I'm not a six foot three tall white dude in California who's got the sales persona and he's got that extroversion. I'm not that. 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 in product.

1:01:51Design it for your career. And you remember the early days of writing PRDs and how rough it was? Remember how rough it was to go back to the engineering team and just little by little get product sprints out where the product is just moving a little bit at a time. Remember how hard that was? The early days of managing your career like this will feel like that too. But you also know that if you're 10 years in your career, this stuff becomes second danger, right? So I want to reframe to the experiences that you already know, and that will develop confidence.

1:02:20Lenny Rachitsky:I like this framing you're referencing here for product people of this idea. Like you're basically trying to position yourself the way you 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 in this and you do that by understanding you do user research you understand their pain points you understand how to position it so that you make it clear this will solve your pain point essentially that's what you're describing from when you're interviewing is think about it that same way the part i don't want to gloss over is making it frictionless right so interviewing is a skill on both sides most people don't know how to interview very well it's tell me about yourself like tell me about this product you built tell me about that how that look you don't get anywhere talking about the past like you you might build credibility and all that great you don't start solving problems in that process so they're like okay well i saw that now you're going to go on to the next person they're going to do the same crap right same thing same thing same thing so you repeat your story ad nauseam and you never learn anything and you never grow so how do we make this frictionless well i want to make it cognitively easier for you to have a conversation with me by leading.

1:03:32That's why I had that framework I was talking about earlier. Like, why am I here? What are the problems you have? I suspect it's this. What have you done about it? What would it look like if we solved it? Now, I'm taking so much of the pressure off of you. I'm controlling the narrative and I'm collecting more information while revealing none about my comp expectations. And what I'm focused on is creating as much value as possible. Now, there are situations where companies don't have the budget, right? Like, this isn't a miracle drug kind of thing, but I'm making it frictionless to at least get to the part where they want you.

1:04:03That's the first step. They have to want you for you to have any leverage, right? Then even in the interview processes, I might say, hey, Lenny, you know, I suspect the next person I talk to from your ecosystem is Mark Andreessen, right? Can you give me some advice on how I should work with Mark? I want you to coach me on how to deal with Mark. That's going to make it more frictionless, right? Now, I also want to put you in a position to be a coach because coaches want their players to succeed. So if I'm having you coach me, psychologically, you're going to go talk to Mark and you're going to say, hey, Mark, you're going to have to talk to Jacob for all these reasons, right?

1:04:37Then when I talk to Mark, I get to say, you know, Lenny shared that I should talk about X, Y, and Z thing. Are those, 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, right? What would you like me to say to them?

1:05:13What's the message you want me to share? and they may not have had them in the interview process in the cycle, but I'm putting them in the cycle. Like I'm making it easier for you to know who to introduce me to next. And then I'll even go as far as saying, I'm not available again until Thursday. What's the chance that time works? So I'm building scarcity about my time. I can meet with this VP then, but I'm making myself stickier in the organization. I'm getting more knowledge about what people need, right? So this 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.

1:05:50So you're getting the inside scoop on how to navigate that. That's how you become hyper-valuable. You need to create that leverage if you want to take that standard 20 % we talked about and make it 40 or more. That's why it starts much sooner, because if you're not doing that, if you come to me and you're like, Jacob, I have an offer, I can get you maybe 40. right if you come to me sooner i might have elevated that initial offer 40 without you knowing it and then we moved it even further right so it's a big process that we need to be mindful of

1:06:21Lenny Rachitsky:so it seems like a big part of your process and advice is to flip it flip the interview as much as you can to extract information so that you can build a case of how you will solve their pain say you're like an ic product manager interviewing at meta what are the odds you can kind of flip these conversations or take a big chunk of that talk from them asking you, you know, their standard questions to you asking them what problems, what are the biggest problems? What would be awesome if I came in? Like all that stuff you shared about to extract to build this case later. One of the things I found 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.

1:07:02Now I have seen specifically with meta, I actually interviewed for a meta IC manager role, like an high nine, 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 I-9 level and they were rewarding them very well. I don't think it changes. I think that whether you're a leader of people or you're a leader of process, you're still a leader. And the reason I propose taking ownership of the conversation isn't to be steamrolling or talking over people or, or completely like, I'm not saying do this devoid of context.

1:07:36You don't just blow out and like talk over somebody and ramble, right? 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. I can't. So as a coach, I can't control how they show up, but you can control how you show up. And we can work to navigate. And then you start to get some, I guess, nuanced skills where you read body language and you feel comfortable saying, you know, Lenny, I saw that that maybe wasn't the right thing to say.

1:08:17Can you tell me more about that? Then you start getting confidence. And I say assertiveness, not aggressiveness. There's a difference. And so that comes across as confidence. And so I don't think there's a difference between being an IC and being a leader in terms of how you approach this. But I have noticed a difference in the pay, and that can be frustrating. So that means 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?

1:08:52I 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. We 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 ISEs as much as leaders, right? And I just got curious. So I did a little digging and it looks like this, this is like about 30 % under what a leader would make. Is that, is that normal, right?

1:09:27I appreciate you being an advocate for me and pushing back. Can you help me understand if we can lift this to be more equitable, right? I'm using information I gathered for them and I'm not just beating them up with it. I'm just saying like, you said we treat this fairly, prove it

1:09:44Lenny Rachitsky:or prove to me that you lied and this and this works is what you're saying because that like if i was the hiring manager be like no i'm sorry that's just not how it is i mean in in many cases it can be right but i'm trying to 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.

1:10:19This should also give you confidence to negotiate in the first place. You are at such a disadvantage. I just wrote an article on the game of werewolf as an example about how important information is. The game of werewolf is pretty simple. Say there's 12 people sitting in a room. Two, three of them are werewolves. right they draw a card at random three people two people whatever they get their card and they know they're werewolves there's a day and night scene and the werewolves get to reveal themselves to each other so they say oh you're a werewolf okay we're werewolves right then they go round by round and they politic to vote somebody off of the table right only two two three people understand right when the werewolves reach parity with the villagers the werewolves win right in even a like a six to one or a five to one situation, werewolves win 60, 70 % of the time.

1:11:14It shows the power of information. They understand everyone else is clueless. They know who's dangerous. They know who's not. And that's just a, that's an outnumbered situation. Now these companies have significant leverage over you. They know what people make. They know what others make. They know what they'll accept. They know their budgets. They know how to change 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. So if you are hiring manager Lenny and you put your director hat on, like it's easy to deny somebody like that because it's a little bit easier to find another product manager a little bit, right?

1:11:50If 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?

1:12:18Lenny Rachitsky:Let's try to summarize maybe the top five tactical tips that you've shared. If we're just to kind of go through and bullet points, just things people should keep in mind when they're trying to negotiate. Like one that comes to mind is don't speak, don't share the number first. Try to get them to share a number first is that is that right yeah you also have to know how to respond if they share the number first i'd rather no numbers be discussed if you're open to just waiting it out and seeing so important pieces uh so the first one is you'd never be so sure of your worth that you wouldn't accept more that's i think chris boss quotes that quite frequently uh 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.

1:13:07That's lazy, right? One brief example of this, I had a chief revenue officer and they were paid$350 ,000 base salary, 350 ,000 bonus. So 700 ,000 cash potential each year. So that's called on target earnings. They'll make 700. When we negotiated their severance, we said we wanted 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 ,500. So they cut his severance in half by doing that. Now, his response was, I'll just tell the CEO, let's up that 90 and it'll be down 90.

1:13:52He was going to split the difference to like 260 or something, whatever the math is out to. And I said, instead, simply ask, was that a mistake? right you know we had discussed on target earnings that was intentional was that a mistake he said oh yeah must have been let me just tell the attorneys to fix it feel free to redline it so he almost lost 90 grand just splitting the difference if not more right and then turns out 12 months later he got fired and then he was able to recoup 350 000 over six months so little things like trying to split the difference uh too early can be painful so that was two points i think i I know this is parts I'm bad at, trying to get a list of five.

1:14:30Lenny Rachitsky:This is great. 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 and ethos pathos logos. and so I've mentioned a little bit of this in their more common tone of logic, credibility, and emotion. Timing is another one that we don't often talk about. Kairos is important. But too many executives lean on credibility and logic because we're trained to do that. We don't show emotion. We don't show the authentic side of ourselves in corporate.

1:15:14I 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. I think there's a greater need there. The emotional side is where a lot of deals get unfair. So if we understand how to tap into that, I want to say Chris Voss, I keep mentioning Chris Voss, but I think he calls it like tactical empathy, right? Which does, that sounds more Machiavellian than anything I've ever said, right? But understanding those motivations and understanding how to play on that can be important, right? So when we talk about giving people a positive reputation, we're playing into some emotions here.

1:15:47So if I'm a female negotiating with another female, I might say, you know, I appreciate that you've always been an advocate it for women and you support one another. Like that's something I respect about you. Right. And then their cop comes in lower than a man's comp. You can call them out on that and say, if you were in my shoes, what would you do? That's one of my favorite lines. If you were in my shoes, like go backwards five years in your career. That's where I'm at right now. If you were in my shoes, what would you ask for? I love that when negotiations stall also, right? Like, you know, what's possible here.

1:16:20You 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 can be difficult in a Zoom. You and I are kind of face-to-face. We have this problem between us, right? That's an adversarial position. I want you to physically pretend that you're in the same room and I walked to your office and I put my arm around you if you're comfortable with it. And I'm, instead of us arguing over something, we're whiteboarding a solution together.

1:17:01I want collaboration. And that's how we break down walls and barriers because you're sharing information. I'm sharing information, those types of things. The, I think that was four, Maybe it was five. Another one is make it about we, not about me. Right. So another severance conversation with a chief marketing officer. This is a hundred and$200 million private company a couple of years ago. So she comes in, she gets offered$340 ,000 base salary, 30 % bonus equity. Right. We tried to push on all that. And the CEO said, look, one of the things I pride myself in is that everyone here has$340 ,000 base, 30%, and the same equity package.

1:17:48Everyone on the executive leadership, right? 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, right? And so we asked, like, standards about six months, maybe plus another month for every year served. and the CEO's like, oh, we've never done that before. And so instead of it being like, you're negotiating the terms of your divorce before you get married, that's what's awkward here. We said, well, given that we've had a problem with talent being poached 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?

1:18:36And then we fed that idea to the CEO so the CEO could look like the hero. More importantly, when my client came into that company, she looked like a hero because everyone's like, that's the woman that negotiated us all severance protections. Right? So we made the company, we used the company's equitable policies to do that. Now, I will say that's not common. Right? So folks are like, man, that's fantastical. That may not happen. Like, especially with private equity, it usually doesn't. Right? There are ways that we want to appeal to humanity more so if we can. um bonus point i know i'm monologuing a lot don't be afraid to get creative like creativity is interesting and one time we got someone a g-wagon after being like maxed out on comp i like this story because it's so out of this world that you're not going to get a g-wagon 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 like a first world problem right like tiny violin 2.4 million a year this CEO deal.

1:19:40And she told me, and this was just a joke. Like this wasn't some Machiavellian plan. She was like, look, I don't know which to choose. They're both maxed out. And I was trying to say, which one would you like more? She wasn't giving me anything. Right. They're both fine, whatever. I, and I said, well, I don't know. What kind of car do you like? Right. And, uh, she, she's all, I love Mercedes. Right. And I was like, tell them that like jokingly, because they, they inevitably came to look what's it going to take to hire you and she's like i don't know like oh maybe a company car and they said well what kind do you like and then she said mercedes and they're like done what model and then she's like oh a g-wagon and what happened was all the budgets were capped but it was a company write-off to have a six thousand pound vehicle so it was a 350 000 car added to her contract there was a company right off that reduced the tax expense so like that's not going to happen i don't suggest people go ask for g wagons but the fact is we came to a stall point

1:20:45Lenny Rachitsky:and we found a solution for that i love these stories uh another tip you should just i want to double down on is don't is don't negotiate over email make it in person as if possible or a video call, right? 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. Like you can't control whether someone's going to do that.

1:21:19Or like I said earlier, being busy at the airport, rushed through security or they just got off a call with somebody that's frustrated but if i hop into a video call and i can see that you're visibly frustrated like if for whatever reason you look like your toddler kept you up all night i'd say hey lenny would you like to reschedule to a time that feels more comfortable for you right so that we can get the most out of our time together like that is a blessing right you couldn't do that over email say things actually do fall apart say you just

1:21:48Lenny Rachitsky:pushed too hard and they're just like, okay, we're going to move on with another candidate where they make you an offer and they just, they rescinded or they promise something and they don't deliver. How do you approach when things go sideways? A couple, couple elements of that sort. One, the not delivering pieces, that's more common. Rescinded offers. I have never had a client with a rescinded offer. What I will get is a no, this is a top, take it or leave it right fine they go they get an ultimatum fine i have however helped somebody they weren't a client c also a cmo and she she was offered an 800 000 contract total cash wise and it was rescinded and so i i took this case on pro bono i got a phone call i was like i just want to see how this plays out.

1:22:39Right. And she was in tears. She lost this deal. She turns out she had a career coach that said, you need to negotiate like a white man. Like that was her advice. Like you need to be aggressive. You need to do this. You need to do that. Like you need to negotiate for your worth, which, you know, I understand the appeal of that as like, if I would understand like a woman that wants to negotiate like a man and get hers, I respect that. Right. In this situation, the context that was missing is that she was negotiating with other women. So she was negotiating with a female CEO and three other females on the executive leadership team.

1:23:14And 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, right? And I commended her for that. And so what we did was I said, look, call the CEO, explain what happened, share that, you know, obviously it's important that women take care of each other, right? And it's clear to me that you have, there's that positive reputation, right?

1:23:52I 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 boom shared identity right they all know all women know this together collectively this is a shared identity tribe thing right i made a mistake and i 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 it's like that was the path that we there was two phone calls to come up with that idea.

1:24:30She got that deal back on the table is now happily making 800 ,000 a year. Right? So when things go south, approach it with honesty, integrity, say like, I made a mistake. Take ownership. Extreme ownership really helps here. That could probably be one of those, those points. When you fail to live, 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.

1:24:56Lenny Rachitsky:That is so, I love that approach of just like, okay, I hired this coach. They gave me bad advice. It made me feel good too. I was like, should I hired me? It's interesting how negotiation is different if you're a man versus a woman. Do you take a different approach if it's a female client versus a male and it's just like, here's, you should approach it this way or it depends on the person? 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, like, or you're German, or you're, everybody is different culturally.

1:25:33So male, female, like every little nuance is, is important. If you're, you know, you're gay, or you're black, or you're, there are different challenges that everybody has to overcome. Right. And I remember this was a powerful one. I was speaking to chief. There's about 400 women in chief and I'm the I'm the white dude mansplaining to all these women about negotiations like the scariest position for me to be in and I remember there was this African-American gal and she said Jacob should we just negotiate for 84 % because that's what we're going to get anyway right like that's defeatist like that sucks to have that feeling right now I don't know what that feels like like I have I have done fairly well for myself and there are some advantages that I had.

1:26:20But I said, look, how many of you in here are mothers? Many of these women raise their hand. 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. And it kind of 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.

1:26:55There's a big power imbalance, right? Here's the founders coming in again, like, Jacob, don't tell them to do that. I don't want to revolt, right? Take care of them, right? Push back because a rising tide raises all ships, right? If companies want to rely on precedent, have the audacity to raise the precedent because the next people in line will will do that to the point about collaboration this was actually with uh one of your readers that read the that first article we did um we made a lot of money on this deal and they came to you to work with you oh i love this yeah so this is fun um but so this is kind of like a private equity hostile takeover situation and this reader of yours was getting pushed out of the company and if you try to go head to head with the pe you're going to lose right?

1:27:43He had a great relationship with the CEO, 10-year relationship. But the CEO wouldn't take any action to support him, right? Until we made it about we. The CEO had made comments that I'm probably going to get fired too, right? So what we did was we talked to the CEO and we said, whatever precedent you help me deliver, you're going to get two to three times that. So we need to set this up, right? So then they were full on. You had the CEO and the CPO putting together a game plan to advocate against the private equity, right? To support that transition plan. We got a retention bonus and a severance bonus on the table because of that, right?

1:28:21Because now the CEO is protected as well, can point back to some precedent, right? So not everybody does it out of the goodness of their heart, not in a capitalist society, right? You have to show them your motivations here are important, right? So women negotiating, if you want women after you to have 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, right?

1:28:53Let's all push for those to help and make it easier for everyone.

1:28:56Lenny Rachitsky:I love this point you made about how there's no one way to approach this. The way I was originally thinking we'd do this chat is like a step-by-step guide to negotiating. Here's what you do. One, two, three, four, and this is how your comp goes way up. 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. That was one of the things that was hard about the article we wrote together was that I have gains, right?

1:29:31It'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 you're like i don't have a gun to my head i just have 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 like very academic.

1:30:06And 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? Like those things are all very true, but it comes off intimidating. Right. And when we, 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, right? If you're reaching a block, why does that block exist? If you don't know the answer, you haven't asked the right questions, right? You don't necessarily know.

1:30:43It's an information imbalance that you have. And really what negotiation comes down to information and timing, that's what creates power, right? Those are the three things. That's all you need to know. You have to have the information. When we were talking about that game of werewolf, even when you're outnumbered five to one if you have more information the odds are you'll win right so i don't want it to be overly complicated one of the i i guess i have to say so i'm trying to write a book this year i'm gonna write it right i'm gonna write it now must happen now it must happen i know like i just kind of clenched up a little bit because like i gotta i gotta do it it's not early in the year you got so much time oh yeah thanks right i'm a prolific writer i'll get after that.

1:31:27But the book title is called Predetermined. And I wanted it to be predetermined like with a question mark, right? Because none of these outcomes are predetermined. No matter what situation you are in your life, how you were raised, it 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. And one of my favorite things to ask somebody, and they're like, oh, Jacob, I want to do this in five years. I'll say, what would that look like if it was done in one?

1:32:05What must be true? And like truncating that experience, just to think through it, not necessarily that I'm asking them to rush through it or whatever. But I have clients that they'll have 10 or$15 million 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? Like, if I had a million dollars, I would retire. Like, give me a break. Like, that seems like so much money to me. Why is that the case? Right? Um, so I like to challenge those, those notions there. Right. Um, it's an important thing to think about. Like, 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?

1:32:47Maybe a minimalist or stoic type philosophy. One of these Hollywood deals we did, uh, we had a director and a marvel superhero that got in a spat on a big franchise this is a estimated 500 million to billion dollar franchise opportunity this a-list celebrity uh and their writer uh on this third installment of a movie didn't like it so i 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 right offended the original director because they wrote the first two movies and they were very successful right to build this franchise so pissed off right next writer comes in this is worse than the one before can we just hire back the first one and get work through it right so 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 like to get him to say yes here's a million more dollars right didn't do it like a million dollars wasn't enough to mend this relationship the important lesson here is it's not always about money that individual was making 10 million dollars a year a 10 increase to have to go back to somebody they didn't like not powerful right my suggestion was can you ask the actor this a-list celebrity to humble themselves and apologize and that is what moved the deal across the line actually came in and apologized for the behavior it's not going to be like that that's what got the deal back together and the million dollars was saved so it's not always about money i use a lot of money in the stories because it's kind of shock and awe it's like wow like that's going to have big impact like at the end of the day if you're making 18 an hour and you negotiate to 24 like such a material difference in your life that is so magical to maybe be able to afford gas for the first time right and then i'm telling stories where people haven't thought about how much gas costs ever right so like there are situations i remember that i like just 10 years ago well 12 years ago i was homeless like fighting through all this stuff and didn't know if i could pay for gas so it's one of the reasons i'm inspired to do that is that you can make a material difference and it compounds throughout your life but it's not always about me.

1:35:08Lenny Rachitsky:I want to follow this Hollywood thread before we wrap up. I love that you work with Hollywood folks, celebrities, and also tech people, which is most of the audience here. Is there another wild story from your Hollywood life that might be fun to share? I think what's interesting about Hollywood is that it's so far-fetched. 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, right, which after taxes is like eight, right? And then when you look at it, it's like$400 a month or whatever.

1:35:50You're struggling to maybe ask for 10, 20 grand, right? In Hollywood, like we did this deal with, I can't share who, A-list celebrity. and the company said, we want to pay her$5 million for this movie. And the attorney came back, we want$22 million. Like, talk about being aggressive, right? And the production company's like, all right, how about 13? And this was in like a two-day span. So they went from$5 million to$13 million in two days. And the other, they're like, well instead of 22 how about 18 right like they're moving four million dollar chunks at a time and we're over here in tech going like oh i wonder if i can get 10 000 right so like that's something that i just find absolutely wild the bigger the op like this is just like you want to make money solve rich people problems right that's what happens right it's it's just escalated i can only imagine what a negotiation with like elon musk would be like you'll throw 100 billion at it and you're like oh my gosh like i also found out that a million seconds is like 11 days have you ever heard this a million seconds is 11 days do you know how do you know how long a billion seconds is like probably hundreds of years it's like 30 30 years 31 years so between 11 days that's the discrepancy between a million and a billion right and so these are just like these things scale so exponentially, it's just that what you say and how you negotiate just kind of changes.

1:37:26So if you want to really increase your comp, you do have to move rooms, right? You have to start networking and making connections with folks that can do that with you.

1:37:35Lenny Rachitsky: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 the comp? Is it just reply with, is there room for more? What's like, what should they do when they get that email? You always give me these nuanced ones, huh? So it's, they get it from the recruiter. Yeah, let's say the recruiters. That's probably right. Yeah. Recruiter is going to, again, they're probably going to have that 20 % with a room there. If you're okay with that, I might, again, just say, what's the chance we can, we can bump.

1:38:11Like, this is what I was looking for, right? I would probably, knowing that the recruiter is going to split the difference, I would probably anchor higher versus lower. There have been some studies and I was reading some, I've read a lot of negotiation books. There's like one from the 70s on these negotiation games. And those who anchored egregiously high won 75 % more than those who just tried to be reasonable. 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 have got 15, right? So if you are going to re-anchor, just say, hey, I was kind of in the ballpark of this.

1:38:52Again, with the nuance, you may have already committed to a range before, and it can be difficult to have that conversation, right? So I might say, hey, after we've had the conversations with the hiring manager and yada, yada, it sounds like the scope of the role has increased. Are you open to revisiting the comp structure on this? That's likely how I would respond. Now, 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.

1:39:26Are 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? Like, 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. That will not work. And I've noticed this in our back and forth in your emails. Like, you'll respond with two words. That's all you need, right? You don't often need more. So, like, the more confident you get, the shorter your communication gets.

1:39:56And 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. hopefully that was tactical enough if it's not i do have a 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 right i do have written scripts and guides for this and i have a free course on how to do this too that's on youtube so it's not like you're uh if you need the actual specifics there are a lot of scenarios i've already kind of covered you can go amazing and

1:40:29Lenny Rachitsky: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. You share all of this stuff out there. You have this free course. You have all these sub stack posts. So that's what I love about you. It's not like some deal leaf flow here. 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 unobtainable.

1:41:09So 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. I just, I felt a little powerless growing up. There's like some little substance abuse and trauma as I was growing up and I never felt comfortable or safe. And so when I became a little older, I started to understand psychology a little bit differently because the same fear I'd have as a child, I could see in the boardroom. I could see the same fight or flight mechanisms, but that was far less scary. Right. So it's just money. Money is like, I'm not going to get hit.

1:41:48Right. Nobody's going to get hurt here. Right. So I could start to see that and I could see the body language and I can understand when somebody was in a tense moment. and all I ever wanted to do, because I felt that from a little kid, was help that person feel safe. Help them feel safe in that moment. 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.

1:42:17Lenny Rachitsky:There's a whole other conversation we could have about that whole part of your journey. We got to be careful about that one. I might start crying on that one. Okay, well, that makes good content. That could be part two. That'll be the comments. Like, next time, make Jacob cry, Lenny. Go for the kill. Go for the kill. I hope not. I don't think my people want that. We'll see. Oh, my God. Okay, before we get to our very exciting lightning round, Jacob, is there anything else you want to share? Anything else you want to leave listeners with? If you're going to take a chance, take a chance on yourself.

1:42:53I'm sure a lot of these folks are parents, A lot of these people are parents and you want to be the best version of yourself and show that your kids think 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. 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 right if you're afraid of wealth this is something that really screwed me up like i used to despise wealth it despised it right and i don't know why it was like miss like i didn't trust people with money i felt like they all had to be dirty or they all had to do something and to be fair a lot of people do things that are highly questionable and unethical, right?

1:43:53And we see that in the world around us. But if you fear it and you don't understand it, you'll never have an opportunity to change it. And so you need to take some chances on yourself with this. And hopefully that's another piece, just having the confidence to go out and try. Even if you fail, you're failing forward. You're learning, right? You're going to find a style that works best for you. It's not that Jacob Warwick's style is the style that's awesome or Lenny's style is the style. You don't need to copy anyone else. You need to find that center that works well for you and what you're comfortable.

1:44:24Lenny Rachitsky:That is beautiful. I'm also realizing as we're talking, we haven't mentioned AI once in this conversation, which is incredible. The listeners are like, oh, thank goodness. Yeah, that's how I feel. Right? Thank goodness. Just once in a while. It's because I don't want AI to replace me, Lenny. I don't want it. Yeah, I don't even know. Anyway, oh we're kidding okay i got you speechless that's the job if you get the podcast host speechless you're doing your job that's great okay well we did it with that jacob we have reached our very exciting lightning round i've got five questions for you are you ready all right i will i'll do the best i can yeah here we go what are two or three books you find yourself recommending most to other people influenced by robert cialdini that's the one that's the one i mean i like uh herb cohen's you can negotiate anything it's a little dated uh like old white dude in the 80s dated so be mindful it doesn't suit all audiences but it's what i like about it is they talk about like negotiating dishwashers and stuff not like going to market with meta versus instagram and the acquisition, like it's not complicated.

1:45:39It's like, here's an apple and here's an orange. And here's the concept of negotiation really spelled out simple. Um, 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, like, this is what I wanted to write. So I was frustrated. And then I was like, I'm going to reach out to him because I have a lot of respect for him. So I did his podcast. That'll be live soon. But yeah, that was negotiation made simple. It really breaks it down in an easy way.

1:46:14And that could be like a Bible. And then I like radical candor. I know some of your guests put that on. I've met Kim Scott. She's phenomenal. 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.

1:46:35Lenny Rachitsky:I think Radical Candor is the second most mentioned book on this podcast behind high output management. Yeah, I have not read that. Admittedly, I'm bad at consuming content. I'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. That's a great framework. Okay, next question. Do you have a favorite recent movie or TV show you've really enjoyed? i've been really liking watching luca the disney movie uh having a toddler and a newborn i really just watch cartoons now so i actually for low stimulating things i really like minuscule uh 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 um it sounds not a not appealing but no that's why it's so good because you're so overstimulated having kids that it's so mellow you can be like oh i actually get to think a little bit you know like you know finding finding a little boredom and creativity that's how you get creative if you're constantly if it's like coco melon and Paw Patrol and you're like you can hear the beats in your head like you can't do that I'm not gonna I'm like I can't do that to my kids uh favorite recent product you've discovered that you love Cloud Cowork I mean I did one I love Cloud Cowork I'm sorry for mentioning AI but like I really only use a handful of products so uh Cloud Cowork is one of them and uh macro factor for macro tracking.

1:48:22And, uh, I got a whoop this last year and I've lost almost 50 pounds, just paying attention to my whoop stats and like trying to sleep. And you could tell I'm a pretty obsessive guy. So data like still geeks me out a little bit on that. But, uh, those are the three products that I would use every day. And, and a little bit of Gemini too. Those are the two, in my opinion, winning the race.

1:48:43Lenny Rachitsky:Do you have a favorite life motto that you find yourself coming back to in work or in life? Always give more than you expect to receive. It's like a golden rule, plus plus. That's how networking works. You don't network with someone trying to take. You say, how can I help you? And that's a principle from Cialdini also, right? And how to win friends and influence people, right? That's not why I do it. I'm just suggesting that's an area where you can read more on that. Final question. You're starting a foundation, a nonprofit? it yeah i'm i'm working for or i i'm on the board of the cody de roof 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 were not really accepting that um but in with our foundation we help rural parts of Montana and get access to the healthcare that they need.

1:49:53Yeah. And so they, they got me with this. So like we, we helped this family, this, 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.

1:50:31And we funded the life flight to Denver Children's Hospital to get that life-saving surgery and saved her son's life. And that sounds like a great story. The part that got me was that now the mama feels all this guilt because she could have saved her son's life if she knew he existed in that part like i was in tears thinking about that um i did i've talked a little bit about my son's diagnosis like 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 i made a handful of phone calls i i did all this networking to be selfish and build my career and do these things and And that give before you ask it to receive philosophy, I've always kind of lived by that, undersell, over deliver.

1:51:20And 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, 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. So, like, I felt just this immense blessing and support through that. So that's the 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.

1:51:56They helped fund the life-saving medication that changes the life expectancy from 7 to 70 years old. They are expected to have full lives now. So that's something that I'm very passionate about.

1:52:07Lenny Rachitsky:Incredible. Oh, man. There's so many topics and directions we could have gone with this. Jacob. I know I blew you out. I blew you out of the water, man. Sorry. I monologue like nobody's business. I've had worse. Okay. Where can folks find you online if they want to reach out? Maybe follow up on some of this stuff. And how can listeners be useful to you? Listeners can be useful just by advocating for themselves. Rising tide forever. that's important. I don't, I guess I don't really have social media. I deleted LinkedIn. The post I wrote about that kind of went viral on Substack, which is cool. I share, I think I shared that one with you.

1:52:50I have execsandthecity.com, which yes, is a play on Sex and the City. It's kind of explaining some of the things that people are afraid to talk about. So Execs and the City is my Substack. And I write once a week on Thursday morning and I share little thoughts on what's happening occasionally i'll share case studies on what clients have done i'll share play-by-plays and the actual scripts that's also where i have a free job search course about eight hours that i filmed i used to sell it for like a grand and now i just give it away for free that's also available on the youtube which is execs in the city which i have like 100 subscribers so don't expect a lot of content from me i'm not i'm not pumping out video content all the time um and then there's a a small paid tier.

1:53:34If somebody wants to get discounts on coaching, they also get access to Jacob GPT. Well, so another AI mentioned that's digitally trained on, I think you have one too, right? Yeah. It was like trained on all my content. Lenny bot. Yeah. So it's, it's like a Jacob bot, which is a minor Lenny bot, right. Trained on my content. And, um, then I do some additional case studies for them. Uh, and then my actual business is think warwood.com, uh, which just tells you outcomes that, 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 sub stack only, really.

1:54:10Lenny Rachitsky:Jacob, this was awesome. Thank you so much for being here. Thank you, Lenny. I appreciate the time today. And again, I was real giddy about it. And your motto was to have fun. I had a lot of fun today. Thank you. That's right. Here we go. People don't see this if they're waiting till the end of this podcast. I have this little pocket. I show all the guests their goal is to have fun. So Easter egg. All right, Jacob. Thank you so much. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.

1:54:38Lenny Rachitsky: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 Lenny'sPodcast.com. See you in the next episode.