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

Kim Scott

Radical candor really gave me the confidence to be assertive in the ways that I never had been before.

John Lowry

I did just do a podcast with John Lowry and he wrote a book called negotiation made simple.

Robert Cheldini

Humans built this. This is not concrete authority. This can be influenced.

Episode summary

Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes. We discuss: 1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump 2. Why Jacob sees 40% average movement when negotiations are run well 3. When negotiation actually starts (hint: it’s much earlier than you think) 4. Why information + timing create power 5. The biggest mistakes people make when negotiating 6. How to navigate the important “What’s your comp expectation?” question without anchoring too low 7. Why the best interviews feel more like discovery calls than interrogations — Brought to you by: Orkes —The enterprise platform for reliable applications and agentic workflows Mercury —Radically different banking Omni —AI analytics your customers can trust — Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jacob Warwick: • Substack: https://www.execsandthecity.com • YouTube: https://www.youtube.com/@ExecsandtheCity • Website: https://www.thinkwarwick.com • Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jacob Warwick (04:12) How much comp people leave on the table (07:52) Why you shouldn’t feel greedy asking for more (09:45) What founders should know about negotiation (13:03) How Jacob works behind the scenes (15:35) The biggest mistakes people make when negotiating (19:30) Home-field advantage and controlling the conversation (23:02) The step-by-step approach to negotiating an offer (30:17) Jacob’s passion and why these tips don’t work on kids (32:04) Who should speak first about compensation (35:36) Understanding power (39:52) Breaking out of salary bands by focusing on pain points (45:45) Brief summary (47:20) Selling the vacation: How to visualize success (50:07) Controlling the narrative and planting seeds (59:01) Jacob’s role as hype man (01:01:05) Positioning yourself like a product (01:02:49) Making the process frictionless for hiring managers (01:06:20) Flipping the interview to extract information (01:12:17) Five tactical tips for negotiating comp (01:21:45) What to do when negotiations fall apart (01:25:05) Why negotiation is different for every individual (01:28:55) Why outcomes aren’t predetermined (01:32:52) Wild Hollywood negotiation stories (01:37:35) The first step you should take after getting an offer (01:40:30) Jacob’s personal mission (01:44:42) Lightning round and final thoughts — Referenced: • The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating • Sam Altman on X: https://x.com/sama • Tom Brady on X: https://x.com/TomBrady • Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8 • Salesforce: https://www.salesforce.com • Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts • Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon • Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that • Chris Voss on X: https://x.com/fbinegotiator • Werewolf: https://playwerewolf.co • Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion • How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy • ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation • Marvel: https://www.marvel.com • Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030 • Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0 • Minuscule : https://www.youtube.com/user/Minuscule • Claude Cowork: https://claude.com/product/cowork • Macrofactor: https://macrofactor.com • Whoop: https://www.whoop.com • Gemini: https://gemini.google.com/app • The Cody Dieruf Foundation: https://breathinisbelievin.org • Cystic Fibrosis Foundation: https://www.cff.org — Recommended books: • Negotiation Games : https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941 • Influence: The Psychology of Persuasion : https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X • You Can Negotiate Anything: How to Get What You Want : https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229 • Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal : https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325 • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity : https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • High Output Management : https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • How to Win Friends and Influence People : https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034 — Production and marketing by https://penname.co/ . For inquiries about sponsoring the podcast, email [email protected] . — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Mention timeline

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Kim Scott

The host mentioned 'Radical Candor' as a pivotal resource that helped him gain confidence in being assertive, which h…

John Lowry

The host mentioned 'Negotiation Made Simple' as a book that effectively simplifies the concept of negotiation, making…

Robert Cheldini

The host discusses the importance of information asymmetry in negotiations, highlighting how companies often have mor…

Extreme Ownership

The host mentioned 'Extreme Ownership' to emphasize the importance of taking responsibility in negotiations, especial…

Predetermined?

The host mentions 'Predetermined?' to emphasize that outcomes in negotiation are not fixed and can be influenced by v…

You Can Negotiate Anything

Erb Cohen

The host mentions 'You Can Negotiate Anything' to highlight its straightforward approach to negotiation, despite its…

Getting to Yes

The host mentions 'Getting to Yes' to highlight the complexities and academic nature of negotiation frameworks. They…

How to Win Friends and Influence People

The host mentions 'How to Win Friends and Influence People' as a foundational text for understanding networking. He h…

negotiation strategies(2)assertiveness in communication(1)negotiation challenges(1)negotiation complexities(1)negotiation tactics(1)negotiation techniques(1)networking principles(1)

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The conversation centers on negotiation strategies.
A second recurring theme is assertiveness in communication.
Referenced books include Radical Candor by Kim Scott and Negotiation Made Simple by John Lowry.
The strongest audience signal points to Professionals seeking to improve communication skills and Individuals looking to improve their negotiation skills.

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Deep Dive(3)Critical Analysis(2)Highly Recommended(2)Passing Reference(1)

Audience signals

Professionals seeking to improve communication skillsIndividuals looking to improve their negotiation skillsProfessionals looking to improve their negotiation skillsProfessionals navigating negotiation dynamicsindividuals seeking to improve their negotiation skillsIndividuals interested in learning basic negotiation skills.

Books Mentioned

The full list below is ranked by how useful each mention is to a listener: stronger recommendation language, clearer quote context, and better timestamp support rise first.

Kim Scott

Best for Professionals seeking to improve communication skillsOften cited around assertiveness in communication

“rb Cohen's you can negotiate anything. It's a little dated, like old white dude in the 80s dated. So be mindful. It doesn't suit all audiences. But 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. It's like here's an apple and here's an orange and here's the concept of negotiation really spelled out simple. I did just do a podcast with John Lowry and he wrote a book called negotiation made”

View mention details

Sentiment: Highly Recommended

Trigger: assertiveness in communication

For: Professionals seeking to improve communication skills

Key quote: “Radical candor really gave me the confidence to be assertive in the ways that I never had been before.”

The host mentioned 'Radical Candor' as a pivotal resource that helped him gain confidence in being assertive, which he previously struggled with. He highlights the book's impact on his career and its relevance in the corporate world.

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John Lowry

Best for Individuals looking to improve their negotiation skillsOften cited around negotiation techniques

“etting to. 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 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 Cheldini. That's the one. That's the one. I mean, I like Erb Cohen's you can negotiate anything. It's a little dated, like old white dude in the 80s dated. So be mindful. It doesn't suit all”

View mention details

Sentiment: Highly Recommended

Trigger: negotiation techniques

For: Individuals looking to improve their negotiation skills

Key quote: “I did just do a podcast with John Lowry and he wrote a book called negotiation made simple.”

The host mentioned 'Negotiation Made Simple' as a book that effectively simplifies the concept of negotiation, making it accessible to a broader audience. They expressed admiration for the author, John Lowry, and noted their desire to write a similar book, indicating the impact it had on them.

Amazon search results · affiliate link

Robert Cheldini

Best for Professionals looking to improve their negotiation skillsOften cited around negotiation tactics

“d 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 and it is for middle managers or lower. So if you are hiring manager, Lenny and you put your director head on, like, it's easy to deny somebody like that because it's a little bit easier to find another product manager. a little bit, right? If we do our job to differentiate, then we're doing better”

View mention details

Sentiment: Deep Dive

Trigger: negotiation tactics

For: Professionals looking to improve their negotiation skills

Key quote: “Humans built this. This is not concrete authority. This can be influenced.”

The host discusses the importance of information asymmetry in negotiations, highlighting how companies often have more leverage than individuals. They reference the book 'Influenced' to emphasize the power of persuasion and influence in achieving equitable outcomes.

Amazon search results · affiliate link

Extreme Ownership

Best for Professionals navigating negotiation dynamicsOften cited around negotiation challenges

“EO, explain what happened, share that, you know, Obviously, it's important that women take care of each other, right? And it's clear to me that you have, there's that positive reputation, right? I got to be honest with you, I hired a coach to try to understand what to do because in the past, I failed. In the past, I haven't been my best advocate. In the past, I've done less. I suspect you know what that's like. Boom, shared identity, right? They all know. All women know this together, collective. This is a shared identity tribe thing, right? I made a mistake and I, I, I disagreed with the advice, but I did it anyway because I had to”

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Sentiment: Deep Dive

Trigger: negotiation challenges

For: Professionals navigating negotiation dynamics

Key quote: “Extreme ownership really helps here.”

The host mentioned 'Extreme Ownership' to emphasize the importance of taking responsibility in negotiations, especially when things go wrong. This concept is highlighted through a real-life example where a woman regained a rescinded job offer by being authentic and transparent.

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Predetermined?

Best for individuals seeking to improve their negotiation skillsOften cited around negotiation complexities

“ou're reaching a block, why does that block exist? If you don't know the answer, you haven't asked the right questions, right? You don't necessarily know. It says that 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 guess I have to say it. So I'm trying to write a book this”

View mention details

Sentiment: Deep Dive

Trigger: negotiation complexities

For: individuals seeking to improve their negotiation skills

Key quote: “none of these outcomes are predetermined.”

The host mentions 'Predetermined?' to emphasize that outcomes in negotiation are not fixed and can be influenced by various factors. They highlight the importance of curiosity and empathy in the negotiation process, suggesting that understanding these dynamics can lead to better outcomes.

Amazon search results · affiliate link

You Can Negotiate Anything

Erb Cohen

Best for Individuals interested in learning basic negotiation skills.Often cited around negotiation strategies

“awesome or Lenny's 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. That is beautiful. I'm also realizing as we're talking, we haven't mentioned AI once at this conversation. Oh, no. Which is incredible. The listeners are like, oh, thank goodness. Yeah. That's 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. I. Yeah. Like, I don't even know. Anyway, we're getting to. 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”

View mention details

Sentiment: Critical Analysis

Trigger: negotiation strategies

For: Individuals interested in learning basic negotiation skills.

Key quote: “I mean, I like Erb Cohen's you can negotiate anything. It's a little dated, like old white dude in the 80s dated.”

The host mentions 'You Can Negotiate Anything' to highlight its straightforward approach to negotiation, despite its dated perspective. They acknowledge that while the book may not resonate with all audiences, its simplicity in explaining negotiation concepts is valuable.

Direct Amazon listing · affiliate link

Getting to Yes

Best for Individuals seeking practical negotiation skillsOften cited around negotiation strategies

“ing. 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 that's probably not real. That was one of the things that was hard about the article we wrote together was that I have gains, right? It's a process that I follow. It's not a concrete step-by-step process. But one of the reasons I'm so hesitant to go this route is because negotiation comes off so complicated. it's so complicated and so”

View mention details

Sentiment: Critical Analysis

Trigger: negotiation strategies

For: Individuals seeking practical negotiation skills

Key quote: “When we try to focus so much on frameworks and academic, we stop listening.”

The host mentions 'Getting to Yes' to highlight the complexities and academic nature of negotiation frameworks. They emphasize that while the book provides valuable concepts, real-life negotiations require empathy and curiosity rather than rigid adherence to theoretical models.

Amazon search results · affiliate link

How to Win Friends and Influence People

Best for Individuals looking to improve their networking skillsOften cited around networking principles

“. Favorite recent product you've discovered that you love? Cloud Co-Work. I mean, I did one. I love Cloud Co-Work. I love Cloud Co-Work. Sorry for mentioning AI, but like I really only use a handful of products. So Cloud Co-worker is one of them. and a macro factor for macro tracking. And I got a whoop this last year. And I've lost almost 50 pounds, just paying attention to my whoop stats and like trying to sleep. And you could tell him a pretty obsessive guy. So data like still geeks me out a little bit on that. But those are the three products that I would use every day. And in a little bit of Gemini, too. Those are the two, in my opinion, winning the”

View mention details

Sentiment: Passing Reference

Trigger: networking principles

For: Individuals looking to improve their networking skills

Key quote: “That's a principle from Chaldingi also, right? And how to win friends and influence people, right?”

The host mentions 'How to Win Friends and Influence People' as a foundational text for understanding networking. He highlights the principle of giving more than you expect to receive, which he believes is essential for effective networking.

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Radical Candor

Lenny's Podcast: Product | Career | Growth · 1:46:12

Radical candor really gave me the confidence to be assertive in the ways that I never had been before.

Negotiation Made Simple

Lenny's Podcast: Product | Career | Growth · 1:45:46

I did just do a podcast with John Lowry and he wrote a book called negotiation made simple.

Influenced

Lenny's Podcast: Product | Career | Growth · 1:45:12

Humans built this. This is not concrete authority. This can be influenced.

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Kim Scott

The host mentioned 'Radical Candor' as a pivotal resource that helped him gain confidence in being assertive, which he previously struggled with. H…

Direct Amazon listing · affiliate link

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John Lowry

The host mentioned 'Negotiation Made Simple' as a book that effectively simplifies the concept of negotiation, making it accessible to a broader au…

Amazon search results · affiliate link

Mentioned at 1:45:12