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Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM @Slack)

Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore: • Why asking for what you want is so impactful • Three steps to effectively ask for what you want • Challenges that arise when people struggle to ask for what they want • Why hearing “no” is a normal part of the process • The “dream behind the complaint” technique for uncovering desires • Kenneth’s experience of being fired three times from Slack • How embracing fear and discomfort is key to getting what you want • Why discipline is overrated — Brought to you by: • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers: https://www.sidebar.com/lenny • Webflow—The web experience platform: https://webflow.com • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript and references at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger Where to find Kenneth Berger: • X: https://twitter.com/kberger • Threads: https://www.threads.net/@kberger • LinkedIn: https://www.linkedin.com/in/kberger/ • Website: https://kberger.com/ 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) Kenneth’s background (04:31) The importance of asking for what you want (06:36) Challenges that arise when people struggle to ask for what they want (08:09) A personal example of failing to ask for what you want (09:17) Signs this is a skill you need to work on (10:49) How to get better at knowing what you want (15:28) Why hearing “no” is a normal part of the process (17:29) Getting a “yes” vs. a “hell yes” (19:20) Step 1: Articulate what you want (24:07) Doing an integrity check (26:56) Step 2: Ask for what you want intentionally (30:45) Understanding your influence (34:48) Using complaints as inspiration (36:24) Internal family systems (38:00) Giving feedback (41:24) Step 3: Accept the response (45:22) Kenneth’s experience of being fired three times from Slack (57:30) Advice on being the first PM at a company or startup (01:04:58) Contrarian corner: anti-discipline (01:05:52) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Lenny RachitskyhostKenneth Bergerguest
May 18, 20241h 13mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Unlocking Career Fulfillment By Simply Asking For What You Want

  1. Kenneth Berger, former first PM at Slack turned executive coach, argues that most career and life dysfunction stems from not clearly asking for what you want—and not being able to hear the true response. He lays out a simple but demanding loop: articulate what you want, ask for it intentionally, and fully accept the response (usually a no) as data, not a verdict. Berger illustrates how people-pleasing, control-freak tendencies, fear of conflict, and attachment to being right all block this skill, sharing his own story of being effectively fired three times from Slack as a case study. He emphasizes integrity, emotional regulation, and shifting from fear-based motivation to vision-based motivation as the path to sustainable high performance and fulfillment.

IDEAS WORTH REMEMBERING

5 ideas

Use your complaints to uncover what you really want.

Every complaint implies a dream of a better reality; instead of dismissing or suppressing complaints, treat them as raw input, then explicitly articulate the improved outcome you’re actually longing for.

Articulate your desires clearly before you ever ask.

Most people skip straight to action or avoidance without naming what they want in plain language; taking time to define the outcome you want—beyond ‘it’s fine’ or unrealistic fantasies—aligns your actions with integrity.

Ask intentionally: be direct, humble, and relationship-aware.

Avoid both mind-reading (never asking) and entitlement (ordering); instead, state what you want plainly, acknowledge it may not be the other person’s call or preference, and invite their honest response.

Treat anything short of a ‘hell yes’ as a no—and explore why.

Lukewarm maybes lead to missed deadlines, flaked commitments, and resentment; when you sense hesitation, explicitly ask, “What would make this a hell yes for you?” to uncover true constraints and build reliable agreements.

Accept responses as data, not judgments on your worth.

Most asks will get a no, and over-accepting (“it’s no forever”) or under-accepting (“they said no but I’ll push anyway”) both backfire; emotionally regulating around no lets you learn, iterate the ask, or try somewhere else.

WORDS WORTH SAVING

5 quotes

Every complaint implies a dream.

— Kenneth Berger

It’s not a yes unless it’s a hell yes.

— Kenneth Berger

All you have to do to turn it around is ask for what you want.

— Kenneth Berger

I spent that year being fully out of integrity with myself.

— Kenneth Berger

Fear is for when there’s a tiger chasing you—and there’s no tiger in the room.

— Kenneth Berger

The core skill of asking for what you want and why it mattersHow to figure out what you actually want (complaints, dreams, integrity)Effective ways to ask: clear, humble, direct, and relationally awareAccepting and interpreting responses (especially no and non–‘hell yes’)Managing fear, resistance, people-pleasing, and control-freak tendenciesKenneth’s Slack story: being fired three times and lessons on integrityImplications for founders, first PMs, and high-achieving professionals

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