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

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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

Some takeaways:

1. Asking for what you want comes down to integrity—being honest about your capabilities, desires, and boundaries. Signs you may not be asking for what you want include feeling stuck, having frequent interpersonal conflicts, or a pervasive sense that the stakes are extremely high.

2. Learn to respect a no. This means not under-accepting or over-accepting it. Under-accepting a no is when you treat it as invalid and refuse to learn what you can from the experience. Over-accepting a no is when you treat it as too valid, to the point where you assume you’ll only ever hear no’s again in the future and therefore should stop asking for things you want. When you hear a no, learn from the experience and push forward with the understanding that you won’t always get what you want, and that’s OK.

3. Practice the “dream behind the complaint” technique: When you catch yourself complaining, use it as an opportunity to uncover what you truly desire. Every complaint implies a vision of a better scenario. After identifying the dream behind the complaint, assess its inspiring nature. Is it compelling enough to motivate you? If not, dig deeper to uncover a dream that truly excites and motivates you.

4. Aim for a “hell yes” rather than settling for anything less. Don’t be satisfied with lukewarm responses like “maybe” or “we’ll see,” as they may lead to unfulfilled expectations later on. If you do get these lukewarm responses, ask what it would take to get to a “hell yes.” This enthusiastic consent ensures commitment and passion toward a project or idea.

5. Even if you’re not a founder or in a position of traditional power, you still have influence. Whether you’re a product manager, individual contributor, or part of a team, your opinions and perspectives matter more than you might realize. Don’t underestimate the impact of voicing your concerns or suggestions. Even if you’re not the decision maker, sharing your perspective can lead to meaningful discussions and potentially influence the outcome. Be willing to express disagreement respectfully and offer alternatives or solutions.

6. There are three key steps to asking for what you want:

   1. Step 1: Articulate what you want: Get clear on your desires, dreams, and goals. If you struggle with this, look at your complaints—they point to an implied better future you envision.

   2. Step 2: Ask for what you want intentionally: Don’t expect others to read your mind. Ask clearly and directly while being open to their response. Come from a place of humility rather than entitlement.

   3. Step 3: Accept the response: Reframe a no as valuable information rather than failure. It’s not a final destination but an invitation to get curious, iterate, and try again.

Listen now on Apple, Spotify, and YouTube.

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/

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

Referenced:

• Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager

• Internal Family Systems: https://ifs-institute.com/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• Leaders in Tech: https://leadersintech.org/

• The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup

• DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man

• Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/

• How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Jonny Miller’s Nervous System Mastery course: https://nsmastery.com/lenny

• Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout

• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE

• Break Point on Netflix: https://www.netflix.com/title/81569920

• Living on Netflix: https://www.netflix.com/title/81582076

• Wimbledon tennis: https://www.wimbledon.com

• Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820

• Tea From Taiwan: https://www.teafromtaiwan.com/

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.