Lenny’s Podcast: Product | Growth | Career
Technology
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
• Webflow—The web experience platform
• Vanta—Automate compliance. Simplify security
—
Find the transcript 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
—
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.
Inside Canva: Coaches not managers, giving away your Legos, and running profitably | Cameron Adams (co-founder and CPO)
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect)
Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart)
Be fundamentally different, not incrementally better | Jag Duggal (Nubank, Facebook, Google, Quantcast)
A framework for PM skill development | Vikrama Dhiman (Gojek)
Business strategy with Hamilton Helmer (author of 7 Powers)
This will make you a better decision maker | Annie Duke (author of “Thinking in Bets” and “Quit”, former pro poker player)
Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour
How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”)
Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma)
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)
A framework for finding product-market fit | Todd Jackson (First Round Capital)
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)
Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO)
How to speak more confidently and persuasively | Matt Abrahams (professor, podcast host, author, speaker)
Kunal Shah on winning in India, second-order thinking, the philosophy of startups, and more
The ultimate guide to PR | Emilie Gerber (founder of Six Eastern)
The happiness and pain of product management | Noam Lovinsky (Grammarly, Facebook, YouTube, Thumbtack)
Create your
podcast in
minutes
It is Free
Insight Story: Tech Trends Unpacked
Zero-Shot
Fast Forward by Tomorrow Unlocked: Tech past, tech future
The Unbelivable Truth - Series 1 - 26 including specials and pilot
Lex Fridman Podcast