Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at 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• 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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe