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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\u2019s 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\u2019s 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:

\u2022 Why asking for what you want is so impactful

\u2022 Three steps to effectively ask for what you want

\u2022 Challenges that arise when people struggle to ask for what they want

\u2022 Why hearing \u201cno\u201d is a normal part of the process

\u2022 The \u201cdream behind the complaint\u201d technique for uncovering desires

\u2022 Kenneth\u2019s experience of being fired three times from Slack

\u2022 How embracing fear and discomfort is key to getting what you want

\u2022 Why discipline is overrated

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\u2022 Sidebar\u2014Accelerate your career by surrounding yourself with extraordinary peers

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Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger

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Where to find Kenneth Berger:

\u2022 X: https://twitter.com/kberger

\u2022 Threads: https://www.threads.net/@kberger

\u2022 LinkedIn: https://www.linkedin.com/in/kberger/

\u2022 Website: https://kberger.com/

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Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 X: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Kenneth\u2019s 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 \u201cno\u201d is a normal part of the process

(17:29) Getting a \u201cyes\u201d vs. a \u201chell yes\u201d

(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\u2019s 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

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Referenced:

\u2022 Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager

\u2022 Internal Family Systems: https://ifs-institute.com/

\u2022 How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, \u201cTouchy Feely\u201d): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

\u2022 Leaders in Tech: https://leadersintech.org/

\u2022 The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

\u2022 T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup

\u2022 DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man

\u2022 Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt

\u2022 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

\u2022 Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/

\u2022 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

\u2022 Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

\u2022 Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

\u2022 Jonny Miller\u2019s Nervous System Mastery course: https://nsmastery.com/lenny

\u2022 Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout

\u2022 The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE

\u2022 Break Point on Netflix: https://www.netflix.com/title/81569920

\u2022 Living on Netflix: https://www.netflix.com/title/81582076

\u2022 Wimbledon tennis: https://www.wimbledon.com

\u2022 Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820

\u2022 Tea From Taiwan: https://www.teafromtaiwan.com/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.