Lenny's Podcast: Product | Growth | Career

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

May 19, 2024

01:13:36

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Kenneth Berger, an executive coach in the tech industry and former founder, discusses the impact of asking for what you want, overcoming challenges in communication, embracing fear and discomfort for success, and the significance of living authentically. He shares personal experiences of being fired multiple times, highlights the importance of addressing desires with compassion, and emphasizes the power of joy over fear in pursuing goals. The podcast explores practical advice for personal growth and fulfillment through intentional communication and embracing all aspects of oneself.

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Quick takeaways

Clarity in expressing desires is crucial for effective communication and decision-making.

Intentional and respectful communication when making requests is essential for influencing outcomes.

Accepting responses, positive or negative, and learning from them is key to personal and professional growth.

Deep dives

Articulating what you want is key to effective communication

Step one emphasizes the importance of clearly expressing your desires. It highlights that being able to identify and articulate what you want is essential for effective communication and decision-making. The example of a product manager wanting to make a decision in a meeting but hesitating to speak up demonstrates the significance of this step.

Going for “Hell Yes”

01:22

Importance of Asking for What You Want

00:58

Exploring Personal Growth, Feedback, and Learning to Work with Others

03:06

Balancing Clarity and Humility in Asking

01:01

Introduction

4min

The Power of Asking for What You Want

18min

Balancing Kindness and Boundaries in Team Dynamics

4min

Exploring the Power of Asking for What You Want

3min

The Art of Asking for What You Want

12min

Accepting Responses and Learning from Rejection

20min

Embracing Joy Over Fear in Pursuit of Goals

8min

Exploring Tea, Healthy Drinking, and Life Advice on Asking for What You Want

2min

Embracing the Power of Asking for What You Want

2min

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

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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:

• X: https://twitter.com/kberger

• Threads: https://www.threads.net/@kberger

• LinkedIn: https://www.linkedin.com/in/kberger/

• Website: https://kberger.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

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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/

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