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

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

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Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM @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: https://www.sidebar.com/lenny • Webflow—The web experience platform: https://webflow.com • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript and references 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 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.
Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM @Slack)
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  • Asking for what you want is a core skill that is crucial for achieving your goals and living with integrity, but many people struggle with it.
  • Not asking for what you want can lead to feeling stuck, experiencing interpersonal conflict, and a sense of high stakes that causes fear rather than focus on goals.
  • Complaining can be a useful starting point to uncover your underlying desires and dreams that you want to pursue.
  • Overcoming the resistance and fear around asking for what you want is a key part of developing this skill effectively.
  • Asking intentionally, with both clarity and humility, is important for getting your needs met while respecting others.
  • Accepting the response you get, whether a "yes" or a "no", is crucial for learning and growth rather than getting stuck in negative emotions.
  • Dealing with the fear of failure or rejection is a common blocker, but reframing it as an opportunity to try again in a different way can be helpful.
  • Maintaining relationships and understanding the context/state of the person you're asking is important for effective communication.
  • Articulating what you truly want, not just what you think you should want, is a key first step in this process.
  • Embracing all parts of yourself, including the "complaining" or "scared" parts, with compassion can soften resistance and help you move forward.
 
When you ask for something you're much more likely to get it
Every complaint implies a dream
What would it take to get a hell-yes
aka: a full-body yes
 
Executive coach Kenneth Berger discusses the importance of asking for what we want and the challenges that come with not doing so.
 
If you’re on the people pleasing camp, youre used to not asking. You’re hoping people are reading your mind.
“why even bother”