Lenny's Podcast: Product | Career | Growth

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

May 19, 2024

AI Summary

5 min read

Kenneth Berger, the first product manager at Slack and now an executive coach for startup leaders, explains how the skill of asking for what you want addresses common pitfalls like burnout, stuckness, and interpersonal conflict. Rooted in maintaining personal integrity, this practice reduces self-deception and suffering by aligning actions with desires, even without guaranteed outcomes.

Spotting the need and clarifying desires

People often overlook this skill if they're stuck repeating ineffective approaches, facing repeated conflicts, or treating situations as life-or-death high stakes that fixate on fears rather than goals. People-pleasers avoid asking to keep others happy, while control-oriented types demand compliance. To articulate wants, start with complaints as clues to underlying dreams—envision the better future they imply, then check if it's inspiring yet credible (not embarrassing or "fine"). Tune into subtle emotions or unexpressed thoughts for integrity; avoiding this leads to bottled frustration.

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What you'll learn

1 `* (00:05:19) **Why "Ask for What You Want" is Core to Integrity and Success**`
2 `* (00:09:17) **Signs You Need to Improve: Stuckness, Conflict, High Stakes**`
3 `* (00:11:15) **Figuring Out What You Want: Dream Behind the Complaint**`
4 `* (00:14:29) **The 3 Steps: Articulate, Ask Intentionally, Accept Response**`
5 `* (00:19:32) **Articulating Wants Effectively: Examples from Feedback & Alignment**`
6 `* (00:27:12) **Asking Intentionally: Phrases, Humility, Influence Without Power**`
7 `* (00:36:40) **Overcoming Resistance: Embrace All Parts, Feedback Frameworks**`

+ Full timestamped outline available in the app

Show Notes

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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