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Kenneth Berger

Executive Coach & Former First PM at Slack at Independent Coach

Kenneth Berger was the first product manager at Slack and spent over 10 years in tech before transitioning into coaching startup leaders. His core focus is helping leaders learn how to ask for what they want, a deceptively simple skill that he argues is at the core of most career and life struggles.

Dimension Profile

Strategic Vision 40%
Execution & Craft 45%
Data & Experimentation 25%
Growth & Distribution 20%
Team & Leadership 80%
User Empathy & Research 70%

Key Themes

ask for what you want people pleasing vs control freak complaints imply dreams integrity in pursuing what matters sustainable startup work overcoming resistance to asking

Episode Summary

Kenneth Berger, the first PM at Slack turned executive coach, presents his magnum opus: the transformative power of simply asking for what you want. He explains why people pleasers avoid asking while control freaks order people around, and how finding the middle ground of authentic asking is the key to integrity, fulfillment, and career success. His practical framework includes using complaints as inspiration to uncover dreams and learning to hear the world's response without fear.

Leadership Principles

  • Ask for what you want out loud — you're much more likely to get it, and the alternative is fooling yourself about what you're pursuing
  • Every complaint implies a dream — use complaints as inspiration to envision a better future
  • People pleasers avoid asking; control freaks order people around — the skill is finding the middle ground of authentic asking

Notable Quotes

"The core idea is ask for what you want. Turns out when you actually ask for what you want out loud, you're much more likely to get it."

— On the deceptively simple skill at the core of most career struggles

"Complaints are great inspiration. Every complaint implies a dream. Let me envision a better future. Let me think about what's an effective way to actually move towards that."

— On how to figure out what you actually want by paying attention to your complaints

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