← All Leaders

Alisa Cohn

Executive Coach at Independent / Author

Named the number one startup coach in the world by Global Gurus and top 50 coach by Thinkers50, having coached C-suite executives at Etsy, Venmo, DraftKings, Microsoft, Google, and the New York Times.

Dimension Profile

Strategic Vision 30%
Execution & Craft 50%
Data & Experimentation 10%
Growth & Distribution 10%
Team & Leadership 95%
User Empathy & Research 50%

Key Themes

difficult conversations with reports founder prenup for co-founders meeting effectiveness tactics leadership vs making people happy actionable coaching language performance management

Episode Summary

Alisa Cohn, the world's top-rated startup coach, provides extremely specific and actionable language for having difficult conversations, from denying promotions to addressing underperformance. She shares her three questions to end every meeting effectively, explains why a leader's job isn't to make people happy, and introduces the 'founder prenup' — a set of questions co-founders should discuss before committing to build together.

Leadership Principles

  • Your job as a leader isn't to make people happy — it's to drive results while treating people with respect
  • Always provide hope for the future when delivering difficult feedback like denied promotions
  • End every meeting with three specific questions to ensure maximum forward progress

Notable Quotes

"I know this is going to be challenging for you to hear — not going to promote you — but I want you to know this. It's really important to me that you're able to succeed in your career here."

— Specific language for handling promotion denials with compassion

"They're trying to be the leader who everyone loves, but what really needs to happen is we need to drive towards results. This employee continuing to not do a great job... ultimately leads to the demise of your company."

— On why leaders must prioritize results over being liked

"Hope for the future is so important."

— On the critical ingredient when delivering difficult feedback

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