Alisa Cohn

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Alisa Cohn is an executive coach who has worked with C-suite executives at startups like Venmo, Etsy, Wirecutter, and DraftKings, and Fortune 500 companies like Microsoft, Google, Pfizer, Dell, and IBM. Inc. Magazine named Alisa one of the top 100 leadership speakers, and she was named one of the Top 50 coaches in the world by Thinkers50 and the #1 startup coach for the past four years by Global Gurus. She is also the author of From Start-Up to Grown-Up, which won the 2022 Independent Press Award and the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name. In our conversation, we discuss:

• The psychology behind why we avoid difficult conversations

• Specific scripts for having five common difficult conversations

• How to handle defensive reactions in the moment

• The three questions you should end every meeting with

• “The founder prenup” that every founding team should work through

• Common leadership myths

• Stories of failure from Alisa’s career

Some takeaways:

1. When delivering tough feedback, use this framework:

   1. Start directly: “I want to chat with you about [specific issue]”

   2. Share observations: “What I’m hearing/seeing is [specific examples]”

   3. Connect to impact: “We both know that to be successful here...”

   4. Focus on future: “Let’s discuss how we can improve this going forward”

2. If someone gets defensive during feedback:

   1. Pause the conversation: “Let’s take a moment here”

   2. Reinforce positive intent: “I’m sharing this to help you succeed”

   3. Acknowledge emotions: “I can see this is triggering strong feelings”

   4. Offer space: “We can continue now or pause and resume later”

3. A leader’s job isn’t to make everyone happy—it’s to create conditions for success. This means:

   1. Setting clear expectations

   2. Having difficult conversations when needed

   3. Building a culture of accountability

   4. Focusing on results over popularity

   5. Creating an environment where high performers can thrive

4. End every meeting by answering three key questions:

   1. What did we decide here? (Go around the room to ensure alignment)

   2. Who needs to do what by when? (Clear action items with owners and deadlines)

   3. Who else needs to know? (Communication plan for decisions)

5. Before starting a company together, co-founders should create a “founder prenup.” This entails having hard conversations about:

   1. Personal values and how they align

   2. Vision for what success looks like

   3. How to handle conflict and disagreements

   4. Desired company culture

Where to find Alisa Cohn:

• X: https://x.com/AlisaCohn

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

• Website: https://www.alisacohn.com

• Podcast: https://www.alisacohn.com/podcast

In this episode, we cover:

(00:00) Alisa’s background

(04:48) Having difficult conversations

(12:48) Scripts for performance feedback

(20:20) How to respond when someone is defensive or upset

(25:07) Scripts for handling promotion disappointments

(31:00) Scripts for handling terminations

(35:44) The importance of positive feedback

(38:49) Understanding your job as a leader

(44:55) Recognizing your own blind spots

(49:38) Three vital questions to ask in every meeting

(55:57) The founder prenup

(01:08:24) Failure corner

(01:13:00) Final thoughts and lightning round

Referenced:

• Alisa’s free PDF downloads for Lenny’s listeners: https://www.alisacohn.com/Lenny/

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Non-Violent Communication (NVC) Model: https://www.ucop.edu/ombuds/_files/nvc-model-requesting-change-remove.pdf

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652

• How embracing emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment): https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson

• Joe Gebbia on X: https://x.com/jgebbia

• Noam Wasserman on LinkedIn: https://www.linkedin.com/in/noam-wasserman-462425

• Core Values List: https://jamesclear.com/core-values

• How Cofounders Can Prevent Their Relationship from Derailing: https://hbr.org/2022/04/how-cofounders-can-prevent-their-relationship-from-derailing

• Inside Out 2 on Disney+: https://www.disneyplus.com/movies/inside-out-2/6MeZYf9JkFii

• Ninja CREAMi: https://www.amazon.com/Ninja-NC299AMZ-Milkshakes-One-Touch-Container/dp/B09QV24FFZ

• Joseph Campbell quote: https://www.goodreads.com/quotes/136819-if-the-path-before-you-is-clear-you-re-probably-on

Recommended books:

• From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business: https://www.amazon.com/Start-Up-Grown-Up-Grow-Leadership-Business/dp/1398601403

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473

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Lenny may be an investor in the companies discussed.