Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)

Lenny's Podcast: Product | Growth | Career

Lenny Rachitsky

Technology, Business, Entrepreneurship

5 • 1.5K Ratings

🗓️ 5 January 2025

⏱️ 84 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

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Find the transcript at: https://www.lennysnewsletter.com/p/scripts-for-difficult-conversations-alisa-cohn

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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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

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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

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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

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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.

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Transcript

Click on a timestamp to play from that location

0:00.0	I want to dive right into talking about your advice on having difficult conversations.
0:05.0	We're like in performance review season. What do you suggest when someone's being told they're not going to get the promotion?
0:10.0	Hope for the future is so important. I know this is going to be challenging for you to hear. I'm 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.
0:19.0	And so I want to continue to help you find opportunities to build your skills and to, you know, advance. You're big on
0:25.4	helping leaders understand that their job is not to make employees happy. They're trying to now
0:29.8	be the leader who everyone loves. But what really needs to happen very often is, you know, we need to
0:36.4	drive towards results. This employee continuing to not really do a great job at often is, you know, we need to drive towards results.
0:42.3	This employee continuing to not really do a great job at their job, you don't want to push them because you don't want to upset them. You don't want to give them difficult feedback, so you're just
0:45.0	going to keep hoping it works out. Ultimately, that leads to the demise of your company.
0:50.7	You have some cool advice on just how to make meetings more effective and how to especially
0:54.2	end a meeting.
0:55.2	My three questions to end the meeting are...
0:58.2	Today my guest is Alyssa Cohn.
1:02.2	Alyssa is an executive coach who has worked with C-suite execs at both startups like Etsy,
1:07.5	Wirecutter, Venmo, and Draft Kings, along with Fortune 500 companies like Microsoft,
1:12.8	Google, Pfizer, and the New York Times. She was named one of the top 50 coaches in the world by
1:17.9	Thinkers 50 and the number one startup coach for the past four years by Global Gurus. What I love about
1:23.7	Alyssa is that she gives her clients very specific and actionable advice. In her conversation, Alyssa shares specific language and phrases that you can use when having a difficult conversation with your reports to make these conversations go much smoother and be less difficult.
1:38.3	Also, three questions you should ask at the end of every meeting to make the most possible forward progress after each meeting,
1:49.0	plus why your job as a leader isn't to make people happy and what you should be focused on instead,
1:55.0	and a set of questions that she calls the founder pre-nup that you should talk through with potential founders to make sure that these are the people that you want to be working with for a long, long time.
1:59.7	There's also so much more advice. If you're a leader of people or a founder, and especially
	...

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