Lenny’s Podcast · Podcast episode · Communication & influence · Leadership & management

Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more

Lenny Rachitskywith Alisa CohnJan 5, 2025115 min▶ 17K
SourceLenny’s Podcast
KindPodcast episode
PublishedJan 5, 2025
Readers▶ 17K
Originalyoutube.com ↗
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Alisa Cohn is an executive coach who has worked with C-suite leaders at startups and Fortune 500 companies, and was named a top startup coach by Global Gurus. In this conversation with Lenny Rachitsky she walks through practical scripts for hard conversations, including performance feedback, handling defensiveness, promotion denials, and firing, plus tools for running effective meetings and aligning co-founders.

01Key learnings

  • Before a hard conversation, identify what you're making it mean (e.g., fear of upsetting someone) and check your intent: the aim is to help the person grow, not to hurt them.
  • Frame performance feedback around observable facts and expectations, citing what you've heard from multiple people, and keep your tone neutral and matter-of-fact rather than emotional.
  • Build the relationship with positive, specific feedback regularly so people hear criticism as coming from someone who wants to help them, not someone who dislikes them.
  • If someone gets defensive or emotional, pause the conversation, remind them why it matters to their career, and offer to continue later instead of arguing.
  • When denying a promotion, deliver the news early, explain the reasons, and paint a path forward so the person keeps hope for the future.
  • Before firing someone, make sure they have already had clear, documented conversations with a concrete deadline; involve HR or legal and keep the termination itself brief.
  • End every meeting by asking what was decided, who needs to do what by when, and who else needs to know, and capture the answers as deliverables to avoid re-deciding.
  • Co-founders should discuss values, vision of success, conflict handling, decision-making when they disagree, and culture before starting, since conflict is a major cause of startup failure.
“Hope for the future is so important.”Alisa Cohn · Lenny’s Podcast · 00:00:10
“Ultimately, that leads to the demise of your company.”Alisa Cohn · Lenny’s Podcast · 00:00:29
“My three questions to end the meeting are, what did we decide here? Who needs to do what by when? And who else needs to…”Alisa Cohn · Lenny’s Podcast · 00:50:03

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.