Scripts for navigating difficult conversations | Alisa Cohn (executive coach) — Lenny's Podcast: Product | Career | Growth Summary

Scripts for navigating difficult conversations | Alisa Cohn (executive coach) — Lenny's Podcast: Product | Career | Growth Summary | Galaxy of Podcasts

The Conversation Breakdown

Prepare the purpose before the script

⏱ Untimed topic

Cohn asks leaders to examine what makes the conversation uncomfortable and what they hope it will improve. Avoidance can deny someone useful information about their work. The purpose is a better working relationship or performance, not venting frustration.

Practice words you can actually say

⏱ Untimed topic

She gives clients sample openings but asks them to make the wording their own. Practice turns a vague intention to give feedback into a conversation you can begin. Keep the tone neutral rather than unloading on the other person.

Build feedback around evidence and expectations

⏱ Untimed topic

Cohn's writing example names missing structure and conclusions, then points to good examples and possible help. The feedback connects observable work to the expected standard. Before giving it, ask what evidence supports your assessment rather than relying only on an impression.

Pause instead of fighting about a reaction

⏱ Untimed topic

If the exchange becomes heated, she suggests noticing the changed tone, restating why the discussion matters and checking whether to continue or pause. The conversation still needs to happen. A pause is a tool to listen and reset, not a way to evade the issue.

Deliver disappointing news clearly

⏱ Untimed topic

Her promotion example gives the decision early, explains the reasons and discusses future skill-building. Cohn urges compassion for the person hearing it. A hopeful future should not become a false promise of a later promotion or a softened account of the decision.

Make positive feedback specific too

⏱ Untimed topic

She argues that praise should be prepared with the same care as correction. Naming what worked gives people useful information and builds trust. A vague good job does less to help someone repeat the effective behavior.

Finish meetings with shared next steps

⏱ Untimed topic

Cohn ends with what was decided, who does what by when and who else needs to know. Asking people can reveal different understandings of the same meeting. Leave time for this ritual and assign follow-up so the next meeting does not simply repeat the old decisions.

Scripts for navigating difficult conversations | Alisa Cohn (executive coach)

Executive Summary (TL;DR)

Key Takeaways

Prepare the purpose before the script

Practice words you can actually say

Build feedback around evidence and expectations

Pause instead of fighting about a reaction

Deliver disappointing news clearly

Make positive feedback specific too

Finish meetings with shared next steps

The Conversation Breakdown

Prepare the purpose before the script

Practice words you can actually say

Build feedback around evidence and expectations

Pause instead of fighting about a reaction

Deliver disappointing news clearly

Make positive feedback specific too

Finish meetings with shared next steps

Core Frameworks & Ideas

Evidence-based feedback

Pause and reset

Three-question meeting close

Actionable Next Steps

Notable Quotes

The One Thing to Remember