Scripts for navigating difficult conversations | Alisa Cohn (executive coach)
Lenny Rachitsky (host), Alisa Cohn (guest), Narrator
In this episode of Lenny's Podcast, featuring Lenny Rachitsky and Alisa Cohn, Scripts for navigating difficult conversations | Alisa Cohn (executive coach) explores scripts and mindsets to master tough conversations and effective leadership Executive coach Alisa Cohn walks through specific scripts and mental models for handling difficult conversations at work, including performance feedback, promotions, and firing. She emphasizes that leaders must prioritize results and growth over short-term harmony, and that withholding feedback ultimately harms both people and companies.
Scripts and mindsets to master tough conversations and effective leadership
Executive coach Alisa Cohn walks through specific scripts and mental models for handling difficult conversations at work, including performance feedback, promotions, and firing. She emphasizes that leaders must prioritize results and growth over short-term harmony, and that withholding feedback ultimately harms both people and companies.
Cohn shares word-for-word examples for giving clear, evidence-based feedback, addressing defensiveness, delivering bad news about promotions, and setting up ‘last chance’ conversations before termination. She also offers practical tools for running better meetings, aligning co-founders via a “founder prenup,” and using personal operating manuals to improve collaboration.
Throughout, she reframes hard conversations as acts of service that create clarity, trust, and long-term opportunity—even when they trigger short-term discomfort.
Key Takeaways
Treat difficult conversations as acts of service, not cruelty.
Avoiding hard feedback feels kind in the moment but deprives people of the chance to improve and often leads to bigger problems later; your intent should be to help them grow and succeed, not to vent or punish.
Get the full analysis with uListen AI
Anchor feedback in observable facts and clear expectations.
Use language like “what I’m hearing” or “what I’ve observed” and tie it to role expectations and team impact, instead of vague judgments; this makes conversations less personal, more fair, and easier to hear.
Get the full analysis with uListen AI
Prepare for defensiveness and emotion instead of reacting to it.
When someone gets upset or defensive, pause the conversation, restate your positive intent (“I’m telling you this to help your career”), and offer to continue later if needed, rather than arguing or backing off entirely.
Get the full analysis with uListen AI
Be direct and hopeful when denying promotions or firing.
Don’t bury the lead—state the decision clearly, explain the rationale, and then paint a credible path forward (skills to build, kinds of leaders they’ll work with, or support in transition) to preserve dignity and motivation.
Get the full analysis with uListen AI
Leaders’ primary job is driving results and building winning cultures, not keeping everyone happy.
Over-indexing on short-term happiness—avoiding feedback, tolerating underperformance, over-investing in perks—erodes performance and culture; clear expectations, accountability, and celebration of wins create deeper engagement.
Get the full analysis with uListen AI
End every important meeting with three simple questions.
Ask: (1) What did we decide here? ...
Get the full analysis with uListen AI
Invest early in alignment with co-founders and colleagues.
Use tools like a “founder prenup” (values, vision, conflict style, decision rules, culture) and personal operating manuals (communication preferences, pet peeves, delegation style) so misalignments surface early, before they become existential.
Get the full analysis with uListen AI
Notable Quotes
“If you don’t give them the opportunity to hear what you have to say, you’ll never have the opportunity to help them improve or change the relationship.”
— Alisa Cohn
“Hope for the future is so important.”
— Alisa Cohn
“It’s very misguided for leaders to think their most important role is to keep people happy.”
— Alisa Cohn
“You have to pick yourself up from the ground and pull yourself forward; when you keep taking action, you’ll get where you need to go.”
— Alisa Cohn
“Sometimes you need to have patience and sometimes you need to look at the process—your job as a leader is to know the difference.”
— Alisa Cohn
Questions Answered in This Episode
How can I adapt Alisa’s scripts to sound authentic in my own voice while preserving their structure and intent?
Executive coach Alisa Cohn walks through specific scripts and mental models for handling difficult conversations at work, including performance feedback, promotions, and firing. ...
Get the full analysis with uListen AI
Where in my team or company am I avoiding a hard conversation that, if handled well, could unlock significant growth or trust?
Cohn shares word-for-word examples for giving clear, evidence-based feedback, addressing defensiveness, delivering bad news about promotions, and setting up ‘last chance’ conversations before termination. ...
Get the full analysis with uListen AI
What evidence do I actually have for my performance judgments about people, and how might those judgments change if I forced myself to list observable facts?
Throughout, she reframes hard conversations as acts of service that create clarity, trust, and long-term opportunity—even when they trigger short-term discomfort.
Get the full analysis with uListen AI
To what extent am I optimizing my leadership for short-term harmony versus long-term results and a winning culture?
Get the full analysis with uListen AI
If I’m a founder or senior leader, have I truly aligned with my co-founder(s) on values, vision, and conflict resolution—or am I relying on assumptions that could later blow up?
Get the full analysis with uListen AI
Transcript Preview
I want to dive right into talking about your advice on having difficult conversations, or like in performance review season. What do you suggest when someone's being told they're not going to get the promotion?
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, and so I want to continue to help you find opportunities to build your skills, and to, you know, advance.
You're big on helping leaders understand that their job is not to make employees happy.
They're trying to, like, be the leader who everyone loves. But what really needs to happen very often is, you know, we need to drive towards results. 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 going to keep hoping it works out. Ultimately, that leads to the demise of your company.
You have some cool advice on just how to make meetings more effective, and how to especially end a meeting.
My three questions to end the meeting are...
(instrumental music) Today my guest is Elissa Cohn. Elissa is an executive coach who has worked with C-suite execs at both startups, like Etsy, Wirecutter, Venmo, and DraftKings, along with Fortune 500 companies like Microsoft, Google, Pfizer, and the New York Times. She was named one of the top 50 coaches in the world by Thinkers 50, and the number one startup coach for the past four years by Global Gurus. What I love about Elissa is that she gives her clients very specific and actionable advice. In our conversation, Elissa 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, also three questions you should ask at the end of every meeting to make the most possible forward progress after each meeting, plus why your job as a leader isn't to make people happy and what you should be focused on instead, and a set of questions that she calls the founder prenup 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. There's also so much more advice. If you're a leader of people or a founder, and especially if you dread hard conversations, this episode is for you. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Elissa Cohn. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out of the box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. This episode is brought to you by Rippling, a single platform to build and scale your startup on. Rippling handles all the can't get it wrong admin work of payroll and benefits, giving you back hours every week, but it does a lot more than that. Rippling is a game changer for the entire company, with tools for HR, IT, and spend, all built from the ground up and designed to work together seamlessly. Just hired someone? Rippling makes onboarding easy, whether your new hire is sitting next to you or halfway across the world. In just a few clicks, Rippling automatically generates an offer letter, ships a laptop with the necessary apps and permissions, and even delivers a corporate card. An employee needs to update their benefits contribution? When they do it in Rippling, the change automatically syncs to payroll. CTO forgot her laptop in an Uber? Lock it remotely with Rippling. Many startups I've invested in, like Sprig, Ele.me, and ClassDojo use Rippling because it's a force multiplier for lean teams, helping them eliminate major headaches and operate their business more efficiently. For a limited time, Rippling is giving Lenny's listeners three months off. To redeem, visit rippling.com/lenny. That's rippling.com/lenny. Elissa, thank you so much for being here and welcome to the podcast.
Install uListen to search the full transcript and get AI-powered insights
Get Full TranscriptGet more from every podcast
AI summaries, searchable transcripts, and fact-checking. Free forever.
Add to Chrome