How to handle hard conversations at work: scripts for success

I know you’ve been there…

Your teammate gets defensive the second you give feedback.

A direct report misses the same deadlines over and over.

Your manager keeps assigning last-minute tasks that wreck your schedule.

Each of these situations has one thing in common: a hard conversation is the only way to resolve them.

That’s exactly what a reader named Cara emailed me about recently:

“How do you handle these hard conversations at work?”

Great question, Cara—because hard conversations are the price of admission for a successful career.

And yet, most of us would rather volunteer for office karaoke night than face them head-on.

The Problem

When tough topics come up, we usually pick one of two terrible options:

1️⃣ Avoid the conversation entirely (because denial feels safe)

2️⃣ Jump in without a plan (because winging it always works…right?)

Both lead to frustration, awkwardness, and zero progress.

The Big Small Thing

To answer Cara’s question, I did what any good advice-giver does:

I found the world’s best expert on hard workplace conversations.

Meet Alisa Cohn, Forbes Top 100 executive coach and author of From Start-Up to Grown-Up.

Alisa has helped leaders at Google, Microsoft, and more—so she’s basically the Yoda of delicate workplace conversations. (She’s also hilarious and in my top 7 favorite people I met in 2024.)

Lucky for us, Alisa created a free PDF called 5 Scripts for Delicate Conversations—and it’s pure gold. Download it here.​

Here are two of my favorite scripts you’ll want to use:

#1: Handling Someone’s Defensiveness

You’re giving feedback to a teammate, and they start getting defensive.

Here’s how Alisa says to handle it:

“Hey [Name], can we push the pause button? It feels to me like you’re having an emotional reaction and I just want to check in. I hope this is coming across but in case it’s not, let me be explicit and say I am only giving you this feedback to help you be the best professional you can be.

I also know it can be super uncomfortable to have these kinds of conversations—I know I often feel that way myself. That said, I think it’s important for me to tell you straight what I see so we can work together to correct it. So give me a sense of how you’re feeling and how this is coming across.”

Why it works:

• It acknowledges their emotions without invalidating them.
• It clarifies your intention (to help, not criticize).
• It creates space for them to respond without escalating the situation.

Pro tip from Alisa:

If the defensiveness doesn’t ease up, suggest revisiting the topic later with this follow-up:

“I want the best for you, and these are some topics we need to unpack. As I said, I want you to be the best professional you can be. Why don’t we both digest the discussion so far and pick it up next week?”

#2: Dealing with a Pattern of Behavior

A direct report keeps repeating the same mistake. Instead of addressing the behavior again, Alisa recommends focusing on the pattern.

Here’s her script:

“Hi [Name], I wanted to talk to you today about something I’m seeing over and over. I’ve noticed that we’ve talked a number of times about your needing to (get your report in on time; communicate key messages to your people).

Every time we talk about it you apologize and tell me you’ll fix it, and it does get better for a few weeks. But then you backslide and the same problem crops up. I don’t want to nag you—we both have better things to do.

What I need you to do is to fix this once and for all. If you need help from me, let me know. If you’d like to brainstorm tools you can use, I’m happy to do that. If you’d like to know how I handle this, I’ll share. But ultimately, I need you to take full ownership of this problem and make sure we don’t have to have this conversation again.”

Why it works:

• It addresses the pattern, not just the behavior.
• It empowers them to own the solution.
• It positions you as a coach, not a micromanager.

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How This Helps You Chase What You Want

Mastering these tough conversations isn’t just about getting through awkward moments.

It’s about becoming a leader people trust.

These scripts are just the tip of the iceberg. Alisa has 3 more scripts in her free PDF (like how to say “no” to unnecessary meetings or projects).

​You can download her free PDF here.​

Trust me, your future self will thank you.

Let’s do this,