Guides

How to prepare for a difficult conversation at work

Most difficult conversations go wrong in the first two minutes, and most of those two minutes can be prepared. Here is a short way to get ready, whether it's with someone on your team, a peer or your own manager.

Updated October 2, 2026

Before: two questions

  1. What do I want to be different after this conversation? Write one sentence.
  2. What does the other person care about here? Their time, their work, being heard, being treated fairly?

Tailor it to how they communicate

  • If they like detail, bring specifics and examples, and send them ahead if you can.
  • If they want the why, start with what's at stake and why it matters to both of you.
  • If they need time to think, say so: “You don't need to answer now. Let's pick this up on Thursday.”

The first two sentences

Say what you want to talk about and why, without a verdict. For example:

With someone on your team
“Sam, I want to talk about how handovers are going between us. I think we can make them easier, and I'd like your view.”
With a peer
“Priya, our last two planning meetings ended without a decision. I'd like to find a way to work through that together.”
With your manager
“I'd like to talk about how we plan my work. I want to be sure I'm putting time where you need it most.”

Sam and Priya are invented examples.

During: listen for what they ask for

  • Ask before you explain: “How does it look from your side?”
  • Notice what they ask for: details, reasons, options, or time.
  • Agree on one next step and when you'll check in.

After: follow up the way that suits them

Send a short written summary to someone who prefers writing, or a quick check-in to someone who prefers talking. Then do what you said you'd do.

Questions for your next one-on-one

  • “What's one thing I could do differently that would help you?”
  • “When I bring you something new, what's the best way to do it?”
  • “Is there anything we keep talking past each other on?”

Prepare with a read on the person

Sixen reads the work conversations you choose and notices how each person communicates: what they ask for, how they decide, and what makes them push back. You get a read on the person, the moments behind it, and two or three ways to approach them next time. You can accept, edit or reject every read, and only you see it.

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