Something to doWorking with others
Have the conversation you've been avoiding
A simple exercise to prepare for a hard conversation, so you can open it with curiosity instead of a verdict
Why it’s worth your time
Conversations we avoid tend to grow in our heads until they feel too big to start. Writing the facts down separately from the story you've built around them shows you how much of your frustration rests on a guess. Opening with what you saw and a real question, rather than your conclusion, leaves the other person room to fill in what you don't know.
How to prepare for a difficult conversation
You’ll come away with a clear opening line and the one thing you're asking for.
We’ll turn this into a checklist you can tick off.
- Write down the facts, the story, and your ask.
Keep each answer short. The point is to see the facts and the story side by side, on the page rather than in your head.
Stays in this browser only. Nobody else sees it.
- Look hard at the story.
Read it next to the facts. How much of it did you see, and how much did you fill in? Could one of the other explanations be true?
Tip: Being honest with yourself here is most of the work. If your own part shows up in the facts, put it in your opening.
- Pick a time and ask for it.
Private, unhurried, and not straight after the latest incident. A walk or a quiet call can feel less like a summons than a meeting invite with a vague title.
You“Could we find some time this week? There's something I'd like to talk through properly rather than in passing.” - Open with a fact and a question.
Use the opening you wrote. Then listen until you understand their side, even if it takes longer than you planned.
Tip: If you catch yourself trying to win, go back to what you said you really want.
- Make your ask, and agree what's next.
Say the one thing you'd like to change, plainly. Then ask what they'd need to make it work, and what they'd like from you in return.
Good moments for this: when something has waited more than a weekbefore any conversation that feels high stakeswhen you catch yourself rehearsing arguments
We’ll turn this into a checklist you can tick off.
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Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
They almost certainly have their own version of events, possibly with you in a role you wouldn't recognize. Expect it, and treat hearing it as progress.
What might make this harder
Pause it. Say you want to get this right and suggest picking it up tomorrow. Stopping is better than saying something you'll have to repair.
Questions people ask
How do you start a difficult conversation at work?
Open with one specific fact and a genuine question about it, rather than your conclusion. For example: my analysis went out without my name on it in the last two updates; I wanted to ask how that came about.
How do I prepare for a hard conversation with a coworker?
Write down what happened, the story you've told yourself about it, other explanations that fit, what you really want, and one specific ask. Then plan your first two sentences.
What is Crucial Conversations about?
It's a book by Kerry Patterson, Joseph Grenny, Ron McMillan and Al Switzler on talking when stakes are high, emotions run strong, and opinions differ. A central idea is separating the facts from the stories we tell ourselves about them.
Why this works, and where it comes from
Most people who've been avoiding a conversation have already had it many times, in their heads. Each rehearsal adds a little evidence and settles them a little more firmly on what the other person is like. By the time most people finally speak, they arrive with a verdict, and the other person can hear it in the first sentence. From there, the conversation is about defending themselves rather than fixing anything.
The book Crucial Conversations, by Kerry Patterson, Joseph Grenny, Ron McMillan and Al Switzler, draws a line that sits at the heart of this: between what you actually saw and heard, and the story you told yourself about it. Stories arrive fast and feel exactly like facts. The authors suggest starting a hard conversation from the facts, since they're the least likely part to provoke. Writing the two down separately is a simple way to see which is which before you say anything.
The book also asks you to decide what you really want, for yourself, for them, and for the relationship. Without that, it's easy to drift into trying to win, which feels good for about a minute. And it's worth remembering that the other person may simply not know. People can change a surprising amount about their working lives by saying what they need, and the colleague who never heard it never had the chance to help.
If it involves harassment, discrimination, or you feel unsafe, don't prepare for it alone; go to HR or your manager. A small, one-off thing may need only a quick, casual word, since half an hour of preparation can make something minor feel major.
Other simple things to consider
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Written by Truest, based on Crucial Conversations: Tools for Talking When Stakes Are High (Kerry Patterson, Joseph Grenny, Ron McMillan, Al Switzler). Last updated October 2, 2026. We sell a career membership; where that’s relevant above, we say so.