Difficult Conversation Preparation

Prepare for a hard conversation at work: the opening sentence, the facts versus your story about them, the likely reactions, and the outcome you actually need.

The Prompt — replace [BRACKETS] with your details

Act as an experienced manager and coach preparing me for a difficult conversation. Be honest with me, including about my own part in it.

The situation:
- Who I am talking to and our relationship: [PERSON, ROLE, HISTORY]
- What the conversation is about: [SUBJECT]
- What has actually happened — observable facts only, no interpretation: [FACTS, WITH DATES]
- The story I am telling myself about why: [MY INTERPRETATION — be honest]
- What I have already tried or said: [PRIOR ATTEMPTS]
- What I need to be different afterwards: [THE CONCRETE OUTCOME]
- What I am worried about: [FEARS]
- Power dynamic: [ARE THEY MY MANAGER, REPORT, PEER, CLIENT]

Deliver:
1. Facts versus story: separate what happened from what I have concluded, and flag which conclusions I have not actually checked
2. What this conversation is really about, which may not be what I said it was about
3. My opening: two or three sentences that state the issue without an accusation, and without so much softening that the point disappears. Give me two versions, one direct and one warmer
4. The three most likely reactions — defensiveness, agreement then no change, an unexpected explanation — and my next line for each
5. Questions I should ask, and the one thing I should be genuinely open to hearing
6. What I am willing to compromise on and what I am not. Ask me if I have not been clear
7. My contribution to this situation, stated plainly. Do not skip this section to be nice
8. How to end: the specific agreement, who does what by when, and how we will check
9. What to do if it goes badly, and when to stop the conversation and reschedule

Do not write me a script to read. Write me preparation.

How to use this prompt

Fill in the facts field with only what a camera would have recorded. The separation from your interpretation is where the value is.
Read section 7 before the conversation and be ready to say it out loud.
Rehearse the opening only. Scripting the rest makes you a worse listener.

Why this prompt works

Hard conversations go wrong when we lead with our interpretation as if it were fact. Forcing the fact-story split before anything else is the single most useful preparation step, and pre-writing responses to the likely reactions keeps you from improvising while flooded.

Variations to try

Ask the model to role-play the other person at their most defensive so you can practise.
Add "this is a performance conversation that may lead to a formal process" and ask what to document.
After the conversation, debrief with it: what you learned and what to do next.

Common mistakes to avoid

Opening with so much cushioning that the person leaves without knowing there was a problem.
Treating your interpretation as established fact, which guarantees defensiveness.
Skipping the "my contribution" section, which is usually the part that unlocks the conversation.

Works well with

Claude

ChatGPT

Gemini

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