Jack Thompson

Prepare for a Difficult Conversation Without Scripting It

Prepare for a hard talk with a report, peer or manager: separate facts from your story, open well, anticipate reactions and leave with a clear next step.

At a glance

Best for: Managers, peers and employees preparing for feedback, performance, boundary or conflict conversations they have been putting off.
Tested on: Claude · Opus 5.5
You fill in: personissuegoalworry
You get: Purpose Find out what's changed for Sam, and agree a realistic plan for the next few weeks so review times and quality recover without him feeling… (full result below)

career

personal-growth

meetings

Prompt

Help me prepare for a difficult conversation. I want to walk in clear, not holding a script.

Who, and our relationship: {{person}}
The issue, with specific facts (what happened, when): {{issue}}
What I want to come out of it: {{goal}}
What I'm worried will happen: {{worry}}

Output:

1. Purpose in one sentence: what a good outcome is for both of us.

1. Facts vs. my story: split what I've written into observable facts and my interpretations or assumptions.

1. Their side: the most generous plausible explanation of their behavior, in their voice.

1. Opening: two sentences, under 40 words total. Name the topic, give one fact, then ask a question. Don't use "we need to talk", don't start with praise and don't open with "you always".

1. Likely reactions: 3 reactions they might have, each with a calm response of one or two sentences.

1. Don'ts: 3 things to avoid, specific to this situation.

1. Close: how to end with an agreed next step and a check-in date.

Flag anything in my notes that I shouldn't raise, such as secondhand information or things outside my role.

Fill in

{{person}}: Who you're talking to and the relationship.e.g. Sam, senior engineer on my team, reports to me, 3 years
{{issue}}: Specific facts: what, when, how often.e.g. Missed review SLA on 6 of 9 PRs in September; 2 bugs shipped...
{{goal}}: What you want from the conversation.e.g. Understand what's going on and agree a plan
{{worry}}: What you fear will happen.e.g. He gets defensive, or I pry into his family

Example input

person: Sam, a senior engineer on my team. He reports to me and has been here 3 years. He's normally one of our most reliable people.

issue: In September he missed our 24-hour code review turnaround on 6 of the 9 PRs he was assigned. Two features he shipped (the CSV export on 4 Sep and the team-invites flow on 17 Sep) had bugs that reached customers. He's been quieter in standups. A colleague mentioned in passing that Sam's father is ill; Sam hasn't told me himself.

goal: Understand what's going on, agree something practical for the next few weeks, and make sure he knows I'm on his side, while being clear the quality issue is real.

worry: That he gets defensive and shuts down, or that I end up prying into his family situation when he hasn't chosen to tell me.

1720

Generated Outputs (1)

3 hours ago

Claude

Opus 5.5

3 hours ago

Generated Output

1. Purpose
Find out what's changed for Sam, and agree a realistic plan for the next few weeks so review times and quality recover without him feeling cornered.

2. Facts vs. my story

• Facts: 6 of 9 September reviews missed the 24-hour turnaround. Bugs reached customers from the CSV export (4 Sep) and team invites (17 Sep). He's spoken less in standups. He has three years of reliable work.

• Story: "something is going on", "he's distracted", and anything linking this to his father. That last one is secondhand and unconfirmed.

3. His side (generous version)
"I've had a lot on and I've been trying to keep up without making it everyone's problem. I know a couple of things slipped. I didn't want to use it as an excuse."

4. Opening
"I wanted to talk about September. Reviews have been slower and a couple of bugs got through, which isn't like you. How's it been from your side?"

5. Likely reactions

• Defensive ("the specs for invites were unclear"): "That may be part of it, and let's fix it. I'm less worried about blame than about what would make the next few weeks easier."

• Shuts down ("it's fine, I'll sort it"): "I believe you will. I'd still like to take something off your plate, not just ask for more. What would help?"

• Opens up about something personal: listen, don't problem-solve. Then: "Thank you for telling me. Let's work out what flexibility would help. That matters more than the review queue right now."

6. Don'ts

• Don't mention his father. It's secondhand. If he raises it, respond then; if not, it isn't yours to bring up.

• Don't say "you've seemed checked out". It's an interpretation, and it will land as an accusation.

• Don't let a kind conversation end without an actual change, or the quality issue quietly continues.

7. Close
Agree one or two concrete changes. For example: temporarily cut his review load to 5 a week, or pair on the next feature's test plan. Then say: "Let's check in on Friday the 9th and see how it's going." Send him a two-line recap afterwards so he knows exactly what you agreed.

Flag: the colleague's comment about his father should stay out of the conversation and out of any written notes.

Why it works

Separating facts from your story is the core move. "Missed 6 of 9 reviews" is discussable, while "he's checked out" starts a fight. The generous explanation in their voice makes you rehearse empathy before you're in the room, which lowers the temperature more than any phrasing trick.

The opening constraints (under 40 words, a fact, then a question, with banned openers) stop the two classic failures: the praise sandwich and the ambush. Preparing three reactions means a defensive reply doesn't knock you off course. The final flag, about secondhand information and things outside your role, catches the mistakes that damage trust permanently.

When not to use it

Not for situations involving harassment, discrimination, safety or possible legal action. Involve HR or a professional and follow your company's process. If the conversation is formal (a written warning or performance plan), your HR team's wording matters more than this. And prepare, don't memorize: reading lines aloud in the meeting will feel scripted to the other person.

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