Skill library / Claude

Difficult Conversation Prep skill for Claude

Difficult conversations go wrong when we either avoid them or walk in without a clear aim and say too much, too bluntly or too vaguely. This skill gets Claude to ask the right questions first, then build a short plan with your opening lines, likely reactions and a practice run you can rehearse against.

Customise this skill free

What it's good for

Telling a team member that their work has dropped below standard, without it turning into an argument
Asking your manager for a pay rise or a change to your hours and wanting to be ready for a no
Telling a long-standing client that a deadline will be missed or a price is going up

How the skill works

Ask me, one or two questions at a time, who the conversation is with, what has happened, what I want to come out of it, and what I am most worried about. Do not draft anything until I have answered.
Summarise the situation back to me in three or four plain sentences, separating facts I can evidence from my assumptions or interpretations. Ask me to correct anything wrong.
Write a one-page plan: my main aim, one thing I must not lose sight of, a calm opening of two or three sentences, the key points in a sensible order, and a clear ask or next step to close.
List the three or four most likely reactions (for example defensiveness, upset, pushing back or silence) and give a short, respectful reply I could use for each.
Offer to role-play the other person so I can practise. If I accept, stay in character and keep to one realistic reaction at a time. When I say stop, give me honest feedback on what worked and what to tighten.

Built-in rules

Stick to facts and specific examples. Do not help me guess at the other person's motives or personality, and flag it when I start to.
Keep the tone firm but fair. Do not write scripts that are manipulative, passive-aggressive or designed to corner the other person.
If the situation involves possible discrimination, harassment, disciplinary action or dismissal, say clearly that I should check my HR policy or get proper advice (such as from Acas) before going ahead.

Example

You: “I need to tell one of my team, Sam, that his reports have been late three times this month and it's affecting other people. He's usually great and I don't want to damage things. Can you help me prep?”
Result: Claude asks a few questions about the late reports and what you want from Sam, then gives you a one-page plan with a kind but direct opening, three points with dates, a clear ask, and replies for if Sam gets defensive or says he is overloaded.

SKILL.md template

Save as difficult-conversation-prep/SKILL.md.

---
name: difficult-conversation-prep
description: "Helps you plan a tricky workplace conversation, such as critical feedback, a performance concern, a pay rise request or bad news for a client. Use it when you're dreading a chat and want a clear aim, opening words, likely reactions and calm replies ready."
---

# Difficult Conversation Prep

## Workflow
1. Ask me, one or two questions at a time, who the conversation is with, what has happened, what I want to come out of it, and what I am most worried about. Do not draft anything until I have answered.
2. Summarise the situation back to me in three or four plain sentences, separating facts I can evidence from my assumptions or interpretations. Ask me to correct anything wrong.
3. Write a one-page plan: my main aim, one thing I must not lose sight of, a calm opening of two or three sentences, the key points in a sensible order, and a clear ask or next step to close.
4. List the three or four most likely reactions (for example defensiveness, upset, pushing back or silence) and give a short, respectful reply I could use for each.
5. Offer to role-play the other person so I can practise. If I accept, stay in character and keep to one realistic reaction at a time. When I say stop, give me honest feedback on what worked and what to tighten.

## Rules
- Stick to facts and specific examples. Do not help me guess at the other person's motives or personality, and flag it when I start to.
- Keep the tone firm but fair. Do not write scripts that are manipulative, passive-aggressive or designed to corner the other person.
- If the situation involves possible discrimination, harassment, disciplinary action or dismissal, say clearly that I should check my HR policy or get proper advice (such as from Acas) before going ahead.

How to install in Claude

Make your version below to get the skill file (keep the zip as it is). In Claude, go to Settings, then Capabilities, and switch on "Code execution and file creation". Works on every plan, including Free. Go to Customize, then Skills. Tap +, then Create skill, then Upload a skill, and choose the zip. Then just ask Claude for help as normal.

Pro tip

Create a Claude Project called Difficult Conversations and paste this skill into its instructions so every new chat starts with the same questions. Use initials or job titles instead of full names and leave out anything confidential, then ask Claude to role-play the other person in the same chat.

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FAQ

How do I install the difficult conversation prep skill in Claude?

Is it free?

Yes. You can copy this template, or generate a customised version free (5 per day, no login).

Does it work on other platforms?

Yes. The template works as plain instructions in any AI. When you make your own version, we show the setup steps for whichever AI you use, with a Copy button.