Hard Conversations
Apologies, saying no, setting boundaries, ending things and giving tough feedback, in your voice and without making it worse.
Good for: anyone rewriting the same difficult text for the tenth time
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- Download page plus a copy emailed to you
- Plain-text file and a print-ready version
- Works in ChatGPT, Claude or Gemini
What's inside
- Write a real apology Owns it, no 'but', and says what changes.
- Say no without over-explaining Kind, short and final.
- Set a boundary with family Clear line, clear consequence, no lecture.
- Give tough feedback to someone you manage Specific, fair and focused on what's next.
- Respond to criticism without getting defensive Take what's fair, push back on what isn't.
- End a relationship or friendship kindly Honest, brief and not cruel.
- Ask for money you're owed from a friend Direct, friendly and specific about amount and date.
- Talk to a roommate or neighbor about a problem Fix the issue, keep the peace.
- Share bad news at work Lead with the news, then the plan.
- Plan what to say before a hard talk Your goal, your first line and your exit line.
What a finished result looks like
Chris, I'm sorry I missed your birthday dinner on Saturday and didn't tell you until the next day. You'd planned it for weeks, and I left an empty seat and no explanation. That wasn't fair to you.
From now on, if I can't make something, I'll tell you as soon as I know, not after. I'd like to take you to dinner this week, my treat, if you're up for it.
Example output from the free sample prompt, run in Claude with invented details. Your results will use your details and can differ.
Free sample: Write a real apology
You are a communication coach who helps people apologize well. Who I'm apologizing to: [PERSON, RELATIONSHIP] What I did: [WHAT HAPPENED, HONESTLY] How it affected them: [THE IMPACT] What I'll do differently: [THE CHANGE] How I'll send it: [TEXT, EMAIL, IN PERSON] Your task: write my apology. Rules: - MUST name what I did in plain words and acknowledge the impact. - MUST include what I'll do differently. - NEVER use 'but', 'if you were hurt', or explain my intentions before owning it. - If anything is missing, ask me up to 3 short questions first. Give me: the apology sized for how I'm sending it, and one line on what not to add.