Free conversation planner

A little preparation.
A clearer conversation.

For the conversation you’ve been putting off. Find your opening, choose one request, and prepare for a difficult reply.

Try a fictional conversation before writing your own plan.

Your three-part worksheet

You can use these prompts on paper or in your notes. Enable JavaScript for the interactive planner.

  1. Opening: What happened, and what do you want to talk about?
  2. Request: What is one concrete next step you can ask for or offer?
  3. Follow-up: If the reply is difficult, how can you acknowledge it, stay with your request, or pause?

Example: “Can we talk about overnight guests? I need quieter evenings before early shifts. Could we check with each other first?” If the reply is “It’s my home too,” a follow-up could be: “I want us both to feel at home. What arrangement would work for you?”

How to plan a difficult conversation

You don’t need a perfect script. A short plan can give you a place to begin and something to return to when the conversation goes off track.

  1. Start with something specific. Describe the situation you want to discuss. “There have been guests staying over three nights this week” gives you more to work with than “You’re inconsiderate.”
  2. Give the conversation one job. Ask for a clear change, acknowledge a mistake, or arrange a time to talk. Leave room for the other person to answer.
  3. Prepare to listen, or pause. Your follow-up can acknowledge disagreement without giving up your request. You can also say you need time and suggest when to continue.

The examples here are writing exercises, not predictions of how someone will respond. For a fuller example, read how to practice a difficult conversation. If you’re planning a message, try the text rehearsal guide.

What happens to my writing?

The planner assembles the text in your browser. It doesn’t send your writing to Pretake, an AI service, analytics, or the person you’re preparing to talk to. Copy or print it if you want to keep it. The share button shares only the blank planner’s link.

The website uses basic visit and button-click analytics, without your worksheet text. The iPhone app processes chat text differently; read Pretake’s data-handling details before importing a conversation.