Human Creative Coaching
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Hard Conversation Prep · free

The conversation you keep putting off.

Ten short steps, about eight minutes. You will leave with a plan, and very likely a clearer sense of what you actually want from this conversation.

Nothing you write leaves your browser unless you choose to email it to yourself.

Example
OpenI want this partnership to work for both of us.
The one sentenceThe last three launch dates slipped, and I found out the day before each time.
What I am askingTell me as soon as a date moves, no later than a week out.
Check backTomorrow morning. A short text.
About this tool

How to prepare a hard conversation

Most hard conversations do not go badly. They do not happen at all. This free tool walks you through the eight moves I use with founders, executives and artists before a conversation they have been avoiding: start on their side, say the problem in one sentence, hear them and come back, own your part, ask for one specific change, name a consequence only if it is needed, end on their side, and check back within a day.

It takes about eight minutes, or two if that is all you have. You leave with a plan you can keep, a few replies to practice against, and a time to follow up. Everything you write stays in your browser. The moves are explained in full in 8 Elements of Relational Confrontation, and what keeps most of us from starting is in 3 Obstacles to Confrontation.

How do I start a conversation I have been avoiding?

Begin by saying what you want for the other person and for the relationship, then name the problem in one sentence of fact. The opening tone tends to shape everything after it.

What if they get angry or change the subject?

Expect it, and plan for it. Hear them out, then come back to the one thing you came to talk about. The tool helps you write that sentence before you need it.

Can I ask them to apologize?

You can hope for an apology, but it cannot be asked into being. Ask for an action you could both see happen. A sincere apology often follows that.

What if the conversation goes badly?

One conversation rarely settles something that took months to build. Let it cool before you decide what it means, and plan a second round. If you would rather not do that alone, start a conversation with me.

Is this therapy or legal advice?

No. It is a coaching tool. If you are afraid for your safety, talk to someone you trust or visit thehotline.org. If money, equity or contracts are involved, talk to an attorney first.