Guide · stress · 3 min read

Preparing for a conversation you are dreading, without the usual advice, if you are new to this

Most dread is about the first thirty seconds, not the conversation. Prepare for those and the rest gets easier.

Start here

A short explanation first, because knowing why makes the doing easier.

Nothing here assumes you have done this before.

If you only do one thing from this page, do the first point below. It is first because it removes the most friction for the least effort.

What helps

Pick a time when neither of you is hungry, tired or about to leave. Timing prevents more bad conversations than phrasing does.

Decide in advance what you will do if it goes badly. Having an exit plan makes it less likely you will need one.

Do four slow breaths before you start. Not to calm down — to give yourself a beginning.

What to do when it does not work

Plan one question you genuinely want answered. It turns a speech into a conversation.

Write the first two sentences you will say. Not a script for the whole thing — just the opening, because that is where people freeze.

Decide what you want to happen, not just what you want to say. Those are different, and the second one often gets in the way of the first.

A note on effort

Start with what's physical. Everything else can wait.

Questions people ask

Should I write it down and read it?

For the opening, sometimes. Beyond that, reading a script usually makes people sound less like themselves.

Written for people who want the practical version. No accounts, no tracking, no newsletter wall.