Preparing for a hard meeting in an hour

I am keeping the details out of this one, because they are not mine to share. The method is the useful part.

I disagreed with another office about how a written policy should be read. I had the policy in front of me, and I thought the text supported my reading. I had a meeting within the hour.

What I asked

I did not ask "am I right?" I asked: what will the other side say, and in what order?

What came back

A ranked list of the arguments I was likely to hear, each with the strongest version of it. Some of them were good arguments. A few I had not considered at all:

• Questions about what a key word in the policy actually means.
• Practical concerns about coverage on a small team.
• The worry about precedent: if this is allowed here, who asks next?
• The mechanics of making it work in the systems we already use.

Then three pieces of advice:

• Bring a plan that answers the practical concern before anyone raises it.
• Know one specific fact cold before walking in, because the whole question could turn on it.
• Close by asking which written provision supports the other reading.

That last one is a question, not an argument. It keeps the conversation on the text.

What I take from this

Before the meeting, I had also drafted three emails with Claude's help: a detailed one, a softer one, and a short note asking to talk in person. The short note mattered most to me. I would rather settle things at the lowest level, face to face, than win an email thread.

The point of the preparation is not to be more combative. When you have already heard the other side's best points, you can listen when they make them.

Where it falls short

It only knows the documents you show it. It cannot tell you about the history between two offices or what was said in a hallway. And it should never be the one deciding. It helps you think. You go to the meeting.

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Part of the series 27 ways I actually use AI. Claude drafted this post from the record of our work together.