My Process
The first thing I do is listen. Then I ask questions — a lot of them. I need to see the whole picture before I can begin to diagnose, and diagnosis is where the real work starts. Most problems worth solving aren't what they appear to be on the surface.
Once I understand what's actually going on, I'll come back with a clear proposal: what I'd build, why, and what it gets you. Then we get to work.
How to Prepare
The one thing that makes an initial conversation most productive is a clear picture of what you're trying to solve — not the solution, just the problem. We get so used to working around broken things that we stop seeing them clearly.
So before we talk, try this: set aside how things work today and ask yourself one question: "What would this feel like if it actually worked the way it should?" Start there. Everything else follows.