Rules: Ask about their past, not hypotheticals ("what did you do last time?"). Don't pitch first — the moment you do, they get polite and the data dies. Listen ~80%. Write their exact words.
Warm-up — their world
- Walk me through how you find your next engagement. What's the very first thing you do?
- Last time you went after a client, what did you have to create / prepare? (résumé? capability statement? proposal? bio? deck? nothing?)
Find the pain
- What part of winning new work is most annoying or time-consuming? Why that part?
- Last time you built a doc to win a client — from scratch, template, or copy-paste? How long did it take?
- Tell me about a time you lost an engagement you wanted. What made the difference?
Money — what they already pay for
- What tools/services do you pay for to win or manage work? Roughly how much a month?
- Ever paid a writer / designer / coach for proposals, positioning, or pitch help? What did it cost?
Test the wedge (still no pitching)
- When you send a prospect something to show what you do — what is it? Last updated when? Happy with it?
- Wave a wand: one part of getting new clients done for you — what would it be?
Only now — lightly test the solution
- (Only if they named a relevant pain:) I'm building something that creates consultants' pitch docs — capability statements, proposals — from a quick conversation, in their own words/facts. Help, "meh," or solves a real headache? WHY? (the "why" is the whole answer)