Walk me through the last time this problem happened to you.
What did you do about it? What did you try before that?
How often does this come up in a typical week?
If you could wave a magic wand, what would happen?
What have you tried that didn't work — and why?
How are you solving this today? What does that cost you (time or money)?
Who else on your team feels this?
If a tool solved this perfectly, what would you stop doing?
Would you pay for that? What would it be worth to you monthly?
Is there anyone else I should talk to?