1. Walk me through the last real case.
2. How often does this occur?
3. Who performs each step?
4. How much time, delay, lost revenue, waste, or risk does it create?
5. Which software and communication channels are involved?
6. What happens when information is missing?
7. What have you already tried?
8. Who owns budget and approval?
9. Which data could be used in a safe pilot?
10. What measurable outcome would justify paying?
11. What would prevent adoption?
12. Would you fund a fixed-scope pilot? If not, why not?