Warm-Up & Context Setting

"Hey [First Name], thanks for making time. I’m diving deep into [problem space] to understand what’s working and what’s broken. No pitch, just a real conversation to learn from your experience.

Can you share a bit about your role and how [problem] fits into your work?"

→ Follow-ups:

• How often do you deal with [problem]?

• What’s the most frustrating part of that process?

Understanding the Problem

"Can you walk me through the last time you dealt with [problem]? What triggered it, and how did you approach solving it?"

→ Follow-ups:

• How long did it take from start to finish?

• What was the hardest part?

• Did it impact your time, budget, or workflow?

Existing Solutions & Gaps

"What tools, workarounds, or services are you using now to handle this?"

→ Follow-ups:

• What do you like or dislike about the current solution?

• Have you looked for alternatives? Why or why not?

• If you could fix one thing, what would it be?

Decision-Making & Prioritization

"If a better solution existed, what would make you switch?"

→ Follow-ups:

• What’s a dealbreaker vs. a nice-to-have?

• What factors influence your decision to adopt something new?

• Have you tried something new that didn’t work? What happened?

Wrap-Up & Next Steps

"This has been insanely helpful. If we build something that truly solves this, would you be open to a follow-up?"

→ Follow-ups:

• Is there anyone else I should talk to?

• What’s the best way to keep you in the loop?