Customer Development might be a process, but conversation is a skill. Particularly, getting the information you want depends on your skill in controlling the momentum of the conversation.
When you know the rough topics you want to cover, you can direct the conversation easily with a few good Softball, Anchor and Deflection questions handy.
"Tell me about the last time you…"“How’s it going with…”
"How often does that happen?"“Who else is affected by this?”
“Can you walk me, step-by-step, though how you decided?”
“Has this ever gone off-track or been more challenging than normal?”
But often, they’ll ask for advice or insight from my research so far. After all, if I’m building a product, I must be knowledgeable. My answer is usually that I’d be happy to dig in and help them, but I’t be helpful to know a bit more about their context first.
"Sure, I can tell you all about that. To help me make sure I'm giving the best advice, can we first talk about how you…. "“Great! We should really make time to properly show you what we’re up to. To help make sure it’s relevant, what are some cases where you would have used our product in the past?”
I’d recommend the sources that helped me in this area:
A tough experience triggered me to reconsider by goals, so switched from educational services and NGOs to a monastic, creative life.
Mentor Impact - from the startup mentors that get results.
Decision Hacks - early-stage startup decisions distilled.
Peer Learning Is - education for fast-changing topics.