From linked slides it seems, that at the beginning is listening. And for that the best questions are:
1. What is X all about?
2. What I need to know to really understand X?
It also seems, that Customer Development is not about finding the perfect product hypothesis in one shot, on the contrary - the initial hypothesis is just the starting point, things you learn on the way is what matters. Just like with dancing, it will be better after some dancing, no need for over-thinking it or looking for a perfect steps. It's more about expressing yourself.
That said optimization and automation, a heuristic or even better an algorithm, that will reliably and repeatably
take some customers and output brilliant business ideas would be a nice thing to have. But it won't reduce startup risk, not massively for sure, because 'executing'
alone is more risky than 'executing on a wrong idea'.
Going back to questions.
3. What do you want?
Because sometimes the problems in given industry are very well defined and understood. And even the cliché answer "a faster horse" isn't really useless, you just have to go little further asking...
4. Why?
... a couple of times.
Next an obvious candidates will be a "profiling questions":
5. Where are time and money (and resources, attention, pain, fear...) in X?
Now, form a different angle:
6. What in X is worth spending money on?
And what is not (because of utility/price ratio)?
I have a problem with question that will filter out problems that won't make a scalable startup, maybe because scalability is property of a solution not of a problem?
It's far from complete, but above should already give some hints about what can be done.
Learn more "startup patterns" to spot more potential chances for business.
"But with smart, technically-oriented people, I'd expect there to be more sharing of real experiences, but that's often not the case."
That was a problem for me too, finally I learned that it's just like expecting them to be good at cooking. Social interaction is a skill unrelated to a technical competence and experience in particular environment affects it more than than ones intelligence.
http://www.informationisbeautiful.net/2009/how-i-learnt-to-s...
http://www.johnstonsarchive.net/nuclear/nuclearwar1.html
It may be possible if you ask "given this arsenal, how do I destroy humanity?" but that is not how wars work.