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My favorite question to ask investors at the end of a pitch is: "What do you suspect the reason we will fail will be?" Benefits: (1) You get *some* feedback (don't be defensive) (2) You can learn if they know something you don't (3) Counter-interview - are they smart too?
You can also do this during sales calls. They'll tell you all the objections. And you can address them. Same with interviewing for jobs "what's stopping you from hiring me right now?"
A favorite of mine when presenting a new brand project to a client is "Did we nail it or completely miss the mark?" Always gets them talking more openly about their true thoughts, and allows us to address any of the objections with our perspective on our decisions.
I also use this question a lot!
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