This is an interesting technique that comes in handy in a surprising number of venues - dealing with contractors, doctors, job interviews (both giving and receiving), purchasing complicated/expensive items, travel, restaurants, hotels etc.

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You’re in a situation where you are well prepared, perhaps even with a list of questions prepared in advance. You’ve gotten the answers you were seeking, which may or may be what you have hoped. It’s the moment of truth, you have to either end the conversation, seal the deal, walk out, whatever the case may be. However, there’s a part of you that feels like something important has been left unsaid, but you don’t know how to identify it.

Try this technique. It doesn’t work all the time, but it often yield some answer and perhaps an interesting line of discussion that certainly would have been overlooked otherwise.

What question should I be asking that I don’t know I should ask?

Or the variations,

What question should I be asking you right now that I’m forgetting to ask?

What questions would you be typically asked at this point?

What question would you ask if you were in my position right now?

They are all pretty similar, and will often yield a novel response and an option that might not have been so obvious. It’s not magic - if a person doesn’t want to share anything new with you it’s game over. But if there’s a reason why the person might have been just a little less forthcoming than they should, this might be enough to let their better nature take over and tell you something you didn’t expect.

I’ve had good luck with it, and it’s free. Try it!
I’d like to hear about your surprising responses. Let me know in the comments below.