Generic discovery questions like "what keeps you up at night" get shallow answers because prospects won't open up to strangers. Instead, come prepared with research and a strong point of view, then use active listening to summarize and confirm what they say. This approach gets better responses than vanilla questions.
Chapters
If you are consistently getting shallow answers in discovery it might be on you. Sorry, average questions they get average answers and great questions get great answers. So here's my recommendation. It's to start by scrapping these very vanilla questions from your sales Rolodex. Number one would be so what are your top two to three priorities? 2. What keeps you up at night? 3. If you had a magic wand what are the top two to three insert questions? These are what every other sales rep is being taught by enablement. They only work with prospects who are already extremely interested and they're willing to be complete open books with strangers. That is you, the sales rep. In my experience very few prospects fall into that mold from the start of a call. So the better way is to come with a prepared, strong point of view from research then actively listen, summarize and confirm. Understanding this will differentiate you from 90% plus of other sellers that they're also evaluating. Let's get it.