I liked a lot this article by Josh Bernoff, about " The power of not understanding": here it goes.
"When I started at Forrester, a huge intellectual presence towered over the research organization. This was Bill Bluestein, who rose to be come president of the company and inspired us all, until he died (far too young) in 2001.
Bill edited me. He would read my reports and say "I don't understand." It was infuriating, because he was close to the smartest person I knew and how could he not get it? I would get emotional and explain, passionately, that the present was LIKE THIS and the future would be different, LIKE THAT, and decision-makers at companies needed to understand and act on that knowledge. NOW do you get it, Bill?
Then we'd both look at each other and realize that I'd gotten to the heart of the matter in a much more understandable way. I'd go back and write what I'd said to him, and the report would be a whole lot better.
When Bill died, I resolved to take on what I could of his editorial persona. By then, I had helped create Technographics and had developed somewhat of a reputation based on my analysis of the television world. This meant that many people inside and outside Forrester assumed I knew what I was talking about -- I was secure in that reputation.
This meant I could assume -- perhaps egotistically -- that if I didn't get something, the problem was with the content, not with me. And I determined to do what Bill did.
When I read a report, I often say "I don't understand, what's your main point?" At this point the writer often reacts as I did with Bill, and we get closer to a better explanation. Or she reveals that in fact, she doesn't know what she's talking about -- the problem is in idea, not in the writing -- and we send her back to clarify and strengthen her ideas.
It works in meetings, too. It clarifies people's thinking.
I do this with clients, too. When I look at someone and say "I don't understand," the result is a deeper explanation . . . or sometimes, revealing that they need to work harder on clarifying what their issue is.
As of this moment, I encourage you to do this. It takes confidence to say "I don't understand" since the easiest reaction on the part of the person you're talking with is to assume that you're stupid. And you will get ridiculed. But you might learn something, too. You might get a better explanation. You might help the person you're speaking with clarify his ideas. And you might just both end up in a better place.
As Isaac Asimov said, "The most exciting phrase to hear in science, the only one that heralds new discoveries, is not 'Eureka!,' but rather, 'Hmm ... that’s funny....'"