Great post from Cathy about the need to be able to assert uncertainty in a, well, assertive way. Why is this so hard? Why do we find people trustworthy when they say, with complete confidence, “Here’s your answer?”
One reason must be that in some contexts, confidence really does correlate with knowledge; people who truly know nothing about a subject are (hopefully) more willing to express uncertainty about it. So when we hear someone answer a question with “I’m not sure,” we have to carry out some inferential computation: do we think they’re saying that because they’ve never thought about the question, or because they’ve thought enough about the question to understand that it’s actually difficult?
I don’t have an answer to this conundrum, but I do have an extremely scientific infographic that I hope will illustrate the issue.

As Pope wrote:
“A little learning is a dangerous thing;
drink deep, or achieve Peak Bullshit rating on JSE’s graph.”
Here is a thoughtful article about this effect, which is pretty well studied.
http://arstechnica.com/science/2012/05/revisiting-why-incompetents-think-theyre-awesome/
I recall reading a book based on the See It Now broadcasts of the 1950s, with transcriptions of the presentations. The episode about Princeton’s Institute for Advanced Studies included Edward R Murrow commenting that he heard “I don’t know” from adults more during his time there than anytime in his life.
Related illustration: http://www.smbc-comics.com/?id=2475
I once went to a lecture on the financial crisis from a former big bank senior guy who was dabbling in academic things. He had a very assertive manner, and I’ve remembered his “I don’t know”: he said, “There is no known answer to that.”