The first good lesson to take from Dale Carnegie's How To Win Friends and Influence People is: Don't treat people likey they're stupid (or cheaters, crooks, punks, or otherwise undesirable).
Carnegie points out the story of a murder who described himself thus: "Under my coat is a weary heart, but a kind one--one that would do nobody any harm." His point was that no one, not even a brutal murderer sees himself objectively and certainly doesn't want to be confronted by his weaknesses.
While I'm not a bona fide web designer, I think that in this modern era, one needs to consider the way that a web site might make someone feel as she uses it. If the user can't navigate the web site easily, she will feel frustrated and even a little stupid. How likely would you be to return to a web site that makes you feel stupid?
Not treating people like they're stupid is also important for managers and executives in any company. Given that employees don't want to feel stupid, do you think they want to have you point out their flaws at every turn.
One basic technique that allows you to avoid plainly pointing out faults to your people is to ask a genuine question about the issue. I can think of times when I've indignantly pointed out an obvious mistake to one of my team members only to have her explain why I was the one who didn't understand. So I look like an idiot and she certainly doesn't feel any better being backed into a corner and forced to make me look stupid. I'm learning instead to ask a genuine question, like "Can you help me understand your analysis by walking me through it?"
By working through the analysis together, we discover weaknesses together and both our dignity is preserved.
Applying this thinking to the relationship between venture capitalists and entrepreneurs can also go a long way toward building successful relationships there, too.
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