All great points. I'm a huge fan of Kahneman's work, and I think that the related concept of loss aversion is a big hindrance to risk-taking and innovation (we hate losses--of time, of money, etc.--more than we love gains). It would be interesting to think of loss aversion and opportunity cost together: how can we frame the failure to take risks and innovate as a loss/cost for the school or organization?
What I love about the pre-mortem idea is its embrace of pessimism, which is often, I think, seen as an undesirable--and not particularly useful--quality in a team member. Pessimism about a project's success might be the best way of identifying flaws, risks, assumptions, etc. Optimism is key for any individual or team, but unchecked optimism can end up blinding us.