I read, enjoy and learn from Jeffrey Phillips' blog, Thinking Faster. Most often, I agree with what he has to say. Monday, though, he said,
"I understand the rationale for seeking out the likely problems and trying to mitigate them early, but often I think we create a negative mindset by constantly planning not to fail."
While I agree that we don't want to kill optimism, looking for problems in our plans is a key to success. Failing to look for potential problems is planning to lose, in my book.
In my experience, we most often don't look hard enough at what could go wrong with a plan. It may seem pessimistic, but I have seen real results from double-checking an excellent plan and finding potential problems.
I have written about Potential Problem Analysis before, and told a story of a real life application in New Zealand. In that operation, Potential Problem Analysis had a major positive impact on profits. Because of that success, Potential Problem Analysis became a way of increasing confidence that our plans would have excellent results. Rather than create pessimism, looking for potential problems created data-based optimism.
I recently reviewed a book by Raymond Nickerson, called "Cognition and Chance" which was about how we perceive probability. One of the findings was that we habitually underestimate time and cost - we assume every step of a project will go perfectly well, when chance favors the opposite assumption.
Bottom line: our plans are most often over-optimistic. It isn't pessimistic to look for potential problems. It is realistic.