The problem with mistakes is that managers don’t learn from them. Alina Tugend, in the November 24 issue of The New York Times, writes cogently about the way we think about mistakes. She identifies the dichotomy we hold in our heads: 1) we learn from our mistakes, i.e., mistakes are a good thing; and 2) only success should be rewarded, i.e., mistakes are a bad thing. From a very young age and throughout our work-lives we hear this mixed message. Although managers know, intellectually, that “everyone makes mistakes” and mistakes are just part of risk-taking and being creative, managers fear failure and being exposed as less than perfect. Schoemaker and Gunther, in a June 2006 article in Harvard Business Review titled The Wisdom of Deliberate Mistakes, say that managers end up spending “a great deal of time and energy trying not to make mistakes.” They argue that, instead, managers should take some actions that are likely to fail in order to provide themselves with the opportunity for learning.

Real entrepreneurs do not have a fear of mistakes. In a story in the December 2007 issue of Inc. Magazine titled, Everybody Wants to Save the World But When You Start a Charity Overseas, Good Intentions Often Go Awry, the author tells the story of serial entrepreneur Troy Wiseman who started a philanthropy in 1992 to establish orphanages around the world and discovered after twelve years and investing hundreds of thousands of dollars of his own money that many of the orphanages didn’t exist or weren’t using his money wisely and he was seeing no impact. At that point he changed everything to achieve greater accountability and success. Wiseman said, “Entrepreneurs aren’t scared of making mistakes. We make our mistakes. And we learn from them.”

Organizations that want new solutions to old problems, that want creativity and innovation in their operations and products, that want employees to “think outside the box” and to “walk the talk”, need to allow managers to make mistakes and learn from those experiences. I would argue that this learning cannot be left to chance. At a minimum, all mistakes (errors, failures, screw-ups, etc.) should be followed by a non-punitive conversation between manager and boss about what happened, what was learned, and what should be done now to be successful in the future.