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Is Failure Good?


The other day, I was listening to a great version of Leonard Cohen’s song Anthem. The most famous line of the song is “there is a crack in everything; that’s how the light gets in.” In that line Cohen is reminding us of two important concepts.


One, nothing is perfect. Everything has a crack in it.


The second is that growth occurs because of these imperfections. If something is perceived as being perfect, it will never change; it will ossify. Without change, growth and improvement cannot happen. The light that gets in through the imperfection should guide us to wise change.


Oddly, if you read leadership literature, it seems that many authors think failure is a laudable goal. Great leaders, we are told, “fail fast.” These same leaders are implored to “fail forward.” Clearly, this literature is trying to tap the same well as Cohen. Progress comes after analyzing mistakes and creating a new and better plan.


When I was leading schools, every now and again, we would have to “counsel a student out.” (A euphemism for removing a student from school.) Early in my career as a Head, when we counseled a student out, I would tell the team that we (I always included myself) had failed. We had failed the student, and we had failed their family. In some ways we also had failed the community as they know that our love for all community members was not unconditional. I would mention we should see this as an opportunity to fail forward. Unsurprisingly, I got more pushback than people willing to strategize about how to do better. Why?


When Duke School started studying Design Thinking, it became clear that making mistakes as you endeavored to solve a problem was an integral part of the process. However, these missteps were not labeled failures (forward or otherwise) but rather iterations. The design process is one of iteration.


Words have power. “Fail” has negative connotations (despite the leadership literature) and telling people they failed tends to demotivate them. “Iteration”, on the other hand, has a positive connotation. People who are iterating are looking at other potentials and positively moving forward. Almost everyone prefers to iterate rather than to fail.


It is true that the light gets in through the cracks. It is true that the light can illuminate better approaches. It is also true that the group believing it is iterating is more likely to see better approaches than the group who is trying to leave failure behind.


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