What does experience buy an employee? It buys a body of knowledge to draw upon. Reflecting upon the nebulous “things that went wrong,” savvy veterans can provide great value to a company by using the lessons learned from past failures to steer clear of disaster on future projects.
But this is only in the perfect case.
In the real world, most people do not have the capacity to remember specific examples of what they’ve seen. Instead, most leaders that I have worked under develop a “gut feeling” that guides their judgement. If asked to substantiate the gut feeling, these leaders can be evasive, because without being able to remember the examples, one might not be sure what specifically led to that feeling being formed. Instead of the example that brought about the feeling, they will more often cite a recent-but-not-too-relevant example that comes to mind.
As a leader, I have found that I am as guilty of this as the leaders before me. I do not have the ability to remember every situation that has led to my gut feelings, and so I can sometimes find myself unable to substantiate even my “stronger” gut feelings.
Now, the fact that we tend to develop a gut feeling that we can not explain is not in itself a problem. If your gut feelings are correct within the context that you assert them, fine.
But here’s a little secret that I think is the key failing of many highly experienced leaders: their gut feeling is to avoid risk, and while that gut feeling is understandable, it is also stupid.
Think about it: indiscriminately avoiding risk is the natural culmination of years of collecting examples of things that go wrong. First you work on a project that was overly ambitious and got overscheduled, so you remember to keep your scope refined. Then you work on a project that used very elaborate systems that caused you to run out of memory, so you remember to avoid very elaborate systems. On a third project, you try a new 3d algorithm that ends up being thrown out during alpha because of low-level incompatibilities, so you remember to be wary of new algorithms.
Combine all of those lessons into one lesson and what do you get? At the most abstract level, all three of these examples suggest that by taking a risk (large scope, elaborate systems, new algorithm) the project suffered.
This is why I believe that many experienced people learn to avoid risks as a habit. And this is why I make it a point not to learn from my mistakes.
You can not make significant innovations without taking significant risks. Yes, you expose yourself to second-guessing, particularly if your risks have failed before. And yes, it is far more difficult to implement a nuanced risk-aversion plan that considers the specific reasons behind past failures, rather than simply avoid all possible risks that could beget failure.
But as an employer, I believe that the holy grail of maximal ass-kicking job applicants are those that have been through projects before, failed, but are just as willing to push the envelope as they had been during their first project. They need to have learned something from their failures so as not to be derelict, but learning to simply avoid risk is the recipe for perpetual sterility.