Failure is discussed a lot in leadership circles, mostly as something to be reframed into triumph. Fail fast. Fail forward. Every failure is a lesson. These phrases are not wrong exactly, but they tend to skip the part where you actually learn the lesson — which is harder and less photogenic than the reframe.
The thing I’ve noticed about genuine learning from failure is that it requires a particular kind of honesty most of us find uncomfortable. Not the public honesty of saying “I failed at this” — that’s become almost fashionable. The harder honesty is private and specific: Here is exactly what I did wrong. Here is the decision point where I chose poorly. Here is the assumption I was carrying that I should have examined.
This kind of accounting is unpleasant. It doesn’t feel like a lesson; it feels like a verdict. Which is why most of us rush past it, collecting the general principle (I need to communicate better, I need to plan more carefully) and moving on without sitting long enough with the specific thing to actually understand it.
I’ve learned more from two or three failures than from most of my successes. But the learning didn’t happen automatically. It required, in each case, a willingness to stay with the discomfort long enough to understand what actually went wrong — as opposed to the more comfortable story I would have preferred to tell.
The more comfortable story is always available. It features factors outside your control, other people’s failures, bad luck, timing. These factors are often real. They are also rarely the whole story.
A question I’ve found useful when processing a significant failure: What did I know at the time that I didn’t act on?
There is almost always something. A concern I dismissed. A sign I explained away. A voice in my own head that I talked myself out of. Getting specific about what I knew but chose not to act on is more useful than any general principle I could extract from the outcome.
It also makes me less likely to make the same choice twice.