One of my favorite work maxims is: If you’re not fucking up, you’re not trying hard enough.
I try to drive this home with all of my teams in all of my projects. But what does it actually mean, and how do you actually create a culture that encourages this?
Baseball offers some beautiful insights into this. In baseball, if you manage to hit the ball successfully 30 percent of the time over the course of your career, you are considered a great hitter, quite possibly a Hall of Famer. That means you’re “failing” 70 percent of the time. But no one thinks of it that way, because hitting a tiny baseball coming at you at 90 miles per hour from 60 feet away is freakin’ hard.
If you’re going to adopt this attitude in your own work, you have to be clear about what a good success rate actually is, and you have to celebrate when you achieve that rate. In Silicon Valley, for example, most VCs are in the high-risk, high-reward business. Many VCs cite a 10 percent hit rate as success. If they hit that rate, they celebrate.
With some of my projects, I go so far as to add, “Failure of effort” to my checklist of success. For example, in my second Changemaker Bootcamp pilot, I had one workout that went horribly awry. I actually checked that off as a success indicator, because it gave me confidence that I was really testing the model rather than playing it safe.
The other important thing to do is to differentiate between different kinds of failure. I like to think of it as failure of neglect versus failure of effort. One of my favorite coaches in baseball always says that he’ll never complain about a player getting thrown out trying to steal, because it’s a failure that stems from effort, not neglect. (Stat geeks object vociferously to this strategy, but that’s a topic for another day.)
With my teams, I try to go out of my way to reward people for failure of effort, because I want to encourage people to follow their instincts and take risks. I’m not always good at this, especially in high-stakes situation.
Last July, we had a terrible Delta Dialogues meeting, which was documented in our final report. There was one moment in particular when one of the facilitators advocated strongly for a particular move that the rest of us did not feel good about. I supported it anyway, because I understood his reasoning and because he felt so strongly about it. The move didn’t work, and he felt awful about it.
In our debrief, I tried to state as clearly as possible that, if I had to do it again, I would do exactly the same thing. We were dealing with a lot of complexity, and we had to make strong moves if we were going to be successful. That meant we were going to make mistakes, and we needed to be okay with mistakes of effort. I wanted my teammate to understand that I supported him and believed in him, and a mistake of effort wasn’t going to change that.
Still, I’m not sure I conveyed that message successfully, because I was absolutely dejected by the overall outcome, and I was probably sending very mixed messages. In particular, I didn’t think we had prepared adequately for the meeting — failures of neglect — and I was very angry about that.
In the end, it all worked out. We were ultimately honest with ourselves about what we controlled and what we didn’t, and we made a lot of adjustments based on what had happened. In a followup meeting two months later, my colleague made the exact same move. This time, it was perfect, and that meeting ended up being the best one of the whole project.
The key to doing anything hard is to strive for perfection, but to expect a certain amount of failure. In practice, this is hard, especially when you’re a high achiever used to a certain level of success. Your ability to embed this mindset into structures (such as your success checklist) will help you do this more effectively, but at the end of the day, it’s all about practice.
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