The better, more subtle interpretation is that failure is a manifestation of learning and exploration. If you aren’t experiencing failure, then you are making a far worse mistake: You are being driven by the desire to avoid it. And, for leaders especially, this strategy - trying to avoid failure by out-thinking it - dooms you to fail. As Andrew puts it, “Moving things forward allows the team you are leading to feel like, ‘Oh, I’m on a boat that is actually going towards land.’ As opposed to having a leader who says, ‘I’m still not sure. I’m going to look at the map a little bit more, and we’re just going to float here, and all of you stop rowing until I figure this out.’ And then weeks go by, and morale plummets, and failure becomes self-fulfilling. People begin to treat the captain with doubt and trepidation. Even if their doubts aren’t fully justified, you’ve become what they see you as because of your inability to move.

Bill’s perspective was that it’s a manager’s job to push the team to be more courageous. Courage is hard. People are naturally afraid of taking risks for fear of failure. It’s the manager’s job to push them past their reticence.

For example, meeting with senior executives in a large financial services firm in April

2020, I listened as they explained that the current business environment made failure temporarily “off-limits.” Understandably concerned about an economic climate increasingly challenged by a global pandemic, these business leaders wanted everything to go as well as possible. Generally speaking, they were sincere in their desire to learn from failure. But enthusiasm about failing was acceptable when times were good, they told me; now that the future looked uncertain, pursuing unerring success was more imperative than ever. These smart, well-intentioned people needed to rethink failure. First, they needed to appreciate the context. The need for fast learning from failure is most critical in times of uncertainty and upheaval, in part because failures are more likely! Second, while encouraging people to minimize basic and complex failures may help them focus, welcoming intelligent failures remains essential to progress in any industry. Third, they needed to recognize that the most likely outcome of their prohibition on failure wasn’t perfection but rather not hearing about the failures that do occur. When people don’t speak up about small failures—say, an accounting error—these can spiral into larger failures, such as massive banking losses.

The instinct to exhort people to do their best work in challenging times is understandable. It’s tempting to believe that if we just hunker down, we can avoid failure altogether. It’s also wrong. The relationship between effort and success is imperfect. The world around us changes constantly and keeps presenting us with new situations. The best-laid plans encounter problems in an uncertain context. Even when people work hard and are committed to doing the right thing, failure is always possible in a new situation. Sure, sometimes failures are caused by people who are careless or don’t work hard, but even hard work can end in failure when a situation is new and different or some unexpected event happens. Finally, and most perversely, sometimes sheer luck allows you to mail it in and succeed anyway.

Now consider what happens when senior executives, or parents, for that matter, state unequivocally that failure is off-limits, that only good results are acceptable. Failures don’t stop. They simply go underground. Unwittingly, the financial services executives I spoke with were at risk of inhibiting the transmission of bad news. That wasn’t their goal. Their goal was to encourage excellence. But it’s human nature to hide the truth when it’s clear that sharing it will bring punishment—or even just disapproval. Our fear of rejection presents the third barrier to practicing the science of failing well.