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.

There’s a quick way to determine if your company has embraced the negative definition of failure. Ask yourself what happens when an error is discovered. Do people shut down and turn inward, instead of coming together to untangle the causes of problems that might be avoided going forward? Is the question being asked: Whose fault was this? If so, your culture is one that vilifies failure. Failure is difficult enough without it being compounded by the search for a scapegoat.

In a fear-based, failure-averse culture, people will consciously or unconsciously avoid risk. They will seek instead to repeat something safe that’s been good enough in the past. Their work will be derivative, not innovative. But if you can foster a positive understanding of failure, the opposite will happen.

So if your primary goal is to have a fully worked out, set-in-stone plan, you are only upping your chances of being unoriginal. Moreover, you cannot plan your way out of problems. While planning is very important, and we do a lot of it, there is only so much you can control in a creative environment. In general, I have found that people who pour their energy into thinking about an approach and insisting that it is too early to act are wrong just as often as people who dive in and work quickly.

When considering whether to lead with context or control, the second key question to ask is whether your goal is error prevention or innovation… But if, like Target, your goal is innovation, making a mistake is not the primary risk. The big risk is becoming irrelevant because your employees aren’t coming up with great ideas to reinvent the business. Although many brick-and-mortar retailers have gone out of business as increasing numbers of people shop online, Target has made a priority of imagining fresh ways to get customers into the stores.

It stands to reason that social media is shaping our behavior in ways that make sharing problems, mistakes, and failures harder than ever. Both research and firsthand accounts focus on the harmful effects of constant exposure to others’ success, fun, and photoshopped perfect looks. Explicit mentions of failure, or failure avoidance, are rare, and social media’s emphasis on unblemished successes further inhibits healthy attitudes toward failure. Spending considerable time on social media creates a risk of seeing ourselves as failures by comparison to the edited lives that others are living.