Leaders: Embracing your fear of failure can make your team better. Here’s why

Failure comes with the territory sometimes. The trick is to avoid feeling demoralized by shame.

In business, the way we define and think of failure is crucial to enhancing our ability to learn from it. We must first recognize that failure can be a major determinant for success, no matter the discipline.

No one wants to fail publicly. It’s difficult to work hard only to risk others knowing you’ve failed, which for some people may create feelings of humiliation or upset that can fester into self-doubt. Psychologists posit that a fear of failure is really a fear of shame, a more toxic emotion that eats at the core of our egos and our self-esteem. Some solutions to this fear, he says, are confronting and accepting those emotions and reframing challenges to focus areas within your control.

Both of those are easier within a support system that practices avoiding shame by talking about failure in a healthy way. Building a culture where failure is acknowledged, if not celebrated, is crucial for progress and advancement. What you do with those challenging moments is what makes the difference. How can you redirect your thinking around failure to erase shame and learn from missteps?


Ensure that your team knows it’s okay to fail. When a single Amazon Web Services (AWS) engineer pushed a production change that caused a failure of the entire East AWS region (and therefore, a huge portion of the internet), AWS explained that of course the developer wouldn’t be terminated. While he had made a mistake, the the failure lay in a system that allowed for the mistake to be made, and the virtue would come from learning and improving from it.

To cultivate a similarly healthy relationship with failure, get into the habit of having your team perform root-cause analyses when things go wrong. The Five Whys technique, pioneered by Toyota in the 1930s, can serve as a great framework for ensuring you’re digging to the true cause of every failure.

At the end of a root-cause analysis, we have our team present their findings company-wide. Like the time we pushed 960,000 test notifications out to a quarter-million people on production. Similar to the AWS failure, this big failure manifested as a string of smaller related failures that cascaded to cause the event, a problem that possibly could’ve been prevented with a more consistent confrontation of failure.

No failure should be a tar-and-feather shaming event; it’s an opportunities for the rest of the organization to learn from mistakes, identify what questions to ask if they’re working on similar projects, and remain vigilant (especially with production environments).


We’re conditioned to focus on “big” failures: a failed product launch, lost sale, or any other unmistakable instances of falling short. When a miss doesn’t rise to that level of failure, we’re often biased to consider it “close enough” or at least a draw. It’s too easy to dismiss the small failures or missteps. If they don’t carry a significant cost, or if they’re fairly easily resolved, then we can brush them off as typical. But I’ve found if I take a few moments even to examine the little ways something didn’t go as planned, I can learn a lot.

Dismissing small failures leaves on the table a lot of opportunities for self-improvement and learned experiences that can result in future good judgment. It takes some doing, but conditioning yourself to view even small misses or failures as opportunities to learn and pivot forward is one of the most important skills you can learn running a business.

It may sound like an obsessive level of living in the past, but once you start incorporating some level of failure analysis into almost everything, it turns out you can identify pretty quickly where things went wrong. Do that enough, and you start to see potential failures on the horizon before it’s too late.

Try to take the time to evaluate what went wrong, even for small problems. Once you start playing back events in your mind, you’ll find that doing that exercise gets you thinking differently and empowers you to consider problems from different angles.


Recognizing and learning from failures means taking the focus off yourself. Leaders must demonstrate the no-ego mindset and build a culture that encourages the same by openly acknowledging failures and staying open to feedback.

When the culture is one where employees can admit to mistakes, leaders can help them grow faster by knowing which problems to address. On the other hand, if employees keep their mistakes or shortcomings to themselves, they can experience imposter syndrome. It’s a dangerous spiral: Employees begin to flounder alone, too embarrassed to ask for help, and they grow increasingly worried about their performance. The entire process only escalates over time.

But when people feel like they have agency to fail openly, they’re likely to learn from those failures together. More importantly, they’re likely to ask for help early and often, and perhaps avoid those missteps altogether.

Failure can be demoralizing, frustrating, and exhausting. Understandably, trying to use it to excite and empower further attempts is far easier said than done. But when taken in the context of these other strategies, it can be a motivating opportunity to get back on the horse and try again with the experience you’ve just gained.

Chris Cardinal
Chris Cardinal
Chris Cardinal is a founding principal of Synapse Studios. His primary focus is on business development but enjoys helping architect software solutions for clients.

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