How to Fail: Your Simple Guide to the Benefits of Failure

Your simple guide to the benefits of failure

The subject of failure holds a special place in my heart, and I am qualified to speak about it because I have failed a lot. Some of it directly resulted from my actions, and sometimes I wasn’t set up for success.

Still, I have failed so many times and in so many unique and inspiring ways that when I am interviewed about my life, the questions indubitably make their way around to one subject: Resilience.

“ZJ, the events of your life have been such a never-ending horror that we hesitate even to put it in print; what can you tell our readers about resilience?” they say.

(Okay, they don’t say it, but I can read between the lines.)

I used to ponder the word. Resilient. What did it mean? Did it apply to me? I’ve never felt remarkably resilient.

After a grand failure, I typically take to the living room floor, staring straight up at the ceiling with tear-filled eyes, interrupting my deep ennui only long enough to snap a moody selfie or two. Reminiscing about days unremembered when a dejected woman could simply take to the attic in a long black dress and spend the rest of her life discreetly tended to by a wealthy cousin.

Sad person who has failed — I’ll be in the attic. (Photo by benjamin lehman)

Eventually, I would get hungry and get up to make a snack. I would listen to ANGRY YELLING MUSIC and stomp until my neighbours pounded on their ceiling. The next day, the sun would rise, and, my ennui abandoned, I would get up and try again.

Little did I know, dear reader, that getting up and trying again, however reluctantly, is resilience. It’s resilience even if you hate it, are embarrassed, and even — maybe especially — if you cry.

The thing that’s hard to see while you’re lying on the floor is this:

Both success and failure build confidence.

It’s easy to see how success builds confidence. You weren’t sure you could do a thing, but you tried it, and it went well. Congrats — you can do the thing.

When you fail, it can be harder to see the benefits of your failure because all kinds of messy feelings get in the way.

Embarrassment, shame, disappointment, sadness, despair, frustration, and so on. Feelings that are valid. Feelings that, reasonably, we would all prefer to avoid.

Failure to put ice cream on cone — Failed to put ice cream on cone. (Photo by Josephina Kolpachnikof)

In the moment, failure is bad.

But in the future, past failures can be very, very good.

The next time a similar situation rolls around, when enough time has passed, you can look at it differently. If there were previously two options, now only one is clear — you already know the other option leads to failure. You have learned from your failure.

And the learning is the thing.

. . .

As IBM’s Thomas Watson Sr. once said, “The fastest way to succeed is to double your failure rate.”

So, what if we could reframe failure as part of the path toward success rather than a dirty little secret?

Let your employees fail!

In professional settings, especially, failure is often deemed inexcusable. This generates an environment of fear that dampens creativity and independent thinking.

Nothing good comes from a climate of fear.

Take Volkswagen, for example.

Former CEO Martin Winterkorn held high expectations for his employees, paired with a zero-tolerance policy for mistakes. He created a work climate rooted in fear which actively worked against the lofty goals he set for the company.

The result was the 2015 emissions scandal, when the EPA reported that Volkswagen had violated the Clean Air Act with software developed to fool emissions testing.

Volkswagen is a company with thousands of brilliant employees who could have crafted an emissions-efficient diesel engine, but instead focused their energy on covering the failure of their initial attempts. The scandal was born from the fear of failure that was fostered by Winterkorn.

Don’t be a Winterkorn.

With failure comes success

Failure tolerant environment — Burny fire bad, soothing water good.

Instead, create a failure-tolerant workplace to encourage transparency and accountability.

The goal is to create an environment where learning is encouraged and mistakes are viewed as part of business.

This prevents hiding issues that then become a Volkswagen-sized fiasco.

How?

First, recognize that your employees will screw up at some point. That’s inevitable. To generate a progress-focused work environment, leadership must understand that failure isn’t the opposite of success. It’s simply part of the learning and development process.

Reframe the concept of failure. Failure isn’t an end-point, but rather a stepping stone. Communicate with your team how mistakes are part of the learning process.
Lead by example. Share lessons that you’ve learned through trial and error. Encourage team members to do the same to normalize imperfection. If your team currently documents their wins, consider adding a “lessons learned” tally to the record. It will allow you to visualize growth from a fresh perspective.
Maintain a wide perspective. Especially for team environments, remove focus on individual failures and successes, instead focusing on holistic progress. It isn’t personal! This creates an additional layer of psychological safety, encouraging team members to be forthcoming with their lessons learned.

What is team psychological safety? It’s the shared belief held by team members that it’s OK to take risks, to express their ideas and concerns, to speak up with questions, and to admit mistakes — all without fear of negative consequences. — Harvard Business Review

Open communication channels. Encourage open communication, honesty and transparency amongst your team. When failure is encountered, use it as an opportunity for feedback and workshopping solutions.
Focus on learning. Growth occurs through learning. Learning happens in the sweet spot known as the “stretch zone.” After becoming aware of a mistake, your employee will exit their comfort zone, which is a prime learning opportunity.
Explore the “why.” When blunders occur, explore why they happened. Uncovering the circumstances surrounding a failure allows you and your team to identify what can be learned from the experience. Plus, it offers an opportunity to build better processes that incorporate trial and error.
Note, I’m not recommending pulling out the interrogation lamp. It’s important to ask questions with the intent of understanding how and why the failure occurred. It’s an open conversation, not a one-way barrage of questions.

Resist the urge to helicopter

As a leader, it can be tempting to step in and solve problems for your team members.

It’s a natural urge to take control and just fix it, what I imagine parents feel when they see their child putting their clothes on inside out.

But, just as with helicopter parenting, being a helicopter manager hinders your team’s success.

Trying to control outcomes effectively undoes an environment of psychological safety.

Failure helicopter — A slide from a workshop I did on failure recently. That’s right, you can pay me to say these things out loud too!

Negative impacts of helicopter management on employees:

Loss of self-confidence
Increase in stress
Poor problem-solving skills
Lost learning opportunities

The last point, lost learning opportunities, is the real kicker.

When you handle problem-solving for your team members, they miss out on the critical learning-zone opportunity of making a mistake.

Fostering a learning culture

Managers fostering a learning culture approach everything with curiosity, with a focus on collaboration.

Rather than offer solutions, a failure-tolerant manager offers support and guidance with the goal of the employee identifying a pertinent solution themselves.

This is admittedly easier said than done.

It’s challenging to let people fail, especially when you see that someone is about to make a mistake. Your instinct may be to intercept and correct the issue before it materializes. But, really, don’t.

Think about the biggest lessons you’ve learned throughout your career. Were they as a result of a manager telling you how to do something differently, or were they because you f*cked up and learned from it?

For me, clearly, it’s the latter. When we fail, it forces us to evaluate the situation, what went wrong, and how to prevent it from happening again.

The role of a good manager is to help guide their reports to that lesson. This is why an environment of trust and honest communication is critical. If your employees are scared to come to you with their issues, you can’t help ensure that failure leads to future success.

The next time an employee comes to you with a problem, don’t concern yourself with identifying a quick fix.

Instead, direct the conversation with questions such as:

What problem are you having?
How does this fit into or impact your goals?
How are things going with your project?
Have you considered the long-term effects?
What next steps are you considering?

The conversation should be “less about whether the project is succeeding or failing than about what can be learned from the experience.” — Harvard Business Review

After all, both success and failure have benefits.

The only way to lose is to not try at all.

. . .

I’m Begging You to Start Holding Retrospectives

When I worked in live theatre, following a rehearsal, we would all gather at the edge of the stage for what we called a “post-mortem.” Without assigning blame, we would dissect what went well and what didn’t from that night’s run-through. Cues would get tightened, quick changes would get lengthened, actors would complain that the practical food was, again, an undesirable temperature.

Post mortem translates literally to “after death” — and it refers to an autopsy. Many companies prefer the term “retrospective” or, simply, “retro,” for reasons I guess must be obvious to them.

A retrospective takes place after a project has been completed. The goal is to look at the project from beginning to end and identify what went well and what could be improved.

By looking at the entire project (or sprint, or rehearsal) the focus should be on how everything came together rather than each person’s individual successes or failures.

How to Run a Retro

Gather and prioritize talking points. I like a tool called EasyRetro, where people can submit and upvote talking points so that the most important subjects are what get covered.
Appoint a neutral moderator. Someone with less intimate knowledge of the project will likely ask better and more probing questions because of their natural curiosity.
Discuss the original goal or scope of the project, what went well, and what could be improved for next time.
Avoid using accusatory language or casting blame. Starting sentences with “you” puts people on the defensive — steer clear.
Summarize and end on a positive. The act of celebrating our successes reduces stress and increases optimism.
Implement changes.
Hold retros regularly, not just when things have gone terribly.