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Failure: Building a Team Culture Where It’s OK to Lose

Does the possibility of failure make you nervous? Learn why you should fail fast, fail often, and fail spectacularly.

By Samantha Rae Ayoub  •   March 17, 2022  •   6 min read

I recently started a new position on the executive team at a Canadian non-profit specializing in health research. Like with any new job, I had a healthy dose of nervousness my first week – What would the team be like? What challenges would come my way? How long would it take me to get up to speed? Was I even going to be good at this?   

One of my first tasks was to work with my new team to support the release of a new research paper that was sure to get some attention from national media. Everything was going great – plans were developed, content was approved, our partners were engaged – we were ticking along and having fun too! I had checked and rechecked all the metaphorical boxes and we were ready… or so I thought. As it turns out, mere hours after the paper was released I realized we had accidentally forgotten to mention the name of one of the researchers in our public content – facepalm!  

What’s interesting though is what happened next – my team sprung into action suggesting strategies to redevelop and republish the content, one of my colleagues from another department actually chuckled and said “Oh geez, we missed that didn’t we?” And when I informed my boss, her reaction was similar, “Oh crap, we messed that up didn’t we? What’s in the works to get it fixed?” 

I was pleasantly taken aback. No one was upset, there was no finger-pointing, no lecturing, no scapegoating – nothing. And what’s more is that everyone was using the word “we!” I didn’t personally fail, my team didn’t fail, rather the failure was communally shared and owned. I sat with that feeling for the rest of the day thinking “wow, this team really knows how to embrace failure!” – and I was proud to be part of it! 

Why are we afraid to fail?

The concept of embracing failure isn’t new – especially for those working in science, technology, Silicon Valley, and start ups. People fail fast, fail hard, and start again. In fact, in some industries and workplaces failure is simply viewed as a stepping stone to success. You have to fail first to succeed later – makes sense, right? 

Why then are so many workplaces across the country afraid of failure? Why are people in general afraid to fail? Why is your direct reporthttps://staging.fellow.co/blog/management/running-your-first-one-on-one-with-a-new-direct-report/ nervous to tell you when they make a mistake? While I’m sure there are many reasons (and I’m also not a psychologist!) here is my hunch: failure is often more public than success – and that my friends is terrifying! 

Think about all the failures you see in one day: you read the paper in the morning and the government of the day is failing at something, so-and-so celebrity lost an advertising deal due to a mistake they made, you didn’t close your rings today on your Apple Watch and now all your friends know, you burned dinner and now your child is upset, the couple you’re rooting for on Amazing Race didn’t make it to the podium in time, the dog is glaring at you because you’re fresh out of treats – sigh. Failures both big and small are around us every day and we, as a society, have a hard time sifting through all of that noise. Failure is in our face so often that we’re afraid of it – we don’t want to fail, we want to succeed.

Focus on the good

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Now think about the successes you see day-to-day. Struggling a wee bit, are we? One of the reasons you may have a hard time reflecting on success is due to negativity bias. Negativity bias is a well-studied concept that explains that our emotional response to negative events is often amplified compared to similar positive events. In short – we like to focus on all the bad over all the good. 

In a round-about way, this proves my point: When you succeed, your brain often skips by it quickly. You reached your goal – cool, good for you, onto the next goal. When you fail on the other hand, you feel terrible about it, you lament, people around you notice, you lament some more, and it feels, well – icky. As I said, failure is always more public than success – and we’ve been conditioned to believe that failure sucks.

Building a team culture where it’s OK to fail

When I think about failure in the business world, I think about John Maxwell’s book, Failing Forward, which explains that if we want to succeed, we really have to fail first. In that book Maxwell says: 

“In life, the question is not if you will have problems, but how you are going to deal with your problems. If the possibility of failure were erased, what would you attempt to achieve?”

Let that sink in for a sec. Is there something that you are simply not attempting because you’re afraid to fail? Is your team holding back in some way because they’re afraid to make a mistake? 

Now think about Robert F. Kennedy’s famous quote, which inspired some of the work of Brené Brown in Daring Greatly

“Only those who dare to fail greatly can ever achieve greatly.” – Robert F. Kennedy

Countless authors and researchers have studied failure and concluded that failure is not only an important part of success, but often a vital ingredient to success. Rationally, we all know this – it makes sense. So how then do we overcome our fear of failure, embrace it, and even “teach it” to our teams and direct reports? Here are a few tips:

1 Redefine failure and reject rejection

This is perhaps the lesson that stuck with me the most after reading John Maxwell’s work on failing forward. Redefining failure really is about shifting your mindset to appreciate that failure is not actually failure, rather it’s an opportunity to learn, a way to refine, a way course-correct. In this same vein, the notion of rejecting rejection reminds us to maintain a positive and healthy self-image. Don’t let other people’s perceptions of you influence your thinking or get you down. Make it your team mantra – redefine failure and reject rejection!   

2 Share wins and losses regularly 

If you’re looking for a baby step in getting your team to embrace failure, this is it! In your meetings or perhaps in your one-on-ones, get in the habit of asking team members to share wins and losses, also referred to as highs and lows. Over time, team members will gradually become more comfortable sharing their blunders.  

3 Be ok with being uncomfortable 

Riffing off of Robert F. Kennedy, in order to achieve great success, you must also not be afraid to fail in spectacular fashion. Encourage your team to try new things and share what worked and what didn’t. Push your team members out of their comfort zones and then get out of the way. Only two things can happen – spectacular success or spectacular failure, and both should be celebrated. 

4 Make sure you learn the lesson 

We’ve established that failure is an important component of success, but that doesn’t mean that failing in the same way over and over again is a good idea. When your team fails, sit in the muck, feel the feelings, and make sure everyone has learned the lesson – applaud and celebrate the lesson even. And then, when everyone is ready, try again. 

Remember that failure is not the opposite of success

At the end of the day remember: Failure and success may go hand in hand, but they are not necessarily opposites – rather they complement one another. 

 “We need to accept that we won’t always make the right decisions, that we’ll screw up royally sometimes – understanding that failure is not the opposite of success, it’s part of success.” ― Arianna HuffingtonDon’t be afraid to embrace failure personally and on the teams you lead. Learn from failure, pick yourself up, and – above all else – always try again.  

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