13 Things Every Leader Should Know About Failure

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Failure has been a hot topic for several years, as innovators try to heed the words of Thomas J. Watson: “If you want to increase your success rate, double your failure rate” and Sir Ken Robinson: “If you’re not prepared to be wrong, you’ll never come up with anything original.”

But in the real world, failure sucks, and probably always will.

Humans have two natural and evolutionarily valuable tendencies that make failure feel especially bad.

  • Our negativity bias causes us to notice negative things in our environment, and judge them more importantly.
  • And loss aversion makes missing out on something feel much worse than winning the same thing. In other words, if I lose $100 this morning and win $100 this afternoon, I’ll still feel bad about the morning’s loss.

Not every idea is going to be a good one, but it’s essential nonetheless that we don’t shy away from having new ideas. So we need to become more comfortable with failure, be it independently or on a team.

I polled both literature on failure and my community of builders, thinkers, and troublemakers to find the best tips on how to create a more failure-tolerant team. Here are the best I found:

1. Make Small Bets

“I tell teams to ask themselves, “What’s the most important thing we need to learn next/first?” And then ask them, “What’s the least amount of work we need to do to learn that?” This way, if it’s wrong, we can more easily move on.”

Jeff Gothelf, Author of Lean UX and Sense and Respond

2. Celebrate

“I get teams to celebrate squashing bad ideas early. We look at how much time and money they saved by not pursuing it fully.”

Melissa Perri, Founder of Produx Labs

3. Extract Learnings

“Failures are not good in themselves. So, debrief each one and extract learnings that can be implemented.”

Mathias Jakobsen, LD at SYPartners and Lecturer at Parsons

4. Show Your Work

“People show work in an incomplete state to the whole animation crew, and although the director makes decisions, everyone is encouraged to comment.”

Ed Catmull, President of Pixar Animation Studios and Walt Disney Animation Studios

5. Let Yourself Heal

“Your brain can recover from strokes, infections, and all kinds of inflammation. It’s also wired to recover from failure. When you think yourself like a fallen and bruised child, you’ll find the capacity to accept failure and nurture yourself back to health so you can run again.”

Srini Pillay, M.D., CEO NeuroBusiness Group, Assistant Professor Harvard Medical School

6. Fail Fast

“There are different types of failure, not all worthy of respect; Epic failures, that only emerge after making large investments of time, treasure and emotion, are the arch nemesis; fast failures, that emerge when teams are free of existential angst, are incentivized towards outcomes and use enthusiastic skepticism to quickly uncover weak points in a plan, are the drivers of powerful discovery.”

Jonathan Bertfield, Senior Faculty at Lean Startup Co.

7. Eat Failure Cake

“It’s not the failure that we celebrate; it’s the learning, discussion and resulting action that follows. You should have a conscious process to learn from failures and fully own them, and we do that while eating our own failure cake.”

Barry O’Reilly , Founder and CEO of ExecCamp and Co-Author of Lean Enterprise

8. Celebrate More

“Focus on developing a culture that celebrates failure in a regular manner. Successes are always rewarded, but the culture of fear that comes with failure means that employees rarely admit failures, and sometimes that has additional costs and starts building a toxic culture.”

Anjali Ramachandran, Co-founder of Ada’s List , Former Head of Innovation at PHD UK

9. Pareto It

“In improvisation theater, there’s a principle that says you should succeed 80% and fail 20% of the time. If you succeed more often than that, you’re too much within your comfort zone. You’re doing things that are too easy for you.”

Sami Honkonen, Entrepreneur, Podcast host, Speaker, Blogger, Metal vocalist

10. Create Psychological Safety

“In a team with high psychological safety, teammates feel safe to take risks around their team members.”

Google Re:Work Team

11. Redefine Failure

“The only time an experiment fails is when it’s inconclusive.”

JB Brown, Director at Peloton, Former Head of Innovation at Nordstrom

12. Change Your Team Names

“Don’t name your teams after products. If your product ‘fails,’ then the team is often fired, which is pretty terrible in practice and culture.”

David J Bland, Founder CEO of Precoil

13. Consciously Consume It

“Get higher-level leadership looped in early to agree how they’d want to ‘consume’ failure. Specifically, on how it could be measured and reported. In other words, put reportable value on learning.”

Boris Grinkot, Innovation Strategy Consultant

One final caution I heard from almost everyone is that, while we can resist failure too much, we can also go too far in the opposite direction. Failure is not a goal, it is a tool–just like success. Help your teams and yourself become more accustomed to failure, but that doesn’t mean you need to seek it out. If you’re taking risks, it will find you anyway.