Failures, missteps and f-ups – Why they’re critical and how to learn from them

Last May, I spent $10,000 on a research trip to New York for a book concept that I ultimately ditched. The trip was a bit of a train wreck, and culminated in a hot mess of panic attacks in a New York hotel room, a deep dive into a depressive episode and a humiliating gash in both my wallet and my ego.

But I learnt more about myself and how to succeed as a result of this momentous failure than I ever have from all the breezy successes in my life. This f-up got me questioning EVERYTHING. It led me to examine aspects of myself I’d never dared to previously.

It’s not all unicorns and sunshine when you fail. There’s pain. In my case with this trip, a truck load.

But I’m wiser as a result of my failed book research trip. Softer, yet stronger somehow.  I’m certainly clearer about my purpose than I’ve ever been before. My New York Non-Accomplishment made me a better executive coach. I’m more compassionate with those who are struggling and I have a greater understanding of what it’s like to suffer.

These days, I’ve learnt to let my values lead my book writing, rather than any misguided desire to prove myself worthy enough (in whose eyes I’m not sure).

If you want to be a successful leader, get comfortable with the discomfort of failing.

Anything worthwhile you’ve mastered in your life has seen you flounder long before you flew.  Anything important you’ve discovered about yourself probably followed a botch-up or misstep of some kind or another. This is also the case with the people you lead.

According to new research from a pair of economists from Stanford and the University of Michigan (Francine Lafontaine and Kathryn Shaw), failed entrepreneurs are far more likely to be successful in their second go-around, provided they try again.

It’s what we do with failure when it happens, that counts.

Here are six ways you can develop a healthy relationship with failure:

1. Respond, don’t react to your mistakes. Notice your initial emotions like anger, fear, or shame. Being aware of our own emotions is a critical component of emotional intelligence. Ask, “what is needed most right now?” and “what are the lessons to learn from this?” Non-judgemental and curious are the vibes you want to channel when it comes to stuff-ups – yours or others. Failure can teach us not only where we’re going wrong, but how to do it right next time. Was the failure due to process, people or something else? With my book research trip, I knew I had a great idea, it was just that the book was not mine to write. When I stopped beating myself up and got curious, profound lessons emerged.

2. De-stigmatise failure (especially first-time failures) by being loud and vocal about the learnings. This is great for creating psychological safety and trust in the team you lead. Formally support learning from mistakes by instigating regular reflection and review of projects, especially using data-driven approaches.
3. Structure projects to allow for some experimentation and ‘small’ failures. ‘Ooch’, as Heath and Heath espouse in their clever book, Decisive. ‘Ooching’ or running a pilot test allows you to test your theories. Rather than jumping straight into a thing boots n all, we dip our toes in. This way, failures won’t bring the company down in one fell swoop. Rather, ‘ooching’ lowers the impact of mistakes and provides insights associated with those experiments. If I’d taken my own advice here, I’d have saved my bank account a big blip. A trip to the East Coast rather than New York might’ve been more the way to go.
4. Adopt a growth mindset towards yourself and those you lead.  When you go to praise someone, focus on their effort, rather than their skill or intelligence. For example, “I noticed you put a lot of effort into getting that project delivered on time and it made a huge difference to the result.” As opposed to – “you did well, you’re really good at these types of projects.” Carol Dweck’s research shows people are more inclined to try new things when a growth mindset is adopted i.e. praising for effort. Conversely, people stay within their comfort zones when praised for intelligence.
5. Model what you want to see in others. ‘Failure tolerant’ leaders openly admit their mistakes rather than covering them up or shifting the blame.  Developing a healthy and productive relationship with failure starts with the person in the mirror. If you see failure as an inherently bad thing, your team will pick this up, regardless of what you might say. Admit your goof-ups publicly (especially with those you lead) and highlight the insights and changes you’ll make as a result of those failures.
6. Tolerate failure but address repeated mistakes and patterns. Looking closely at the root cause of failure helps determine the ‘good mistakes’ from the ones we want to stamp out quick smart. The same mistake made over and over without course correction requires decisive action. As does ethical transgressions. Powerful questions and analysis of root causes through a combination of data analysis and intuition helps you ace this process.

It still stings my ego and brings a squirmy lurching in my gut to think about my New York trip. But I don’t regret it one bit. I’m even grateful for the ass kicking it gave me. I’m learning to greet failures as ‘detours in the right direction.’

What’s a failure you’ve made in your leadership journey and what did it teach you? Share your story.