What Went Wrong And How Can I Learn From It?

The role of leadership in learning from failure.

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“If you never know failure, you will never know success.” — Sugar Ray Leonard —

I’ve been contemplating failure a lot lately. Last year was an intense one and though a lot of things went right and I leveled up on many fronts, I didn’t walk through the fire unscathed and I made a lot of mistakes in the process.

But here’s the thing: many change makers and thought leaders attribute failure with propelling them to greatness. Each time life knocked these individuals down, they got back up, dusted themselves off and moved forward, forever changed by the lessons learned from what we would call “failure”. And they got better. But not just better. Over time they got excellent. Because they used failure as a springboard which, combined with hard work, because make no mistake, learning from failure is hard work, allowing them to go further and faster than they previously would have been able to.

‍In her article Why learning from failure is the key to your success Madeline Miles argues that learning from failure helps cultivate mental toughness and resilience (which are also precursors to learning from failure). As Ernest Hemingway so eloquently put it, “[t]he world breaks everyone, and afterward, some are strong at the broken places.” But you only get stronger if you take advantage of the lessons that failing presents — and that requires a paradigm shift to re-frame how we see failure.

I’ve written about the role that self-love played in helping me understand the mistakes I made as a precursor to learning from them. I believe that self-love, rather than self-flagellation, in the aftermath of failure is essential to learn all the lessons our mistakes can teach us. But that alone is not enough.

Re-framing failure

‍In order to learn from failure, we need to see it as a teacher and that requires a re-think of how we frame failure in our own minds, within our organizations and in our societies. While failure has gotten a makeover recently, many of us continue to have negative associations with the concept. Everyone wants to succeed. Nobody wants to fail. Yet, it is impossible to succeed without failing. This is the conundrum we are faced with as humans.

Unfortunately, many of us have been brought up to think failure is bad, especially through the current neoliberal idea of failure and success now entrenched in education systems and societies. But if you look at traditional wisdom around the world, failing is a part of life and an opportunity to expand and stretch to achieve what was previously thought impossible. In a recent article on failure Roshana Ariel wrote that failure can also be fun and is a “one of the most enjoyable parts of the journey” to success (whatever success might mean to you).

However, we still need to get beyond our negative perceptions of failure to see it as part of a well lived life. In her paper entitled Strategies for Learning from Failure in Harvard Business Review professor Amy Edmondson makes a compelling case for reframing failure, arguing that:

small process failures are inevitable. To consider them bad is not just a misunderstanding of how complex systems work; it is counterproductive. Avoiding consequential failures means rapidly identifying and correcting small failures.

At the end of the day failure means you are trying new things and if you’re not failing, you’re not really living. To live a full life you have to have courage to fail. If we could all revel in failure our lives would transform and we would have the courage to fundamentally transform the lives of others. Martin Luther King, Jr. articulated the importance of seeing challenges in our lives as opportunities to meet ourselves when he said:

The ultimate measure of a [person] is not where [they] stand in moments of convenience and comfort, but where [they] stand at times of challenge and controversy.

When we dare to dream big, failure must become our friend, our constant companion on the journey to a new life, a new world.

Understanding failure

Before we learn from failure, we must first understand how we have failed and that requires understanding the different types of failure. Edmondson maintains that failures or mistakes generally fall into three categories: preventable, complexity-related, and intelligent.

Preventable failures are fairly self-explanatory in that they could have been avoided quite easily. If these types of failures are occurring with regularity then there is something wrong with the system or someone might just be overwhelmed. I made preventable failures quite frequently last year in the midst of extreme overwhelm.

This year I’ve committed to doing less multi-tasking. I’ve been telling myself for a long time that I’m good at multi-tasking. Last year I finally realized that I’m really not. And I’m not sure anyone is. I’m doing less this year but doing it better and making more time for me. I’ve already seen a huge leap in what I’m able to do each day simply by being less overwhelmed.

‍Unavoidable failures in complex systems occur in uncertain situations with combinations of issues, actors, systems among other variables that have not occurred before. Edmonson maintains that while significant failures can be avoided by understanding best practices and ensuring systems are in place to analyze issues as they occur, some failures are inevitable in new situations.

Convening regular conversations about what is going well and what could be better will help us navigate this new territory and chart a path forwards. Sharing those lessons is critical for ensuring we can learn from the failures of each other and avoid common pitfalls. Deep listening, reflecting and learning is critical. A broader and alternative perspective of the problem also broadens the mind to the possibilities and creation of innovative solutions.

The last type of failure Edmondson identifies is intelligent failure at the frontier. This type of failure occurs when experimentation or innovation is necessary because new ground is being broken (i.e. something hasn’t been done before). Experimentation done right can produce results quicker through intelligent failure. This type of failure requires creating environments that support and drive innovation and that requires strong leadership.

Optimizing learning from failure

While failure is inevitable, learning from it is unfortunately not and without learning from our mistakes we will continue to repeat them. Researchers Laura Ekreis-Winkler and Ayelet Fishbach remind us of the complexity of learning from failure in their paper You Think Failure Is Hard? So Is Learning From It. If you can’t access the paper it is very well summarized in an article by Noam Shpancer.

In their paper Ekreis-Winkler and Fishbach argue that there are two primary reasons why people and organizations fail to learn from failure. The first reason is emotional. Humans tend to want to feel good about themselves and as such do not want to contemplate failure. If we don’t cultivate self-love we will be more likely to confuse our mistakes with who we are. And that could send us down a shame spiral, a phenomenon which Brené Brown has studied and written about extensively. In order to avoid feeling shame, we avoid thinking about our failures. In his article The smart way to learn from failure, David Robson calls this the “ostrich effect”.

‍The second type of failure is cognitive in nature and reflects a confirmation bias whereby humans tend to seek out information that aligns with their belief systems. Again, we don’t want to contemplate failure. Another cognitive reason for not learning from failure according to Ekreis-Winkler and Fishbach is because it’s difficult and requires a lot of self-reflection, both as individuals and as organizations. Unfortunately, both increase mental discomfort and limit the creative capabilities of the human mind over time.

‍A strategy for overcoming cognitive barriers is to allow others to do what Shparcer calls the “heavy cognitive lifting” for us by demonstrating the lessons in particular failures and providing information that will help avoid similar mistakes in the future. One way of doing this might be to have regular discussions to unpack failures during which team members are encouraged to reflect on their own mistakes and that of the team as a whole. The goal would be not to assign blame but rather to discuss how to learn from mistakes. Avoiding the “blame game” is essential to learning from failure and this requires strong leadership. Edmonson argues that:

‍Strong leadership can build a learning culture — one in which failures large and small are consistently reported and deeply analyzed, and opportunities to experiment are proactively sought. Executives commonly and understandably worry that taking a sympathetic stance toward failure will create an “anything goes” work environment. They should instead recognize that failure is inevitable in today’s complex work organizations.

‍In their book Extreme Ownership former Navy Seals Jocko Willink and Leif Babin argue that leaders must take responsibility for everything that happens within the teams that they lead. When leaders take extreme ownership of failure they take the blame out of the game and allow for an intellectual exercise which encourages learning from failure. Edmonson argues that the goal should be to build a culture that makes it safe to admit and report mistakes.

Certainly, leadership within organizations is essential but so is leadership across institutions to create an environment in which actors both within and across communities of practice exchanging lessons learned and share failures regularly.

As individuals each of us has a role to play in ensuring that we learn from failure. In her article Miles argues that there are five ways in which we can ensure that we learn from failure:

1. Persist despite failures: This requires grit which is an essential element to success;

2. Adopt a growth mindset in which challenges are embraced and failure is used to learn, grow and get better;

3. Practice inner work which can include meditation, mindfulness, journaling, walking in nature — whatever works for you;

4. Be courageous: Doing anything new requires courage and that will require being kind to yourself and understanding that failure is inevitable. The only way not to fail is not to try;

5. Build mental fitness within yourself and your team by promoting social connections and physical health;

In her article Miles shares a link to a video of a four year old girl snowboarding down a hill with her dad which includes her verbal commentary along the way (and how cute is she in her dinosaur costume?). The little song she sings to herself includes the line:

I won’t fall. Or maybe I will. But that’s okay because we all fall.

‍Clearly, that little girl’s parents have cultivated an environment in which she feels like it’s safe to try new things because “we all fall”. And she’s a pretty decent snowboarder at four years old.

‍Building a culture in which learning from failure is optimized requires that we focus on what’s going well much more than reflect on what has gone less well. In our teams we must celebrate our wins daily, weekly, monthly and yearly and congratulate each other often.

Being proud of what we have accomplished and finding joy in the day to day is integral to cultivating a healthy environment and a healthy team (because the first is necessary for the second) with a collective growth mindset. From there, learning from failure becomes an adventure because you know it’s an opportunity to get even better.

This article is an excerpt from a blog I wrote on why we need to fail forward in our work as change makers with my colleague and friend Kehinde Balogun. You can find it here.

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