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Facilitating Learning Through Failure

Too often, I have observed senior team members and project leaders jump into problem solving sessions straight away, helping the team or team members solve challenges as soon as they appear. This approach, while most certainly motivated by a desire to help and serve the team, actually does the opposite, robbing the team of precious opportunities to experiment and grow. I am hoping to explain a framework that is easily understood, that will allow leaders to more properly gauge when and how to support the team, not only to produce successful projects, but also to maximize the opportunity to learn. This simple framework will lead to better products, happier teams and better organizations that get stronger over time.

In the Agency and Startup worlds we hear a lot of quotes around the power of failure:

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

“If you’re not prepared to be wrong, you’ll never come up with anything original.” - Ken Robinson

“Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end. Failure is something we can avoid only by saying nothing, doing nothing, and being nothing.” - Denis Waitley

Inspiring, right? But what if we aren’t talking about trying to change the world or achieve greatness? What if we are talking about the innumerable commonplace challenges our teams face every day? The, “How can we increase our velocity?” or “How can we accelerate client approvals?” types of questions that are routine in software development. The right amount of failure is a good thing and leads to learning. Too much though can cost agencies clients, or employees their jobs. How can we help our team members find the sweet spot? How do we know when to offer coaching, versus stepping in with solutions, versus doing nothing but observing and offering words of encouragement? The answer lies in understanding what motivates our team members, coupled with the ability to recognize their collective level of engagement with each problem space. Once you understand those two things, it becomes more straightforward to determine when and how to get involved.

A Quick Caveat

Briefly, let’s talk about project timelines and milestones and get that out of the way. As team leaders our number one priority is to protect our team, part of which means helping make sure their projects are delivered successfully. If the team or team member’s time spent experimenting is putting the success of the project at risk, it is perfectly acceptable to help accelerate progress towards a solution by contributing to the discussion, even at the cost of the team learning valuable lessons. This is a time when direct participation is required and expected of leaders with the most experience. It doesn’t mean that you become a dictator, but this is the time when you should share your input thoroughly on what you think is the best approach. There will be ample opportunity for everyone to learn again tomorrow. A properly designed project plan will incorporate time for learning and experimentation so if you find yourself needing to jump in early and often in order to keep things on track, you might consider re-evaluating your project planning approach.

Understanding Motivation

In his book, Drive: The Surprising Truth About What Motivates Us, Daniel Pink writes, “The science shows that the secret to high performance isn’t our biological drive or our reward-and-punishment drive, but our third drive—our deep-seated desire to direct our own lives, to extend and expand our abilities, and to make a contribution.” Self directed contribution is the key. The science tells us that if we make space for people to try to solve problems, they will, because they are intrinsically motivated to do so. People generally don’t want to just be given the answers, to execute upon other’s visions without room for their own contributions. People need to experiment in order to be genuinely happy and fulfilled. As long as we nurture that tendency and provide a psychologically safe environment, the team’s natural tendency will be to experiment.

Fostering Engagement

Once we understand that as long as we provide the right environment people will naturally tend to experiment, we can turn towards trying to maximize the learning that comes from it. This is where engagement comes into play. A clue for how to manage this properly comes from Mihaly Csiksentmihalyi as explained in his book, Flow. Being in “Flow” is described as being fully immersed in the activity at hand, to the point where one loses track of time. The activity becomes the entire focus. We have all had the experience of flow while doing things that we enjoy. If you have ever uttered the phrase, “wow time just flew by!”, you were just in flow. Flow can be something you do by yourself in quiet, or with a group while active. Academics might be in flow while performing research in a library, while a professional basketball player might be in flow out on the court during the big game. The key to remaining in flow, Csiksentmihalyi explains, is that the team should be of the appropriate level of skill and the problem should not be too hard or too easy. If the work falls into this “goldilocks” zone, people will stay engaged, in flow, for longer.

Therefore, there is really only one thing that we need to pay attention to, to tell us everything we need to know in order to help the team progress. Are they fully engaged? Are they offering up ideas, collaborating and riffing, enjoying themselves and working the problem? If yes, then you are in a good place to let the experimentation continue. They are learning from their mistakes just by doing, as explained in this story from the book Art & Fear by David Bayles and Ted Orland which demonstrates the power of failure:

The ceramics teacher announced on opening day that he was dividing the class into two groups. All those on the left side of the studio, he said, would be graded solely on the quantity of work they produced, all those on the right solely on its quality.

His procedure was simple: on the final day of class he would bring in his bathroom scales and weigh the work of the “quantity” group: fifty pound of pots rated an “A”, forty pounds a “B”, and so on. Those being graded on “quality”, however, needed to produce only one pot – albeit a perfect one – to get an “A”.

Well, come grading time and a curious fact emerged: the works of highest quality were all produced by the group being graded for quantity. It seems that while the “quantity” group was busily churning out piles of work – and learning from their mistakes – the “quality” group had sat theorizing about perfection, and in the end had little more to show for their efforts than grandiose theories and a pile of dead clay.

Knowing How and When to Step in

How the team is engaging will guide you as to how to tailor your contribution to the conversation. If they are rapid firing ideas and you can see that multiple people are waiting for the chance to speak, as a leader we don’t need to do anything but be present and enjoy the moment. If they are engaged but struggling to agree or can’t seem to get started generating ideas, consider facilitating a brainstorming exercise of some sort. (Bear in mind that sometimes introducing a fun activity for 20 - 30 minutes before coming back to the problem can also spur creativity by giving people’s subconscious time to work.) If they are still struggling for ideas this is where hints, posed as questions that could yield more fruitful lines of thinking can be leveraged.

Finally, if you see engagement start to lag, people aren’t speaking up, body language seems more tired, less smiles, jokes and laughter, then it is perfectly fine to start offering your own solutions. Be on the lookout though, if after dropping some ideas the team becomes re-energized and starts flowing again, by ready to slip back into the background and resume observing.

Good organizations deliver quality products or services for their customers. Great organizations deliver that same quality while also providing an environment that keeps their team members happy. The best organizations do both while also providing ample opportunities for people to grow and learn, professionally and personally. This is where making room for failure can become a game changer for you and your team. Providing a safe space for experimentation and failure, will lead to better product outcomes and happier team members. Give the above ideas a try and before you know it, you and your team will become an unstoppable creative force that joyfully tackles any challenge.

“The joy is in the pursuit more than the realization. In the end, mastery attracts precisely because mastery eludes.” ― Daniel H. Pink, Drive: The Surprising Truth About What Motivates Us

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