We can learn to be lucky

Learning only when we make a mistake is not enough.

Life is too hard. Creating value in enterprises is too hard. Marriage is too hard. Reaching goals and making our dreams come true is too hard. All these aspirations are too hard to only learn some of the time.

Some people say we learn more from failures than from successes, and that may or not be true. But the way I see it, that’s a misleading trade off: we can learn a lot from both.

However, what I’ve observed in organizations is that in practice teams usually learn much less from successes than from failures. It’s not that they can’t learn more, they just don’t.

This is for two main reasons. First, teams usually have less motivation to learn from success - why be a downer and interrogate our victory when we could be celebrating? Even when teams choose to debrief successes, they seem less willing to be introspective and self-critical so the debriefs they do are less fruitful. Moreover, most organizations have more systems that force debriefs of mistakes to happen.

The second reason why teams tend to learn less from success is a matter of technique. Learning from failure is a bit more familiar because it’s an exercise of cause and effect. We saw bad effects, and the goal of a debrief is to understand the root causes. By understanding the root causes we can make different choices in the future.

Learning from success is different (and perhaps harder) because it’s an exercise of understanding counterfactuals. What could we have done to obtain a better result? What aspects of our success were because of our decisions and skills, rather than good circumstances? The fundamental questions when trying learn from a success are different than those needed to debrief a failure.

When you’re doing your next debrief, try these three questions to get the most learning possible out of a success. I’ve included some rationale for the questions and some examples within each.

Question 1: What would’ve had to be true to have a 2x better result? What about a 5x or 10x better result?

This question helps us understand the money we left on the table. If we were successful it means we already had some level of competence or skill related to the challenge at hand. Could we have done better? Why didn’t we? Are we at a plateau of performance? How can we break the plateau and get to the next level? This is what this question gets at.

I thought about this question a lot when working on violence prevention programs at the Detroit Police Department. There were quarters and years where we had substantial drops in shootings and murders. A lot of time that was because the community-based gang violence prevention programs we launched were working. But in Detroit, even after those successes, violence wasn’t at an acceptable level for our team, our leadership, or our community.

When we asked questions like, “why can’t have a 30% drop instead of 10% drop” we thought about other avenues for reducing violence. We started to explore domestic violence prevention, partnerships with social service organizations and faith-based organizations, and other non-traditional avenues. Thinking critically about our success helped us to lean in harder to the problem.

Question 2: What was a near-miss? What almost was a big problem but we got lucky?

This question helps us understand where caught a break. Teams generally discount their own luck, and do so at their own peril. Because the next time around, we might not be so lucky.

I just experienced this at Thanksgiving. Our family’s tradition is to go to the Detroit Lions’ Thanksgiving Day football game, and we host an early brunch at our house since we live closest to Downtown Detroit where the stadium is. I make bagels & lox, a breakfast casserole, and coffee. My father-in-law makes bloody marys.

When he arrived, he asked, “do you have ice?”

We usually do not have ice in our house. Our refrigerator is old, and doesn’t have a built-in ice machine. But this Thanksgiving, we were lucky - we happened to have extra ice in the freezer from a party we hosted a few weeks earlier.

Even though our family brunch was a resounding success, I learned something important: make ice part of the plan for any party. I added “get ice” to the party prep checklist I keep on my phone. I also plan to look into a better set of ice molds to make it easier to have ice on hand all the time.

Question 3: What gifts were just handed to us that we did nothing to earn?

This question helps to understand and shape luck. Teams usually have some headwinds or beneficial circumstances that just fall into their lap without even trying. Usually, those headwinds aren’t a guarantee for future challenges. But if we understand what made us lucky this time around, we can actively try to shape those headwinds in the future.

I saw this happen on a project some of my colleagues recently completed. It was a data analysis to understand a large area of SG&A for our company. The project was a clear success because the insights uncovered will have a huge benefit for our company and our customer. By all accounts the team did a great job and they executed flawlessly.

But they did have a healthy amount of luck, too. The executive sponsoring the project had an incredibly clear and specific question they wanted to understand. The clarity the team received up-front led to a very focused analysis on a specific set of data. Many times people who request work of analytical teams have no idea what they actually want to understand, and that creates huge drag on an analytics team.

It was a big headwind to have a clear, and focused question from jump. That’s definitely not a given on any project. But what we learned is that in the future we can push for clarity and actively shape the question very early in any analytics project to create headwinds for the team. We can shape our own luck.

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Every team and every organization I’ve been part of underperforms. Even the best teams out there have even higher ceilings. We can and should learn from failures, but we can learn just as much from successes with the right questions and approach. And if we do that, we can learn to be better and contribute more to our teams, our customers, and our communities.

Photo credit: Unsplash @glambeau