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

Salsa is the last stage of grief

To many of my oldest friends, my father was best known for one thing: his salsa.

It was objectively out of this world, and the craftsmanship he used was nothing short of incredible. I remember watching him, at the green granite island in my childhood home, taking tomatoes and looking at them like a championship athlete surveys a playing field.

Then he’d take these tomatoes and mince them into minuscule cubes, better than a machine could, even if he had a dull knife. Then he’d do the same with an onion and cilantro before adding spices, hand-squeezed lime juice, and one or two green chilies. His salsa was the stuff of childhood legend, and the way he made it, with such precision and pride, was legendary to me.

It is without exaggeration to say that one specific thing I grieved when he went ahead was that I was never able to have an afternoon with him - where he would pass on the recipe, yes, but also his wisdom, his blessing, and the torch. Even when I was young, long before I knew he would be taken from us so suddenly, I put it in my mind that the salsa was not just a recipe but an important rite of passage.

I haven’t been able to bring myself to try making it since he died. The thought of making it was sad, but also scary. The knife would’ve invoked the feelings of a haunted house, I thought, and how could I do it justice without him teaching me the secrets of his work? Anything less than perfection would’ve felt like an insult to his memory.

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My family has more than its fair share of gardeners.

I’ve been hearing about Udai Mama’s green thumb - he’s one of my four maternal uncles - from my mom for decades. My Masi, who’s know by her nickname “Gudda” in our family, is the same way. She’s created an Eden in her backyard in Long Island, with everything from tomatoes, to Indian vegetables, to figs.

She sent us home with a bounty from her garden last weekend, when we were visiting our New York family. So here I was, with a deluge of perfectly ripe tomatoes I didn’t know what to do with, which would surely rot within a week without intervention. And how could I waste a basket of tomatoes from my aunt’s garden? I may not be perfect, but I’m not a savage.

As it happened, five days after our return from New York, our youngest son Emmett was to be baptized. Our plan was to have everyone over - our family, godparents, friends, kids, everyone - for an early dinner before Mass. Robyn created the menu and had us stocked up to make our crowd-favorite white bean chili, cornbread, and a frosted chocolate cake. I picked up a Sister Pie because I happened to be in the West Village for lunch with an old friend.

And there were those tomatoes in the orange, plastic colander - the one Robyn had in her apartment when we first started dating - that were just sitting there, catching sunshine, getting riper and riper by the day.

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It was one of the proudest moments, Papa, I’ve ever had over something I’ve made - when person after person was raving about the salsa I made. Your salsa. I got to tell all our friends and family present for Emmett’s baptism - most of whom I met after I moved to college - the story of your salsa and say with so much joy, “I’m glad you liked it, it was my Dad’s recipe. I always thought he should market it, too.”

As I was making it, I was remembering you. I was remembering your life, how you left India and landed in Tehran to join the ship on which you were to be an engineer. I was remembering how intensely you insisted on doing the right thing, in the right way, down to how you impressed upon me, “You MUST cut the tomatoes by hand, a machine leaves the pieces too large and soft. The tomatoes must be firm, Neil, FIRM.”

When you died, in addition to tremendous sadness and grief, I was also under duress for practical reasons. I didn’t know how to do any grown up stuff.

How do I negotiate a salary? How do I buy a house or plant a garden? How do I feed a baby a bottle? How would you like your last rites to be conducted? How do I find a new dentist? How do I file my taxes? How do find my way in life? How do I make your salsa? These were the things I needed to ask you, that I never could.

And beyond those practical concerns, that was supposed to be our time. I was finally grown. We could finally be the friends we were always meant to be. Asking you for advice was how we were going to bond as grown men.

I was so sad that we never got that time. I still am, because I’m balling as I’m writing this part of the essay. But I suppose you probably see that.

But a funny thing happened as I was making that first bowl of salsa yesterday. In addition to remembering you. I was remembering all the stuff that’s been going on over the past few weeks. All the grown up stuff Robyn and I have had to do lately.

I took the lead for us and traded in Robyn’s car for a minivan that can fit our growing family. I cleared the garden we plotted in our backyard for the winter, and put away the drip irrigation system I installed. I found a masonry contractor and got our garage fixed. I found a high-interest cash account to take advantage of rising interest rates. I navigated a career decision. I, and Robyn too, figured out how to get help from a therapist-coach so we could be better parents to Bo - and we graduated, so to speak, after four months, earlier this week. I figured out that the secret ingredient I was missing in the salsa was ginger.

I realized when I was chopping those tomatoes and onions that you probably never had a salsa recipe. Of course you didn’t have a recipe. Indians didn’t invent salsa. You made it your own. You figured it out. Just like you figured out everything else in your whole adult life, when you were oceans away from your family, making it as a first-generation man in this country.

As I was squeezing the lime I remembered all the things I saw you figure out. How to make a shelf. How to deal with customer service agents who disrespected anyone with an accent. How to use credit card points toward the purchase of a car. How to build a house. How to deal with unemployment. How to raise a son. How to be an honest man. How to live a life.

You were the example of figuring it out, for my whole life, and that’s what I realized yesterday. Even though you went ahead, I should’ve never been worried about the things I didn’t know how to do. It was never about that. I finally realized that you never needed to teach me the salsa recipe or anything else fathers tend to teach their sons as adults. Because you taught me to figure it out. You left me prepared, long before you died, to figure it out - whether it was the salsa or anything else.

It was an unexpectedly big moment, Papa. I’m not scared anymore. I can figure it out. I know this now.

I can figure out how to build a thriving marriage. I can figure out how to be a father to each of our very different sons. I can figure out how to be a man of good character, worthy of our family’s name. I can figure out how to make a contribution to this world, in my job and outside of it. I can figure out how to make your salsa, because you taught me to figure it out.

It’s a cliche to say, but is true - not a day goes by where I don’t think of you. I’m still so sad that you can’t be here with us for the big and little family moments we have. I still have so much gratitude and joy when I think of the happy stories we can tell about you. I know you would’ve wanted us to keep living life, and I swear to God I have. But the weight of grief has been heavy.

But yesterday was a big moment. Something feels different, lighter perhaps. When I think of you I will always have sadness, gratitude, joy, and laughter all mixed together. But now, after learning this lesson from the salsa, the grief part might now, finally, be over.

Photo Credit: Unsplash @yehoshuaas

Learning to Win Ugly

What it takes to “win” is different than what it takes to “win ugly.” In sports what it means to win ugly can be something like:

• Winning a close, physical game

• Winning in bad weather or difficult conditions

• Winning without superstars

• Winning after overcoming a deficit or when your team is particularly outmatched

• Winning by just doing what needs to be done, even if it’s not fancy or flashy

But winning ugly is also a useful metaphor outside sports:

• In a marriage: keeping a relationship alive during adversity (e.g., during a global pandemic) or after a major loss

• In parenting: staying patient during bedtime when a child is overtired and throwing a tantrum

• In public service: improving across-the-board quality of life for citizens after the city government, which has been under-invested in for decades, goes through bankruptcy (I’m biased because I worked in it, but the Duggan Administration Detroit is my thinly veiled example here)

• At work: finding a way to reinvent an old-school company that’s not large, prestigious, or cash-infused enough to simply buy “elite” talent

The point of all these examples is to suggest that it’s easier to succeed when circumstances are good, such as when: there’s no adversity, the problem and solution are well understood, you’re on a team of superstars, or you’re flush with cash. It’s something quite different to succeed when the terrain is treacherous.

I’ve been thinking about the idea of winning ugly lately because as a parent, the fee wins we’ve had lately have been ugly ones.

Generally speaking, I’ve come to believe that winning ugly is important because it seems like when the stakes are highest and failure is not an option - like during a global pandemic, or when a city has unprecedented levels of violent crime, or when the economy is in free fall, or a family is on the verge of collapse after a tragedy - there’s usually no way to win except winning ugly.

I’d even say winning ugly is essential - because every team, family, company, and community falls upon hard times. In the medium to long run, it’s guaranteed. But honestly, I don’t think most people look at this capability when assessing talent for someone they’re interviewing for a job, or even when filling out their NCAA bracket. 

Moreover, as I’ve reflected on it, I’ve realized that my whole life, I’ve been coached, actively, to avoid ugly situations. I was sent to lots of enrichment classes where I had a lot of teachers and extra help to learn things (not ugly). I had easy access to great facilities, like tennis courts, classrooms, computer labs, and weight rooms (not ugly). I was encouraged to take prep classes for standardized tests (not ugly). I was raised to think that the way to achieve dreams was to attend an Ivy League school (not ugly).

If I did all these things I could get a job at a prestigious firm that was established, and make a lot of money, and live a successful life.

What I’ve realized, is that this suburban middle class dream depends on putting yourself in ideal situations. The whole strategy hinges on positioning - you work hard and invest a lot so you can position yourself for the next opportunity. If you’re in a good position, you’re more likely to succeed, and therefore set yourself up for the next thing, and so on.

If you don’t think winning ugly matters, this is no problem. But if you do believe it’s important to know how to pull through when it’s tough, the problem is that the way you learn to win ugly is to put yourself into tough situations, not easy ones. The problem with how I (and many of us) were raised is that we didn’t have a lot of chances to learn to win ugly.

I, for example, learned to win ugly in city government, at the Detroit Police Department…in my late twenties and thirties.

There, we caught no breaks. Every single improvement in crime levels we had to scrap for. Every success seemed to come with at least 2 or 3 obstacles to overcome. We didn’t have slush fund of cash for new projects. We didn’t have a ton of staff - even my commanding officers had to get in the weeds on reviewing press briefings, grant applications, or showing up to crime scenes. Just about any improvement I was part of was winning ugly. 

By my observation here’s what people who know how to win ugly do different:

No work is beneath anyone: if you’re winning ugly, even the highest ranking person does the unglamourous work sometimes. You can’t win ugly unless every single person on the team is willing to roll up their sleeves and do the quintessential acts of diving for loose balls, grabbing the coffee, sweeping the floor, or fixing the copy machine. 

Unleashing superpowers: If you are trying to win ugly, that means you have to squeeze every last bit of talent and effort out of your team. That requires knowing your team and finding ways to match the mission with the hidden skills that they aren’t using that can bring disproportionate results. People who win ugly doesn’t just look for hidden talents, they look for superpowers and bend over backwards to unleash them.

Discomfort with ambiguity: A lot of MBA-types talk about how it’s important to be “comfortable with ambiguity”. That’s okay when you have a lot of resources and time. But that doesn’t work if you’re trying to win ugly. Rather, you move to create clarity as quickly as possible so that the team doesn’t waste the limited time or resources you have.

Pivot hard while staying the course: When you’re winning ugly, you can’t stick with bad plans for very long. People who have won ugly know that you don’t throw good money after bad, and you change course - hard if you need to - once you have a strong inclination that the mission will fail. At the same time, winning ugly means sticking with the game plan that you know will work and driving people to execute it relentlessly. Winning ugly requires navigating this paradox of extreme adjustment and extreme persistence.

Tap into deep purpose: Winning ugly is not fun. In fact, it sucks. It’s really hard and it’s really uncomfortable. Only people who love punishment would opt to win ugly, 99% of the time you win ugly because there’s no other way. Because of this reality, to win ugly you have to have access an unshakeable, core-to-the-soul, type or purpose. You have to have deep convictions for the mission and make them tremendously explicit to everyone on the team. That’s the only way to keep the team focused and motivated to persist through the absolute garbage you have to sometimes walk through to win ugly. Teams don’t push to win when it’s ugly if their motivation is fickle.

Doing the unorthodox: People who can win pretty have the luxury of doing what’s already been done. People who win ugly don’t just embrace doing unconventional things, they know they have no other choice.

Be Unflappable: I’ve listed this list because it’s fairly obvious. When it’s a chaotic environment, people who know how to win ugly stay calm even when they move with tremendous velocity. This doesn’t necessarily mean they don’t get angry. In my experience, winning ugly often involves a lot of cursing and heated discussions. But not excuses.

Sure, I think it’s possible to use this mental model when forming a team or even when interviewing to fill a job: someone may have a lot of success, but can they win ugly?

But more than that, I am my own audience when writing this piece. I don’t want to be the sort of husband, father, citizen, or professional that only succeeds because of positioning. At the end of my life, I don’t want to think of myself as someone who only succeeded because I avoided important problems that were hard.

And, I don’t want to teach our sons to win by positioning. I want them to succeed and reach their dreams, yes, but I don’t want to take away their opportunity to build inner-strength, either. This is perhaps the most difficult paradox of parenting (and coaching at work) that I’ve experienced: wanting our kids (or the people we coach) to have success and have upward mobility, but also letting them struggle and fail so they can learn from it, and win ugly the next time.