Confronting Despair, Building Muscles, and Saving Democracy (and the World)

For the past 18 years, I have begun almost every introductory conversation about my work with the following questions:

  • What was your best experience collaborating with others?
  • What would your life be like if all of your collaborative experiences were at least as good as your best?
  • What would the world be like if everyone's collaborative experiences were at least as good as their best?

People’s reactions are fascinating. Some respond quickly with great stories. Most do not. Many seem to find it easier to think of stories from their personal rather than their professional lives. Everyone finds it easier to come up with terrible experiences than with great ones.

We all want to live in a world where our experiences working and being with others feel vibrant, productive, and meaningful, where we feel more capable and alive with others than we do by ourselves. I believe that this world is possible. It’s why I do what I do. Most people with whom I come across don't share this belief, and I can understand why. If it's so difficult to come up with one great experience collaborating with others and if most of your experiences collaborating with others are terrible, why would you believe in the collective potential of groups?

Belief. This is where the work has to start.

All the Bad Things

My friend and colleague, Travis Kriplean, had his first kid three years ago. As with many of my friends, impending parenthood caused him to reflect about the world he was bringing his son into and what he could do to make it better. As part of that, he began a deep inquiry into the impending planetary crisis we find ourselves in.

As Travis started to emerge from his inquiry, he pulled together a reading list and started organizing one-on-one discussions with friends, including me, to help him make sense of what he was learning. I read each of his carefully curated items over the course of a few weeks, then we talked for over two hours about the readings. I happened to be in the middle of my own little experiment around sensemaking, and as part of that, we both agreed to draw and share a picture that somehow represented what we had heard and felt from our conversation. The following day, Travis sent me his picture of our conversation. He had taken my vision image that’s on the homepage of this website and performed a cheeky (and accurate) cut-and-paste job:

As was clear from his reflection of our conversation, I had been completely demoralized by the readings and our conversation. The day after we talked, as if to punctuate the all-too-likely doomsday scenarios we had discussed, San Francisco became engulfed in a smoky haze from the Camp Fire, which ended up becoming the deadliest and most destructive wildfire in California history. The filthy air enveloped us for two weeks, reminding me that blue skies and breathable air might soon become a thing of the past.

What made it worse was that I wasn’t exactly starting from a place of cheeriness to begin with. Watching intolerance, white supremacy, and isolationism become normalized, even celebrated, all over the world has been disheartening to someone whose mission for the past two decades has been to increase self-awareness and empathy, to encourage critical and systemic thinking, and to find healthier ways to lean on each other for the benefit of all.

For the past three years in particular, I’ve spent a lot of time wondering whether I’ve been doing the things I need to do to move the needle on the world I want to live in, or whether I’ve been fooling everyone, myself especially, peddling false hope, smoke, and mirrors. It’s been a tortuous process, and I’ve made many changes as a result.

Despite all of this, I still believe.

Forgetting

Twenty years ago, when I was in the gestation period that would put me on my current path, I learned something interesting about Benjamin Spock, the famed pediatrician and author of The Common Sense Book of Baby and Child Care, first published in 1946. For 50 years, Spock’s book was the number two best-seller in the world. (Number one? The Bible.)

I found this startling. How could this be? Humans have been around for thousands of years, and we’ve been parenting that whole time. We have a lot of practice and experience and wisdom to build on. Why would we suddenly seek validation and knowledge from this one person about something we’ve been doing for so long and that’s so inherent to whom we are? Was Spock so much more insightful than anyone else about parenting? Was he better at explaining parenting than anyone else? Had we collectively forgotten how to parent?

As a child of immigrants, I am acutely aware of how easy it is to collectively forget. Like many immigrant kids of my generation, my parents taught me and my sisters English first, because they didn’t want us to speak with accents and they didn’t realize that it was easier to learn multiple languages when you’re young. Like many immigrant kids of my generation, I never ended up learning to speak my parents' native tongue, Korean.

When I was 14, my family went to visit my grandfather in Korea. He had not seen me since I was three years old, and he didn’t realize that I couldn't speak his language. As soon as we arrived, he asked me to come into his room to speak with me privately. He then started asking me questions in Korean. I felt disoriented and ashamed as I tried to explain to him in English that I didn’t understand him and as I watched his face shift from confusion to deep disappointment.

I never got another chance to speak to my grandfather, as he passed away the following year. It wouldn’t have mattered. I still can’t speak Korean, which means that I can’t speak to most of my relatives, I can’t read through old family letters and documents, and that so much of my family’s history and tacit knowledge will end with me.

It takes just one generation to forget, and the conditions for forgetting keep getting more optimal. Over the past century, families have separated and gotten smaller. Civic and community engagement have deteriorated (as Robert Putnam documented in his 2000 book, Bowling Alone), seemingly replaced in this day and age by clicks and swipes.

There was a time when we, as human beings, understood what it meant to thrive together, both in work and in play. We passed along the know-how and the rituals for generations. Now, it seems like we’re starting to forget. As our memories of what it means to be and thrive together wane, so does our faith.

On the one hand, the timing couldn’t be worse. On the other hand, maybe the popularity of Spock's work is simultaneously a sign of remembering as well as forgetting.

Remembering

In 1949, three years after Spock first published his book on parenting, the philosopher, Martin Heidegger, delivered a lecture entitled, "The Question Concerning Technology." In it, he argued that the essence of modern (i.e. post-Industrial Revolution) technology was to make us see everything — including each other — as things to be exploited and manipulated. Seeing and engaging in the world in this way resulted in us forgetting our humanity.

It’s a bleak essay, especially in the context of these times, but Heidegger does offer one tiny glimmer of hope. Toward the end of his lecture, he quotes the poet, Friedrich Hölderlin:

But where danger is, grows
The saving power also.

He then argues that the act of losing your humanity also makes you remember it, maybe even value it more. This awakening is a necessary (but not sufficient) first step in taking back what you’ve lost.

Heidegger’s framing of technology and humanity resonates with me on many levels. I think of it often when I think about my mentor, Doug Engelbart, who is the reason I'm in this business. Doug is most remembered for the long list of technology that he and his lab invented in the 1960s, including the mouse, graphical user interfaces, and hypertext. But Doug was never about inventing things. He was about lifting people up, about addressing the challenges that we were about to face, about augmenting our collective intelligence.

It took me a while to understand how radical and threatening these ideas were at the time. Most of the research in computer science in the 1950s and 1960s was focused on automating intelligence, replicating, even replacing humans, further validation of Heidegger's critique of modern technology. Doug was ridiculed, even reviled, but he was stubborn, and he was fortunate to have some visionary support in high places.

When I first met him in the late 1990s, it seemed like there was a large-scale awakening in society that had started happening, an appreciation of Doug's centering of people, which still felt radical, although perhaps no longer reviled. Still, he was scarred from those early experiences, and he continued to be troubled and depressed by how few people took his dire warnings about the future seriously. He passed in 2013, and I can't imagine how he'd be feeling if he were alive today.

Doug's commitment to his enormous vision was powerful, but that was not what ultimately had the most profound impact on me. What affected me most was how he treated me.

From the very beginning until the very end, he was curious about me, and he valued and cared about what he saw. When we first met, I was in my early 20s and hadn't accomplished anything of significance. None of that ever mattered to Doug. He treated me like a peer, and he cared about all aspects of me as a human being. I spent a lot of time wondering why he treated me so well and why he was so generous with me, before finally understanding that he treated everyone this way.

Imagine that. Doug treated everybody well, like they mattered, simply because they were fellow human beings. This impacted me more than any of his brilliant ideas, it's why I do what I do, and it's why I still believe. It seems so ridiculously simple and obvious, but I believe we've collectively forgotten how important it is, and more importantly, we're out of practice. If we start here, we have a chance. But we can't skip this step, because without it, we won’t remember how good it can be to be with others.

Practice, Hope, and the Trickle-Up Effect

Over the past few years, I’ve had the privilege of working with Sarita Gupta, who is not only a brilliant leader and organizer, but who also treats people the way Doug did. Before transitioning into her role at the Ford Foundation late last year, Sarita was the long-time leader of Jobs With Justice and Caring Across Generations, and had spent her entire career focused on the well-being of workers around the world. I spent a good amount of time with her and other progressive leaders trying to understand and help synthesize their visions and theories of change, so that they could see and explore where they were aligned.

Here’s what Sarita explained: Living with each other harmoniously, productively, and equitably at a national (or larger) scale doesn’t just happen, even when there’s structural support (which, for many people, there’s not). It requires lots and lots of practice to do it right. Trying to practice at a national scale is hard, perhaps impossible. However, it becomes viable and is just as valuable when we try it at a much smaller scale — with families, friends, community groups, schools, unions, the workplace, and so forth. When enough of us are leveraging these smaller spaces to practice, then we start to build collective power, a natural trickle-up effect starts to happen, and things start improving at a larger scale too.

Said another way, if we want to thrive collectively at a large scale, we need to start by learning how to thrive collectively at very small scales. When we ask each other, “What’s the best experience you’ve ever had collaborating with others?”, we need to be able to easily come up with stories. If we can do this, we will remember and believe. In these exceptionally challenging times, it’s hard to imagine anyone truly believing in democracy otherwise.

I already shared Sarita’s beliefs around the importance of practice and building “muscle,” but her overall framing has given me greater clarity and resolve around my own strategic focus. Specifically, we can have the impact we want on the larger world if we all start small, if we focused on spaces and groups in which we already have agency.

We can start with this simple principle, which Doug and Sarita modeled so well: Treat everybody well, like they matter, simply because they are fellow human beings.

When we invest in our personal relationships, we are building collaboration muscles necessary for a stronger democracy. When we invest in our own teams and organizations so that they have exceptional cultures where everybody brings their best and feel valued, we are building collaboration muscles necessary for a stronger democracy.

As we start to experience vibrant, productive, and meaningful relationships in small spaces, we will start to remember how powerful and wonderful it is to engage with each other collectively, which will inspire us to flex our collaboration muscles in all aspects of our lives. The more of us who start to do this, the more we will start to see larger-scale shifts.

This is how we will remember. This is how we will believe.

This is why I do what I do. This is why, despite all of the challenges we face today, I still believe.

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The Art of Aligning Groups

This essay is also available in French. Thanks to Lilian Ricaud for the translation!

My best experience collaborating with a group happened almost 20 years ago on a basketball court. I had just recovered from a back injury and was returning to my regular pickup game for the first time in two months. To my surprise, a bunch of new people had shown up that day, and I ended up on a team with four other guys I didn’t know.

It didn’t matter. That day, that game, we played the most beautiful basketball I had ever experienced. It was like a dance. No one was particularly great individually, but everyone knew how to play together. People moved without the ball, sprinting down the floor, screening and cutting. The ball barely touched the ground as we whipped it around to each other — dribble, dribble, pass, pass, pass.

We were playing fast, but I felt like I was seeing things in slow motion. I would pass the ball to empty spots, and the right guy would magically materialize just as the ball got there. Every basket we made was an easy basket, and we scored them in large quantities before finally putting the other team out of its misery.

The final score showed that we had collaborated effectively, but it didn’t tell the whole story. It didn’t say how it felt to play with that team, to be in flow with four other people, none of whom had ever played together before. Every movement felt effortless and joyful. I felt alive. The team felt alive.

Alignment Versus Agreement

People often ask how I measure effective collaboration. My answer is always, “It depends. What’s the goal?” Collaboration, by definition, is working together in pursuit of a shared, bounded goal. Whether or not you achieve that goal matters. However, how everyone feels in pursuit of that goal also matters. Success needs to take both of those things into account.

I think the word, “alignment,” conveys this nuance nicely by suggesting both directionality and movement. Alignment is dynamic. It’s irrelevant if the wheels in your car are in alignment if you’re not moving. Alignment is also not binary. If the wheels in your car are not perfectly aligned, you’ll still be able to drive. It just won’t be as smooth or as efficient as it could be. The level of resistance you experience is a measure of how aligned you actually are.

“Alignment” is not the same thing as “agreement,” although people often conflate the two. A group might verbally agree on a destination, but its participants might still move in conflicting directions. Conversely, a group might move in perfect lock-step without ever having explicitly agreed on where it’s going or how (as was the case in my pickup game). It might even achieve this while explicitly disagreeing.

This distinction is important, because it’s not necessarily hard to get a group to agree on something. One way is to make a statement that is so abstract, it’s both indisputable and meaningless. An example of something I often hear is, “We value collaboration.” Another one is, “Our goal is to better serve our customers.” Very few people would disagree with either of those statements, but by themselves, they’re too broad to mean anything. Agreement without alignment also often happens in groups with conflict-averse cultures, where people would rather assent than argue.

Being in alignment is different than moving in alignment. If the goal is for everyone to be moving toward the same goal in rhythm and without resistance, then everyone must both want to move in alignment with everyone else and be capable of doing this. You achieve the former by aligning. You achieve the latter by practicing.

How do you get a group into alignment? How can you tell when a group is aligned? And how can groups practice moving in alignment?

Alignment, Not Control

There is no one right way to get a group aligned. Sometimes, it just happens. More often than not, it takes work.

Most people seem to equate aligning as a top-down version of “getting buy-in.” In other words, someone — usually a person with positional power over everyone else — thinks really hard about the “right” way to do something, then tries to convince everyone else to go along with it with some combination of encouragement and threats, possibly integrating some feedback along the way.

This isn’t wrong, but it’s not the best way to motivate people, it doesn’t tap into a group’s full collective intelligence, and it doesn’t usually lead to great performance.

My philosophy with groups is that more perspectives lead to better outcomes. When it comes to goals and strategy in particular, rather than one or a few people coming up with their own ideas first and having others respond or comply, I want as many people as possible to think critically about the problem at hand and to co-create the solution. This is generally messier and slower (at first), because it requires people to align around language and worldviews and to struggle both individually and collectively. But that struggle leads to greater ownership and agency, which ultimately leads to higher performance.

Alignment obviates the need for control, but it requires stomaching the messiness of aligning. While the hallmark of moving in alignment is a feeling of flow, the process of aligning can feel exactly the opposite.

Building Alignment

What does a productive struggle look like? What does it feel like? How is it different from an unproductive struggle? How do you know how long to let it go?

The best I can offer are my own strategies for building alignment.

Ask and listen first. Give people a chance to think about something on their own first, even if you’ve already done a lot of your own thinking. If their thinking is aligned with yours, use their words, so that they see themselves in the work.

Write it down. We all lead busy lives. It’s easy to forget things, especially when they’re complicated. Capturing the state of people’s thinking, even when it’s messy, and constantly keeping it in front of them helps a group build on rather than reconstruct its thinking.

Put a stake in the ground. Stakes can be pulled out and moved, which means you don’t have to get it exactly right the first time. Don’t expect a group to align on the first try, especially if it’s about something that’s messy and complicated. Instead, get as much alignment as you can around something imperfect, move forward as much as you can, and revisit and revise based on your experience. The whole group will learn as it moves.

I use the “Squirm Test” and the “T-shirt Test” to help me gauge how aligned a group is. Simply put, if the group makes a decision, and someone starts to squirm, that person is not fully aligned. If people believe so strongly in a decision, they’re willing or even excited about wearing it on a T-shirt, they are aligned. Continue adjusting the stakes over time until the squirming goes away and everyone is wearing the T-shirt.

Create real-time feedback loops. Moving in alignment with others requires constant feedback. If you can’t see how your group is moving as a whole, you can’t adjust. The more real-time indicators you have (including the Squirm and T-shirt Tests) and the more transparently you work, the more likely others will be able to see and react to each other.

Remind each other what you’re doing and why. The best thing you can do when you’re struggling is to take a step back and remind yourself of why you’re going through this process. It’s helpful to remember times when you were in alignment with others and what it took to get there. It’s also helpful to remember times when you decided to take shortcuts without being fully aligned.

Moving in Alignment Is Hard

I’m particularly fond of physical (also referred to as “embodied” or “somatic”) practices as a way to viscerally remind yourself of what alignment looks and feels like and what it takes to get there. Pickup basketball is certainly one form of physical practice, but it’s not for everyone, and there are lots of other great practices that are a lot easier on the body.

One of my favorites is a group breathing exercise I learned from Eveline Shen, the Executive Director of Forward Together, a group that regularly uses a form of physical practice they call, “Courageous Practice,” as a way of staying grounded and aligned. It starts by standing in a circle and taking a few deep breaths together. You then add movement to your breath, raising your hand at a right angle as you inhale, and lowering it as you exhale. The goal is to breathe in alignment with each other. It helps to have a few people step out of the circle to act as observers, so that they can see how aligned the group actually is.

There are lots of different variations of this exercise. You can change the orientation of people in the circle, so that some people are facing inwards and other are facing outwards. You can stand in a line or some other shape. You can designate a leader or not.

It turns out that the simple act of breathing in alignment as a group is hard. Practicing not only helps you get better at it, but it also helps you develop strategies for moving in alignment that can apply to activities beyond breathing.

As difficult as it is to achieve perfect alignment, perhaps the most important lesson from this exercise is that, when everyone is trying, people are generally very good at breathing together. “Very good” is a worthy goal for any group trying to collaborate. As singular as that one pickup basketball game was for me, I’ve had many more experiences that were very good, and each of those were joyful, satisfying, and productive.

Alignment is a process. Set your expectations accordingly, and celebrate each victory along the way.

Many thanks to H. Jessica Kim and Kate Wing for reviewing earlier drafts of this post. Photo by Simon. CC BY-NC-ND 2.0.

Principles for Effecting Change in Complex Social Systems

Kano, Nigeria

In 2004, my colleague, Ruth Rominger, coauthored a wonderful piece in Reflections: The SoL Journal on Knowledge, Learning, and Change entitled, “Effecting Change in Complex Social Systems” with Hilary Bradbury, Sissel Waage, and David Sibbet. It cited five principles:

In creating social change, effective efforts…

Address immediate needs while linking them to larger, systemic issues. Successful change connects focused efforts with the web of political, economic, cultural, and environmental factors that frame and shape the immediate needs.

Surface discontents, build capacity, and elevate expectations. Successful change emerges from dissatisfaction with current conditions, but also celebrates many small victories as well as personal learning, thereby continually building momentum for innovation toward a preferred future.

Raise awareness of how social systems support and resist change. Successful change invites people working at multiple levels—individual, organizational, national, international, etc.— to experiment in creating new realities and transforming the forces that maintain the status quo.

Engage diverse people in partnering for positive action. Successful change is fueled by a mix of “un-usual” suspects—from those at the periphery of power to those closer to the center—in co-producing alternative futures in a context of mutual respect and relationships of trust.

Become the change, innovate with opportunitites, and persist. Successful change is grounded in personal transformation, encourages experimentation, and eventually evolves the system as a whole.

These words are still relevant, even ten years later.

Maximizing Collective Intelligence Means Giving Up Control

Ant City

Today marks the 45th anniversary of the Mother of All Demos, where technologies such as the mouse and hypertext were unveiled for the first time. I wanted to mark this occasion by writing about collective intelligence, which was the driving motivation of the mouse’s inventor (and my mentor), Doug Engelbart, who passed away this past July.

Doug was an avid churchgoer, but he didn’t go because he believed in God. He went because he loved the music.

He had no problem discussing his beliefs with anyone. He once told me a story about a conversation he had struck up with a man at church, who kept mentioning “God’s will.” Doug asked him, “Would you say — when it comes to intelligence — that God is to man as man is to ants?”

“At least,” the man responded.

“Do you think that ants are capable of understanding man’s will?”

“No.”

“Then what makes you think that you’re capable of understanding God’s will?”

While Doug is best known for what he invented — the mouse, hypertext, outlining, windowing interfaces, and so on — the underlying motivation for his work was to figure out how to augment collective intelligence. I’m pleased that this idea has become a central theme in today’s conversations about collaboration, community, collective impact, and tackling wicked problems.

However, I’m also troubled that many seem not to grasp the point that Doug made in his theological discussion. If a group is behaving collectively smarter than any individual, then it — by definition — is behaving in a way that is beyond any individual’s capability. If that’s the case, then traditional notions of command-and-control do not apply. The paradigm of really smart people thinking really hard, coming up with the “right” solution, then exerting control over other individuals in order to implement that solution is faulty.

Maximizing collective intelligence means giving up individual control. It also often means giving up on trying to understand why things work.

Ants are a great example of this. Anthills are a result of collective behavior, not the machination of some hyperintelligent ant.

In the early 1980s, a political scientist named Robert Axelrod organized a tournament, where he invited people to submit computer programs to play the Iterated Prisoner’s Dilemma, a twist on the classic game theory experiment, where the game is repeated over and over again by the same two prisoners.

In the original game, the prisoners will never see each other again, and so there is no cost to screwing over the other person. This changes in the Iterated Prisoner’s Dilemma, which means there’s now an incentive to cooperate. Axelrod was using the game as a way to try to understand the nature of cooperation more deeply.

As it turned out, one algorithm completely destroyed the competition at Axelrod’s tournament: Tit for Tat. Tit for Tat followed three basic rules:

  • Trust by default
  • The Golden Rule of reciprocity: Do unto others what they do unto you.
  • Forgive easily

Axelrod was intrigued by the simplicity of Tit for Tat and by how easily it had trounced its competition. He decided to organize a followup tournament, figuring that someone would figure out a way to improve on Tit for Tat. Even though everyone was gunning for the previous tournament’s winner, Tit for Tat again won handily. It was a clear example of how a set of simple rules could result in collectively intelligent behavior, highly resistant to the best individual efforts to understand and outsmart it.

There are lots of other great examples of this. Prediction markets consistently outperform punditry when it comes to forecasting everything from elections to finance. Nate Silver’s perfect forecasting of the 2012 presidential elections (not a prediction market, but similar in spirit) was the most recent example of this. Similarly, there have been several attempts to build a service that outperforms Wikipedia by “correcting” its flaws. All have invoked the approaches people took to try to beat Tit for Tat. All have failed.

The desires to understand and to control are fundamentally human. It’s not easy to rein those instincts in. Unfortunately, if we’re to figure out ways to maximize our collective intelligence, we must find that balance between doing what we do best and letting go. It’s very hard, but it’s necessary.

Remembering Doug today, I’m struck — as I often am — by how the solution to this dilemma may be found in his stories. While he was agnostic, he was still spiritual. Spirituality and faith are about believing in things we can’t know. Spirituality is a big part of what it means to be human. Maybe we need to embrace spirituality a little bit more in how we do our work.

Miss you, Doug.

Artwork by Amy Wu.