Case Study: Designing and Facilitating a Small Nonprofit Board Retreat with Zoe Tamaki


Over the past two years, I helped designed and facilitate two annual board retreats for a small nonprofit with my colleague, Zoe Tamaki. I don’t typically do one-offs like this, but the executive director was a friend of mine, and I was looking for an excuse to work with and learn from Zoe. After last year’s retreat, Zoe and I sat down in front of a camera and discussed some things we learned from the experience and from each other, including:

  • The importance of designing with your stakeholders
  • When relationship-building trumps task work
  • How I handled a funky facilitation moment

I’d like to share stories like this more frequently, and I hope to explore other mediums in which to do this, especially video. I want to share a lot more about design, which contributes much more to the success of group process than facilitation. I especially want to talk about the harder stuff — the challenging moments or the stuff that flat out fails. Since my focus over the past few years has shifted to supporting and coaching other collaboration practitioners such as Zoe, I’m especially excited to be sharing things I’m learning from them.

Finally, I hope to inspire other practitioners to share stories from their work more frequently and without concern about polish. This work is hard. It’s better to show all the rough edges.

Many thanks to Zoe for doing this work with me and for being willing to candidly debrief it on camera afterward! As I think you’ll be able to tell from the video, it was super fun working with her.

The Emperor Has No Clothes: Acting Strategically While Recovering from Process Trauma

A huge part of my job over the years has been helping groups recover from Process Trauma (and its ugly cousin Consultant Trauma). It’s caused when a group goes through some kind of process, such as strategic planning, and has a horrible experience. It almost always results in the group deciding never to pursue that process again unless they’re forced to, which exacerbates the trauma.

As empathetic as I am to Process Trauma, I am troubled that groups tend to give up on process rather than making adjustments and trying again. If I have a bad experience with a personal fitness trainer, I’m not going to give up on exercise as a path to getting healthier. Why do we do this with our work?

I think it’s because people often don’t understand why they’re going through a process in the first place. Instead of pressing for clarity, most folks accept it without questioning it. It’s the organizational version of the Emperor’s New Clothes. People assume that others must know better, or they’re intimidated by the terminology, and they give in.

Strategy work is rife with Process Trauma. However, strategy work matters because acting strategically matters. It’s the difference between systematically working toward your higher purpose and flailing in the weeds, trying to put out fires wherever you see them. It’s the difference between flowing in alignment with others and moving at cross-purposes. It’s the difference between success and failure.

I recently put together a short video where I explain what strategy is, how to develop good strategy, and how to build strong strategic muscles:

I hope this video helps people recover from Process Trauma while also clarifying why and how to do this work. I want to empower folks to speak up when the Emperor has no clothes. I want people to understand that skilled practitioners aren’t good at coming up with answers, but at helping the group ask and explore the right questions. I want people to understand that all good strategy is collective and emergent.

I also hope this video helps folks understand why tools like the Strategy / Culture Bicycle are designed the way they are and imagine alternative ways of using them. There’s no one right way to develop good strategy. It’s critical that groups approach it as something they need to figure out for themselves, which takes time and practice.

I would love to start a larger conversation about how to align around good strategy. Many strategy consultants are not intentional about helping groups align, which is why their processes often fail. However, collaboration practitioners who are intentional about alignment often stop there rather than making sure that what they align around is good. I touch on some of this in the video, but the devil is always in the details.

What strikes me about Hans Christian Andersen’s version of “The Emperor’s New Clothes” is that the emperor keeps walking, naked as the day he was born, head held high, even after the crowd starts hooting at him. Strategy is hard. If you’re not struggling at it, you’re probably not doing it right. But stubbornly marching ahead, ignoring the people around you, guarantees Process Trauma and failure. Good things happen when people know the purpose of a process, make adjustments when they struggle, and practice, practice, practice.

Thanks to H. Jessica Kim for reviewing an early draft of this post. Photo by Png Nexus, CC BY NC-ND 2.0.

Online Collaboration Isn’t Just About Meetings

COVID-19 has forced many of us to reckon with a working world where we can’t be face-to-face. I’ve been heartened to see how collaboration practitioners have been responding overall. I love seeing folks tapping the wisdom of their own groups before looking outward and sharing their knowledge freely and broadly.

I am especially happy to see people reminding others and themselves to pause and revisit their underlying goals rather than make hasty decisions. There is a lot of amazing digital technology out there, and it’s easy to dive head-first into these tools without considering other, technology-free interventions that might have an even greater impact in these difficult times. It’s been interesting, for example, to see so many people emphasize the importance of checkins and working agreements. When this is all over, I hope people realize that these techniques are relevant when we’re face-to-face as well.

After all, online collaboration is just collaboration. The same principles apply. It just takes practice to get them right in different contexts.

One adjustment I’d like to see more people make is to focus less on meetings. (This was a problem in our pre-COVID-19 world as well.) Meetings are indeed important, and understanding how to design and facilitate them effectively, whether face-to-face or online, is a craft that not enough people do well. However, meetings are just a tool, and a limited one at that. I’d like to offer two frameworks that help us think beyond meetings.

First, try not to think in terms of “online” or “virtual.” Instead, think in terms of work that happens at the same time (synchronous) or at different times (asynchronous), and collaboration that happens in the same or different places (remote).

Many collaboration practitioners tend to focus on synchronous collaboration — stuff that happens at the same time (which often ends up translating to meetings). I think some of the best opportunities for improving collaboration lie with asynchronous collaboration. Many of us assume that we can’t replicate the delightful experiences that are possible when people are in the same place at the same time. I think that’s narrow thinking.

Many years ago, I asked Ward Cunningham, the inventor of the wiki (the collaborative technology that powers Wikipedia), how he would describe the essence of a wiki. He responded, “It’s when I work on something, put it out into the world, walk away, and come back later, only to find that someone else has taken it and made it better.” To me, that beautifully describes what’s possible when asynchronous collaboration is working well, and it resonates with my own experiences. It also offers a North Star for what we’re trying to achieve when we’re designing for asynchronous collaboration.

Second, it’s important to remember that collaboration consists of three different kinds of work: task, relationship, and sensemaking. Breaking collaboration into these three categories can offer greater guidance into how to design and facilitate asynchronous work more effectively.

For example, a common type of task work for knowledge workers is creating documents. Agreeing on a single place for finding and editing documents hugely simplifies people’s abilities to collaborate asynchronously. It also better facilitates the kind of experience that Ward described than, say, emailing documents back-and-forth.

A common sensemaking exercise is the stand-up meeting, where everyone on a team announces what they’re working on and where they need help. (People are asked to stand up during these meetings to encourage people to keep their updates brief.) You could easily do a stand-up meeting online, but aggregating and re-sharing status updates over email is potentially more efficient and effective.

One interesting side effect of so many people meeting over video while sheltering in place is that we literally get a window into each other’s homes and even our families and pets, an emergent form of relationship-building. Pamela Hinds , who has long studied distributed work, calls this “contextual knowledge” and has often cited it as a key factor for successful remote, asynchronous collaboration. (It’s why, when we were designing the Delta Dialogues, a high-conflict project focused on water issues in the Sacramento Delta, we chose to rotate the meetings at people’s offices rather than at a neutral location. We wanted people to experience each other’s workplaces to enhance their sense of connection with each other.)

Once we recognize this form of relationship-building as useful, we can start to think about how to do it asynchronously. In my Colearning community of practice, which consists of ten collaboration practitioners across the U.S. and Canada, each of us posts a weekly personal checkin over Slack, often sharing photos and videos of our loved ones. We post and browse at our own convenience, and the ritual and the artifacts forge bonds that run deeper than what would be possible with, say, a monthly video call, which would be incredibly hard to schedule and would almost certainly prevent some of us from participating.

Similarly, we don’t need video to see each other’s faces. A trick I stole from Marcia Conner many years ago — well before video was ubiquitous — was to get silly photos of everyone on the team, combine them in a document, and have everybody print and post it on their office wall. This not only enhanced our conversations when we were talking over the phone, it created a constant sense of connection and fun even when we weren’t in a room together.

While I hope these examples dispel the notion that synchronous collaboration is inherently more delightful and impactful than asynchronous, I also want to acknowledge that designing for asynchronous collaboration is more challenging. I think there are two reasons for this.

First, you have to compensate for lack of attention. When everyone is in a room together, it’s easier to get and keep people’s attention. When people are on their own, you have no control over their environment. You have to leverage other tools and techniques for success, and you’re unlikely to get 100 percent follow-through.

The two most common tools for compensating for lack of attention are the artifact and the ritual. An artifact is something tangible, something that you can examine on your own time, whether it’s a written document, a picture, or Proust’s Madeleine. A ritual is an action — often with some cultural significance — that’s repeated. It could be a rule (with enforcement) or a norm that people just do. It’s effective, because it becomes habitual, which means people are able to do it without thought.

The trick is finding the right balance of artifacts and rituals. At Amazon, Jeff Bezos famously requires people to write a six-page memo before meetings, but they designate shared time at the beginning of each meeting to read the memo together. On the one hand, writing the memo requires discipline and attention in-between meetings, or asynchronously. On the other hand, rather than save meeting time by having people read the memos beforehand, they devote synchronous time to reading the memos together. I can guess the reasons for this, but the truth is that I don’t know what they are. Different practices work in different contexts. Everybody has to figure out what works for themselves. Certain kinds of cultures — especially transparent, iterative, developmental ones — will be more conducive to these kinds of practices.

Finally, our relationship to technology matters, but maybe not in the way you think. On the one hand, if you are going to use a tool for collaboration, then it’s important to learn how to use it fluently and wield it skillfully. On the other hand, technology has this way of making you forget what you already know. It may be that the tools that will be most helpful for you have nothing to do with the latest and greatest digital technology.

This has always been easy for me to understand, because I have always had an uncomplicated relationship with technology. I love technology, but its role is to serve me, not the other way around. When I design structures and processes for collaboration, I always start with people, not tools, and I try to help others do the same.

What I’ve come to realize over the years is that this is often hard for others, because they’re worried about what they don’t know and they have a block when it comes to learning about technology. I get this. I have blocks about learning many things, and I know that advice that amounts to “get over it” is not helpful. Please recognize that these feelings are not only real, they’re okay. While I’d encourage everyone to find peers and resources that help them learn about digital tools in a way that feels safe, I also want to remind you that collaboration is ultimately about people. Keeping your humanity front and center will not only help you with your transitions to remote work, it will help you through this crisis.

The “Secret” to High-Performance Collaboration Is Practice

On March 22, 2017, I had the pleasure of giving the keynote at The Collaboratory 5, a forum of about 200 Jewish innovators and entrepreneurs focused on grassroots change. My talk was on my favorite topic and the driving force behind my work for the past four years: how practice can lead to better collaboration.

Afterward, I led the whole group through the one-minute drill, followed by two breakout sessions where I led smaller groups through a power workout (including power video analysis and playing with status). My goal was not only to tell people how important practice was, but to lead them through an experience where they could get a sense of what I meant by practice and its value, especially if repeated over and over again.

I had an incredible time. It reminded me how different this mindset around practice is and how much I enjoy talking about and doing this stuff with new audiences. I’m looking forward to giving more talks and workouts in the near future. (If you’d like me to do this with your group, drop me an email.) Many thanks to my friend and colleague, Adene Sacks, for referring me and to Lisa Lepson, Jenny Kibrit Smith, and all of the organizers for inviting me and for being great hosts! Thanks to Duane Stork for the photo above.

Here’s a video of my talk!

Edited Transcript

Here are my slides and a tightly edited transcript.

What’s the best collaborative experience you’ve ever had? It could be personal or professional, with one other person or a large group, etc.

How many of you were able to come up with an example?

How many of you came up with one easily?

The story I want to share today has nothing to do with my work and didn’t even involve me. I have a friend who used to teach violin. She would start her beginning students by teaching them variations of Twinkle, Twinkle, Little Star. The first time I saw her teach, she was teaching this very serious five-year old. Toward the end of the lesson, after numerous repetitions, my friend — who was playing alongside her student — decided to harmonize the last few bars. When she heard the harmony, the little girl’s face just absolutely lit up.

I’m lucky to have been a part of and to have seen and studied many great collaborative experiences. But that time I watched that little girl’s face light up upon experiencing that simple little harmony that she herself was a part of stands out in my mind. I get chills thinking about that moment, because hearing that simple little harmony lit me up too.

When I ask folks about their best experiences collaborating, most people have a hard time coming up with an example. But, whether you can easily recall an experience or not, I think everyone has had a moment like that little girl had with Twinkle, Twinkle, Little Star. We all have an intuition about what great collaboration should feel like, even if we have low expectations about getting to experience it.

What would your world be like if all of your experiences collaborating were at least as good as your best?

What would the world be like if everybody’s experiences collaborating were at least as good as their best? Imagine this world for a moment, and soak in the feeling.

Practice

My mission for the past 15 years has been to create a world where everyone’s baseline experience with collaboration feels exactly like that little girl did when my friend started harmonizing with her.

How do you do this? How do you help improve everybody’s collaborative experiences?

Said another way, what’s the secret to high-performance collaboration, and how do you scale this?

About five years ago, I realized that most of my successes in helping others collaborate more effectively were hollow. We would do good work together side-by-side, we would achieve good outcomes, and people would have a good experience getting there. But when I left, most groups would fall back on old habits. I was like a ringer in basketball. If I played on your team, I could help make everyone better, but once I left, the team would revert back to what it was. Maybe folks picked up a thing or two along the way, but the impact wouldn’t be what I wanted it to be.

So I decided to rethink how I did the work. To help me do this, I started with the premise that collaboration is very hard to do well. If it weren’t, we’d all be doing it already, and it would be simple for everyone to come up with examples of great collaboration.

Then I thought about what it takes to achieve things that are very hard. I thought about things like playing the violin or learning a language (my personal bane). And my conclusion was simple.

The more you practice, the better you will get at collaboration.

Things that are hard require lots and lots of practice to do well. Everyone is capable of doing them better. You either put in the time, or you don’t. And if you don’t, you generally aren’t going to be successful.

Simple, right? Maybe so, but to me, this was a revelation. I realized that everybody I ever knew or saw — myself included —who was good at collaboration had had lots of opportunities to practice, whether it was conscious or not.

How much practice do we need to get really good at collaboration?

Consider one example of high-performance collaboration: professional basketball.

Professional basketball players play six months out of the year — November through April, not including the playoffs. They play 82 48-minute games over the course of their season — about 66 hours total, or 11 hours a month.

11 hours a month! Great job, right? Of course, they’re working a lot more than 11 hours a month. The rest of the regular season — about 93 percent of their actual working time — they’re practicing, training, working on fundamentals, both individually and as a team.

We’re talking well over a 9:1 ratio of practice to performance. Performance, of course, is a form of practice, but the main distinction I’m drawing here is that, when you’re performing, the results count. You can afford to fail a lot when you practice — that’s all part of the process.

Think about your job for a moment. How much of your job relies on collaborating effectively with others? What percentage of your time do you spend practicing versus performing?

I’m not arguing that 9:1 is the right ratio in every context. But I’m going to guess that, for most of you, your ratio is pretty much the opposite of this, and I think that a 1:9 ratio is definitely wrong. Folks who care about getting better rarely consciously consider how they can practice more.

Our predominant culture believes that collaboration is some special knowledge that, once acquired, will magically make groups better. All of our learning mechanisms are oriented this way. We scour articles looking for magical tricks, we invest in magical apps, or we hire consultants whom we hope will share some magical secret.

At the end of the day, none of that works very well. If we want to get better at collaboration, we need to find ways to incorporate a lot more practice, to get our practice-to-performance ratios up.

How do we do this?

Supporting Practice

One way is to provide more structures for encouraging practice. To explain what I mean, consider fitness.

Fitness already has a culture centered around practice. We don’t technically need any structures to help us do that, but structures help. To understand how, let’s map out the ecosystem of structures that support practice in physical fitness along two axes: supply (how much of it is available) and cost.

We’ve got lots of books and free articles on the Internet that give us advice. Those go in the upper left of our chart.

You could work out with a friend or enroll in a gym or take a class or a bootcamp. Some of these things are free, and some cost money, but they’re all still relatively cheap, and there are quite a few options.

You could also hire a personal trainer. These are the most expensive options, and they’re the least used of the options, so we’ll put them on the lower right.

I’m going to claim that this is an ecosystem that more or less works. If we want to get fit, we can find all sorts of structures across a broad price spectrum that will support us in doing so.

What does the collaboration ecosystem look like?

As with fitness, you can easily find thousands of pretty decent articles that explain how to get better at collaboration.

There are plenty of one-off trainings, some of which might even be pretty good.

You could go to business school. This is more on the high-end in terms of cost.

And there are a plethora of folks like me — the equivalent of a personal trainer — you could hire.

This ecosystem favors the high-end. We have very few structures in the middle, which means that there are a lot of people who get left behind.

I would argue that, if we want to support more collaboration practice, we need the collaboration ecosystem to look more like the fitness ecosystem.

We don’t need as many options in the high-end, and we need something to fill in the middle. If we could figure out how to shift the collaboration ecosystem so that it looks more like this, then I think more people would be practicing collaboration. If more people practiced collaboration, a lot more groups would be good at it, and we’d start getting closer to this vision of a world where everybody’s baseline experience with collaboration is a great one.

Muscles

How do we shift the collaboration ecosystem so that we’re doing a better job of encouraging and supporting effective practice?

First, we have to get clear about what we’re talking about when we’re talking about “collaboration.” We need to get more concrete about what we mean by “collaboration muscles.”

Collaboration is an aggregation of several skills, some of which are context-dependent. For example, good communication — listening in particular — is clearly important. Your ability to recognize and navigate power dynamics in groups is also important.

Over the past four years, I’ve identified and refined a set of muscles in four different muscle groups.

Once we’ve identified specific muscles, the exercises (or workouts) start to become clearer. I’ve aggregated a bunch that I use on my website, which I’ve made public domain so that you can do whatever you want with them. I’m not going to say too much more about these now, as we’ll do a listening workout together after I’m done talking, and I’ll be leading power workouts in both the morning and afternoon breakouts.

What’s important to remember about these exercises in the context of practice is that doing them once or a few times or even ten times isn’t enough to be useful. You have to repeat them over and over and over again to develop your muscles, and you have to be intentional about how you practice.

Finally, once we know what the workouts are, we can start developing programs to support them — the equivalent of gyms or bootcamps, the equivalent of exercise “equipment” or apps, muscle assessments, etc. And voila, the ecosystem will start to shift the way we want it to shift.

Shifting Culture

At the end of the day, what I really hope to achieve is a shift in culture. I simply want people to associate improving at collaboration with lots and lots of practice. I hope that all of you walk away from this talk thinking about how you can integrate practice more in your own work and lives, and I hope you’ll try to convince others to do this as well.

If enough of us start doing this, culture shift will happen. Still, I don’t want to make light of how difficult this shift I’m describing will be, both societally and also individually.

Over the past four years, I’ve completely changed how I work with groups. Instead of being a ringer on a basketball team, I’m now their workout instructor. It’s been successful enough that I continue to do this work this way, refining the process along the way. My biggest takeaway, however, has not been how valuable practice is, but how emotionally challenging the journey can be.

To close, I want to share a personal story about what it takes to learn something hard through lots and lots of practice.

One of the things that I am really bad at is learning languages. I don’t speak Korean, which has always been a sore spot for me, as it’s prevented me communicating with many of my relatives and even my own parents, to some extent.

About five years ago, my mom invited me to go to Korea with her. In preparation for this trip with my mom, I decided to enroll in my very first Korean class. I knew that it would take a lot of practice to learn, and I used every trick in the book to try to support me in this. I had lots of people supporting me, and I was super motivated. But I wasn’t having much success, and it was killing me.

At some point, it hit me. Babies are really good at learning languages, and my sister recently had a baby! My nephew, Benjamin, is six now, but he was about one when I was about to go on this trip, so we were both learning a new language at the same time. I decided to watch him closely to see what tips I could pick up from him.

Here’s what I learned. Benjamin, my one-year old nephew, really sucked at speaking English. He was really, really bad. But what was different was that he didn’t expect to be good. When he did speak, everybody — including me — would go nuts! It didn’t matter if what he said made any sense or if he pronounced the words correctly. We would all laugh and coo and celebrate, and he would clearly respond to that. Learning a language, for my one-year old nephew, was a joyful experience, not a painful one.

This was a revelation to me. Benjamin took a good three or four years before he spoke English more or less fluently and correctly, and it was a joyful experience all the way. Here I was, beating myself up after a few weeks of Korean classes, where I wasn’t even fully immersed, thinking for some reason that I needed to be speaking Korean better than I was. What if I assumed that I was going to suck for a long time, and instead of beating myself up for it, celebrated the same way we celebrated Benjamin?

Getting good at collaboration is really hard. It takes practice to get good at it. If we’re really going to get good at it, we all have to learn from Benjamin’s example. We have to understand that we’re going to trip and fall and suck for probably a long time, but we can still celebrate the little victories along the way. And if we give ourselves enough time, we will eventually get so good at it that we won’t even think about it.

Imagine that. What would our world look like if we all became that fluent at collaboration?

Thank you very much!