colearning – Faster Than 20

End-of-Year Journey Mapping: How my 2020 Went and How 2021 Is Looking

Four years ago, I started organizing a small end-of-year gathering with other Bay Area collaboration practitioners to celebrate and make meaning of the year together. We would spend the first few hours of our session mapping how our individual years went using an exercise called Journey Mapping, then we would share our respective stories with each other and toast the end of the year with libations and snacks. It was a lovely ritual, and it became an annual tradition.

This past year, we couldn’t do a face-to-face gathering due to the pandemic, so we decided to do it remotely instead. Going remote had three wonderful benefits. We were able to divide it into two sessions, which netted us more time. We were able to invite more people, including folks who lived outside of the Bay Area. And, it was a good kick-in-the-pants for me to write up the exercise so that others could organize their own gatherings. (Several folks did, which made me incredibly happy.)

Journey Mapping is a quick way of visually telling the story of a project’s highs and lows over a bounded timeline. (Product managers may be familiar with customer journey mapping, which is similar in spirit, but different in practice.) You can do the exercise on your own, but it’s nicer in a group setting, even when everyone is doing it for themselves (as we do in our end-of-year ritual). It’s like working out with a buddy — you’re more likely to do it if others are doing it with you, and it’s a wonderful way to support each other and build community. When you do it as a group on a shared project, it serves as a fantastic tool for making meaning together and for discussing and developing shared narratives. I often use it as a ritual for teams to celebrate, mourn, learn, and transition.

How you do the exercise is not as important as simply making time to reflect regularly. The more you do it, the more you’ll understand how best to adjust it for your specific situation. That said, Journey Mapping has three attributes that I think are particularly powerful.

First, it contextualizes your work in your overall life. The toolkit specifically asks you to map highs and lows both professionally (or with a specific project) and personally. In a team setting, the tendency is to skip the personal brainstorming, especially when you have limited time. Sometimes, this is warranted. However, you lose a lot when you do this. Several years ago, I did this exercise with a startup’s leadership team, which was struggling mightily with interpersonal dynamics. Earlier that year, they had been running out of money, and they weren’t sure they would be able to raise another round of investments. Not surprisingly, that was a low point professionally for everyone. At the same time, one of the leaders had also been dealing with a family tragedy and the dissolution of a relationship. The rest of the team never knew about this and only found out about this through the Journey Mapping exercise. Learning about their teammate’s personal struggles many months after the fact caused them to re-examine how they viewed their behavior during that time, leading to greater empathy, a little regret, and ultimately forgiveness.

Second, the Journey Mapping exercise asks you to list the highs and lows from memory first, then to review your calendar, journal, and other artifacts and add anything you might have forgotten. This reminds you that what you might be feeling and remembering in the moment is rarely the whole story and that there may be lessons to harvest or things to celebrate that are worth revisiting. It also reminds us of the importance of having and reviewing artifacts.

Third, the Journey Mapping exercise encourages you to take your somewhat structured set of sticky notes and create meaningful art out of it. For example, these were the sticky notes that I created for my 2020 (using Sticky Studio):

and this was my artistic rendition:

This part of the exercise almost always gets short shrift. We often treat art as optional — nice, but not necessary. Doing this end-of-year ritual with my colleagues the past four years has helped me realize that this is a mistake, not just with Journey Mapping, but with many of my exercises. Practically speaking, when you create something that’s beautiful, you’re more likely to look at it again. More importantly, the act of creation leads to an understanding that’s far deeper and more meaningful than a set of sticky notes can convey.

You can get a taste of what I mean by looking at the art that some of my colleagues created:

Everybody chose to tell their story differently, from emphasizing specific themes (e.g. needing space, “re-“ words) to capturing a larger metaphor (e.g. tree, river). My colleague, Catherine Madden, organized her year into five categories and wove her story into the tapestry on the right — you can read more about her story and process here. Seeing what people created and listening to their stories were incredibly moving. I will remember those stories in a way that I don’t think would have been possible if they had simply told them or shared their sticky notes. Moreover, I don’t know that they would have told the stories the way they did if they had not had the chance to create this art.

My 2020

The personal backdrop for my 2020 was — like everyone’s — all about the pandemic. I was incredibly fortunate to be healthy and safe and not to lose anyone to COVID-19. So many people were not that lucky. The numbers are staggering — 2.2 million deaths worldwide so far, 450,000 in the U.S alone. (For comparison, 400,000 Americans died in World War II.) What made it all the more heartbreaking — especially for someone whose purpose is to help society collaborate more effectively — was how divided and misaligned we were in these trying times.

I was way luckier than most, but pandemic life was still hard. I spent the spring simply trying to cope. Like many people, one mechanism I tried was growing plants. I found a wilted mint sprig in the back of my refrigerator, which I rooted in water for several weeks, then transferred to a pot. I observed and documented the process every day, occasionally sharing what I saw on Instagram. My partner, amused by the loving care I was showing my plant, named it, “Mo.” I was awed by how resilient my mint was, and I was also surprised how gratifying this simple, regular practice of paying attention to Mo Mint felt.

Resilience. Paying attention. These became recurring themes both personally and professionally. I went into 2020 hoping that I could spend 30 percent of my time on coaching and training individual collaboration practitioners. I felt that this would be the best path to maximizing my impact, and it’s also where I felt the most energy and joy. A third of the way into the year, as the lockdowns were starting, it was clear that I wasn’t getting enough traction to hit that number.

I also went into 2020 adamant that I would only take on organizational clients willing to try my muscle-building approach to addressing their challenges. Convincing clients to do this has always been difficult, but my yield in the first half of 2020 was even lower than what it usually was. In an interesting twist, both the pandemic and the racial unrest created demand around collaboration practitioners who could help with remote work and equity work. However, most of the prospects who came my way were more interested in quick fixes than the kind of deep work that real change requires.

Grappling with those two things in concert was hard enough. Doing so during a pandemic was even harder. Paying attention and focusing on resilience made all the difference in the world.

The previous year, I had started to experiment with video as a way to better communicate my frameworks and practices, and I had more ideas and partially written scripts than time to produce them. Several conversations I had been having with colleagues inspired me to revisit one of these videos, Acting Strategically, which I published in April.

The response was universally positive, with many people asking me, “What would it look like for me or my organization to do this?” This led me to dust off some workouts I had developed over the years and start piloting them with colleagues and friends. The pilots performed well, and I loved doing them. I started preparing an “official” offering for late 2020, when something unexpected happened. Focusing on strategy was helping prospective organizational clients understand my workout approach in a way that had failed to click otherwise. Even when it was clear that they needed to focus on areas other than strategy, because they were better primed for this approach, they were more open to using workouts to address other aspects of collaboration.

By late summer, I found myself doing workouts with several organizational clients. It was gratifying and generative, but it was also taking my energy away from my individual practitioner offerings. I was conflicted, but I ultimately decided to go with where the demand was taking me and to hold off on my individual offerings indefinitely.

Looking Forward and Backward and Forward Again

Doing the Journey Mapping this past December had one more interesting twist. A few years earlier, Catherine Madden had suggested doing the exercise as a way of looking forward, not just looking back. At the beginning of 2020, I decided to try her suggestion, drawing what I imagined my professional curve might look like at the end of 2020. Here’s what I drew:

It was fascinating to compare this with how my year actually went. I had imagined a choppy beginning with a gradual upward trend, and I wasn’t completely wrong. However, the choppiness ended up being twice as long with an overall downward trajectory, there was never any “big” win, and while my year did end on an higher note, it wasn’t as high as I had hoped.

Still, as with all scenario work, the goal wasn’t prediction, it was to prepare for possibilities. Because I had imagined that my year would be choppy initially, I was mentally and emotionally prepared when that turned out to be true. I had also adjusted my strategic goals accordingly, so even though they ended up being off, they were not as off as they probably would have been otherwise. Finally, because I had written it all down, I had something to look at and reflect on at the end of the year.

I am determined to do this exercise again for 2021, but it’s already February. I’m about two months behind where I usually am in terms of planning, and I find myself more unmoored than I’ve been since starting this Faster Than 20 experiment seven years ago. I’m trying to be compassionate with myself. Last year was not normal, and while there are some positive signs, we’re not out of the woods yet, and there’s still a lot of uncertainty moving forward. I’m still excited about providing workouts, coaching, and community for collaboration practitioners. I have a set of clients I’m currently supporting, I have some ideas of what I want to offer individual practitioners later this year, and I will undoubtedly continue to experiment. Beyond that, I just don’t know.

What I do know is that rituals, community, and time to reflect matter. I am always grateful for my peers and our end-of-year gathering, but I feel especially so now. I hope many of you find Journey Mapping valuable as well.

Podcast: Play in new window | Download

Subscribe: RSS

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.

Podcast: Play in new window | Download

Subscribe: RSS

What We Learned from Five Years of Check-ins

The two of us have never worked with each other.¹ We share some values, interests, and colleagues, but we are in marginally related fields. Kate’s into fish and data, whereas Eugene is obsessed with all things collaboration.

Yet for the past five years, we have been taking an hour almost every week to check in with each other. It’s been one of our most valuable practices as independent practitioners, and we think you might find it valuable as well. Here’s how these check-ins came about, how and why we do them, and how you could do them too.

How We Got Here

We first met in April 2011 at a meeting about building networks for social change. Eugene wanted to make a point about the importance of reciprocity, and for some strange reason he brought a bunch of green pipe cleaners to help him do it. Stranger still, Kate got it immediately, fashioning one of them into a shark and remora and giving it to Eugene.²

In the ensuing three years, we mostly followed each other on Twitter, occasionally sharing a link or a snarky comment. Then, in 2013, Eugene decided to leave the consulting company he had co-founded, and a year later, Kate decided to leave her foundation job and take a semi-sabbatical. Kate reached out to Eugene to ask about his experience consulting. A few weeks later, Eugene invited Kate to be weekly check-in partners as part of a larger experiment in “colearning.” Kate wasn’t entirely sure what this meant but as she was trying to learn new skills, she decided to give it a chance.

On Monday, June 13, 2014, we had our first call. Five years and 170 pages of notes later, we’re still checking in weekly. We often lean on each other for advice, and we’ve both relied on each other to get through some tough times. Our real-life partners half-jokingly refer to us as work husband and wife.

What Is a Check-In?

Our check-ins are loosely structured. We maintain a standing time when we can. We talk for an hour, often a little longer. We usually talk by phone or video chat, but sometimes face-to-face, especially if there’s food.³ We talk about what we’re working on and what we’re thinking about, as well as what’s going on in our lives. We take shared notes while the other person talks, which helps us listen and see the patterns in our thinking. We laugh a lot, and we’ve cried some as well. Sometimes, we wrestle with a complicated problem or test ideas. Sometimes we go on silly riffs that eventually result in fruitful ideas.

We generally split the time — one of us starts talking about the week that’s passed and then hands off to the other — but we don’t time each other. Sometimes, one person needs more time than the other. We usually pick up on this quickly and give each other that time. This works beautifully, but we’re both self-conscious about taking up too much space, so we often stop and ask if they need a turn to speak.

There’s one thing we always do at the end of every check-in: We share a beautiful thing we saw or experienced. It can be surprisingly hard to remember a beautiful thing that happened during the week, especially if you’re having a bad day. Knowing that we are expecting each other to share something makes us both pay more attention to things that we think are beautiful.

What Are We Getting out of This? Why Are We Still Doing This?

We originally started check-ins because we wanted the collegiality, learning, and heightened performance you get from being in a good company without having to actually be in a company.⁴ As an independent operator, you may work with a team for the scope of a single project, but you have a specific task and then you move on. You don’t have regular contact with the same group over months or years, which can allow you to grow and improve from the group’s feedback over time. Checking in weekly was an important part of Eugene’s experiment, even though at first it seemed like a lot of time.

We quickly learned that frequency led to efficiency and depth. We didn’t have to spend the first 20 minutes of each conversation “catching up” and getting up to speed because we were already caught up. That meant we could dive into deeper issues faster. Our weekly allocated check-in time feels luxurious. It’s one hour where we get to say whatever is on our minds and we get to be heard.

Regularity and transparency also support accountability. We both had things we wanted to get done, and we knew the other person knew this, so when our next check-in rolled around, we got them done or tried to explain why we couldn’t. Soon, we started asking each other more explicitly to hold each other accountable, especially for the stuff we badly wanted to do, but often found ourselves delaying.⁵

One time, Eugene kept postponing a task until finally, he gave Kate $20 and said she could keep the money if he didn’t finish his task by the next check-in. He finished the task and got his money back… barely.⁶ Doing it together and making it silly helped, but talking through why he kept postponing the task helped even more.

Make your own Check-Ins

Why have our check-ins worked so well? It’s equal parts chemistry, timing, and practice. We like and respect each other a lot, we’re both reasonably self-aware and reflective, and we’re both constantly trying to get better. We’re both in the middle of our careers, so we’ve seen some things and have some skills, but we’re also still learning. We’re both supportive, but we’re also not afraid to speak our minds, and we’ve both given each other some tough love in the past.

Still, we don’t think we are outliers. We think that everyone would benefit from something like this. We’d encourage you to try it for a finite amount of time, then adapt. Specifically:

Don’t give up just because it didn’t work the first time. Experiment with format. Experiment with partners. There are lots of ways to structure a check-in. Try a few, and keep what works.
Talk about how you’re going to talk, not just what you’re going to talk about. We both tend to think out loud, where talking through a thing helps us better understand it. That means we tend to let the other person run on for a while before interrupting or asking questions. You might prefer to interview each other. Don’t be afraid to say, “This is the part where I just need you to listen and not try to solve the problem.”
It’s not therapy. It might feel therapeutic — helping you examine where you’re stuck on a work thing or what you need to focus on — but we’re not asking you or each other to dig deep into your psyche or your childhood. Find a trained professional for the really hard stuff.

The beauty of regularly showing up and listening to another person is that it’s practice for all aspects of our work and life. It’s practice in helping others grow and evolve. It’s practice in giving yourself the space to be whom you want to be. We’ve benefited so much from this practice, and we think others would as well.

Eugene Eric Kim helps groups learn how to come alive and collaborate more skillfully together. He spent ten years consulting with companies across different sectors, from Fortune 500 companies to grassroots movements. He’s now focusing his efforts on helping others develop the same skills that he uses to help groups.

Kate Wing is a design strategist who works with clients to improve their impact, and has a particular fondness for all things fish. She founded the databranch to build better data and technology systems for conservation and she has a wide breadth of experience in the social sector, from philanthropy to government.

This is the fourth in a series of blog posts about building a network of collaboration practitioners. The others are:

Building a Network of Collaboration Practitioners (February 7, 2019)
A Personal Case Study in Network-Building: Pre-IPO (February 20, 2019)
A Personal Case Study in Network-Building: Selfishness, Frequent Collisions, and my Colearning Experiment (May 7, 2019)
What We Learned from Five Years of Check-ins (May 14, 2019)
Design Sketch for a Network of Collaboration Practitioners (November 14, 2019)

A Personal Case Study on Network-Building: Selfishness, Frequent Collisions, and my Colearning Experiment

In 2013, I left the consultancy I had co-founded to rest, reflect, and reconsider my approach to helping groups collaborate more effectively. That time led me to the premise that has become the foundation of my work since — that getting better at collaboration is “simply” a matter of practicing, and the more we figure out how to encourage practice, the better we all will get at collaboration.

I wanted to explore this premise while also taking care of myself and maintaining balance in my life. I was not ready to start another company, but I was also afraid of feeling isolated. I had felt that way for much of the early part of my career, and being part of a tight-knit team at my consultancy had been a huge joy. I wanted the best of both worlds — the support, learning, and joy of being part of a close team along with the freedom and flexibility of being independent.

I think many people’s first instinct for addressing professional isolation, especially as an independent, is to form a group that meets once a month or a few times a year. I think this is a great thing to do, and I think more people would be well-served if they did this. However, I wanted deeper relationships and learning than an occasional coffee with colleagues would provide.

First instincts also don’t always result in optimal designs. I wanted to model a less knee-jerk, more decentralized approach to creating communities of learning and practice. Specifically, I wanted to play with two design principles:

Be selfish, but in a networked way
Frequent collisions

Armed with this clarity, I started to experiment.

Be Selfish, but in a Networked Way

When it comes to teams and networks, I often hear rhetoric around the importance of “selflessness.” I understand and appreciate where this comes from, but I don’t think that this is the best framing. Groups perform best when individual interests align with those of the group. You want people to find that alignment without sacrificing their individuality. Because many good collaboration practitioners tend toward the self-sacrificial, I often find myself encouraging others to “be selfish.”

As I embarked on building a new network for myself, I wanted to model selfishness (in a networked way), trusting that my self-interest strongly aligned with a larger, collective purpose. “In a networked way” meant finding ways to share and to encourage emergence without interfering with my selfish goals.

Here’s an example of how this manifested. In late 2014, a colleague had introduced me to Janne Flisrand, a Minnesota-based practitioner who was doing interesting work. Janne was planning on visiting San Francisco and asked if I wanted to grab coffee while she was there. I said yes, then, on a whim, asked:

If I organized a meetup for you, would you be willing to chat informally about your work? I’m sure I could pull together at least 3-5 good folks, and we could continue the conversation over dinner as well.

Here was my selfish reasoning:

I valued the opportunity to have some get-to-know-you time, but I also wanted to dive more deeply into Janne’s work. Coffee sessions aren’t usually long enough for that.
If I found value in a deep dive, I figured others would find value in it as well. It wouldn’t hurt me to invite a few others. Worst case, everyone would say no, and I’d get lots of one-on-one time with Janne, which was the original plan anyway. Best case, other good folks would come, other relationships would get built, and awesome stuff would emerge from that.

Janne was enthusiastic about my offer, which meant I was now on the hook for trying to organize something. Once again, I wanted to experiment with this principle of maximum selfishness (but in a networked way). This was how it played out:

Scheduling. Rather than see who was interested in attending, then trying to find a date that worked for everyone, I picked a date that worked for Janne and me, then invited others to accommodate our schedule. No mass Doodles!
Venue. I invited people without picking a specific location, then asked if someone would be willing to host. I figured that if no one responded, then I was no worse off than I was before. However, if someone did respond, then I wouldn’t have to find a space at all, which appealed to my selfish (and lazy) side. As it turned out, someone did end up offering to host!
Invitations. I only gave people one week’s notice. If shorter notice meant less people, then we would simply have a more intimate conversation and I wouldn’t have to find as big of a space. If we got lots of people, then my community would start to become more interconnected, which makes me happy and often results in something interesting. Either way, it was a win. I didn’t think too hard about whom to invite, and I ended up asking 18 people. To my surprise, 12 said yes, and some folks asked to bring guests!
Design. I wanted to model something that was participatory, but also easily replicable. That meant not investing a lot of time designing anything too intricate. I decided to do a simple fishbowl, where Janne and I would sit inside a circle with two other empty seats, and others could join the conversation simply by grabbing one of the empty seats. Afterward, we’d invite whomever wanted to join for drinks and dinner.

It took me less than an hour to:

Conceive of this experiment
Think of some additional folks to invite
Invite them

This small investment in time enabled me to convert a coffee date into a wonderful gathering, where I got to delve further into a colleague’s work with a dozen great colleagues and to introduce these folks to each other, all without having to juggle calendars or find a space! As always happens, interesting stuff emerged from this gathering, including one new relationship resulting in a large new project for a colleague.

This experiment worked so well, I decided to continue it over the next two years, playing with different variables, but always strictly conforming to this principle of networked selfishness. I tried to manage expectations by being transparent about my organizing principles and by constantly encouraging others to be similarly selfish. My hope was that selfish replication would result in lots of self-organizing and interconnection among Bay Area practitioners. This didn’t happen as much as I would have liked, but I was happy about the good things that did emerge from my small acts of networked selfishness.

Frequent Collisions

Another design principle I wanted to explore was frequent collisions. Many years earlier, I had read a wonderful article about how people with sisters tend to be happier. It postulated that this was because people tended to speak more often with their sisters than their brothers. As someone with two sisters, this resonated.

It also jived with my experiences on teams. At my company (which was virtual), I talked to my co-founder every day, I talked to my other teammates several times a week, and we used online tools to stay in touch asynchronously. We talked a lot about work, but we also talked about our lives, and often, we were just silly. Because we talked frequently, we didn’t have to spend a lot of time catching each other up on things, and it was easy to dive right in and also to give each other support.

This was in the back of my mind when I got an email in 2013 from my friend and colleague in Montreal, Seb Paquet, suggesting we catch up. Our resulting conversation reminded us both how much we enjoyed talking with and learning from each other. Rather than wait around for another excuse to schedule a catch-up, I proposed that we schedule a weekly standing time for the next four weeks with no agenda. To my surprise, Seb accepted.

We called the experiment, SEEK, a somewhat garbled, but easy-to-pronounce combination of our initials. We talked a lot about both our work and our lives. Because we were talking regularly, we didn’t have to provide context and background each time we spoke, which allowed us to get deep quickly and consistently.

At the end of each conversation, we recorded a three-minute video where we each shared one takeaway from the conversation. It was a way to have a private, intimate conversation while also leaving a public trail, hopefully provoking conversations with other colleagues while also inspiring others to replicate our experiment.

Seb is incredibly smart and thoughtful, and talking with him enabled me to crystallize and sharpen what I was learning from many of my experiments. For example, here’s the video takeaway from our second conversation, which not only led to some significant changes to my Goals + Success Spectrum, but was also the impetus for me to package and share what has become my most popular and impactful toolkit:

Despite being incredibly busy, we both found our regular conversations productive and gratifying. Each week, we both found ourselves looking forward to our next session. After our four-week experiment ended, we decided to continue talking weekly. We ended up more or less maintaining our weekly pace for three more months.

Colearning Experiment

My experiments with Seb helped validate my desire for frequent engagement. It also helped validate my “selfish” approach. By asking for what I really wanted — in this case, frequent engagement — I not only got what I wanted, but so did my partner. I was ready to ask for even more.

In late 2013, I pitched an idea to five colleagues. They were all Bay Area-based independents, all changemakers, all collaboration practitioners at some level. I knew all of them well, and they knew each other somewhat, mostly through me. I asked them to engage in an eight-week experiment where we would all pair up and commit to checking in with our partners once a week for eight weeks. After each checkin, we would all share one takeaway on a shared mailing list.

Four of my colleagues — Pete Forsyth, Rebecca Petzel, Amy Wu, and Odin Zackman — agreed! Acknowledging a problem that we all shared, Odin cheekily suggested that we call ourselves “COBI” for “Chronically Overwhelmed, But Improving.” We eventually settled on “Colearning 2.0,” a name suggested by my friend, Mariah Howard. The “2.0” (which we eventually dropped) was a nod to our intention of going beyond the “obvious” ways most tried to design communities of practice.

We also agreed on the following purpose statement:

Create a safe, delightful space where we make our individual work visible to a select group of peers and deepen our learning together.
We think this will help us better achieve our individual goals by:

Exchanging more substantial feedback on the issues we’re facing

Spurring new, creative thinking

Helping us see our individual progress (which, in turn, will help us be more compassionate to ourselves)

Creating a sense of peer support and accountability

Countering the overwhelm we’re all prone to feeling

Bring greater purpose to our work through sharing learning with community

Because we were an odd number and I had already experienced a regular pair checkin with Seb, I decided to do my checkin by email to the whole group.

After eight weeks, one of the pairs had met regularly, the other less so. But the takeaways had been wonderful, and everybody found the experience useful enough that they wanted to continue. We made one small change. Participating virtually with the whole group was not as good as having a partner, so I asked Kate Wing if she would join the experiment as my partner, and she accepted. (Five years later, Kate and I still check in regularly almost weekly. More on this in an upcoming blog post.)

This second phase of Colearning lasted through the end of 2015. We had mixed experiences overall with the checkins. For some (me and Kate included), they went wonderfully. For others, not so much. We experimented with different pairs and formats, I tried this experiment with another group, and I encouraged others to experiment with it on their own. I never found a formula for general peer support that seemed to work for everybody.

However, I walked away with enough confidence in the value of frequent, regular contact, that I began incorporating it into my programs and designs with more narrow purposes, such as Collaboration Muscles & Mindsets. I often faced resistance from participants, who were nervous about the time commitment, but that resistance would start to dissipate almost immediately, and by the end of these programs, many would say that they looked forward to these regular conversations each week.

More importantly, other wonderful things started to emerge with this group. People would often request peer assists about things ranging from the mundane and technical (such as social media) to people’s actual work projects. These were always well-attended and highly valued. Many of us shadowed each other’s work, learning from watching our peers actually doing the work. One person created a shared repository of resources, that many of us still use and contribute to. Another group formed a book club.

We also organized a variety of face-to-face gatherings, ranging from an improv workshop to site visits to hikes and dinners. In September 2014, a group of us organized a one-day, Open Space, peer learning workshop in San Francisco that 20 people attended.

We were a leaderful group by design. There were no officially-sanctioned events, and there was never any asking for permission. People organized things they themselves wanted to participate in, and invited others — including those outside of our little group — to participate.

Perhaps the most gratifying thing that happened was that people started collaborating on work together. This was never an explicit goal of the group, but it was something I hoped would happen. Several people did (and continue to do) projects together, in some cases forming partnerships and collectives.

Toward the end of 2015, we started experimenting with Slack as another way of staying engaged remotely. Soon thereafter, we officially brought the checkin portion of our experiment to a close and migrated from the mailing list to Slack. This brought us to our third and final phase of Colearning, which lasted through the end of 2018.

Slack increased online engagement and also made it a little bit more fun. People also continued to self-organize. In early January 2017, we experimented with a joint retreat for individual visioning and strategizing. We’ve continued doing these twice a year ever since.

All told, 17 people participated in this experiment, with a final count of 13. We started off as a Bay Area group, but we experimented with remote participants, and ended up with people from Chicago, Portland, and Los Angeles.

New Beginnings

I started playing with all of this six years ago because I was afraid of losing what I was leaving — specifically, deep relationships with other colleagues. As a result, I focused my energies on people who were working independently, regardless of how much of their work was specifically focused on collaboration. These different experiments had taken me above and beyond what I had hoped for, and I was enormously grateful.

However, my priorities for community has shifted over the years. I am less concerned about isolation and more concerned about deepening my (and other’s) practice around collaboration, which is more mission-aligned for me.

Late last year, I decided to stop participating in the Colearning experiment. As I assured the group:

Just because I won’t be on a Slack with all of you doesn’t mean I won’t be in community with all of you…. Obviously, I have deep relationships with all of you, and I hope to continue deepening those. I hope to stay in touch with all of you, I plan on continuing my weekly checkins with Kate as long as she’s willing to put up with me, and when I organize practitioner events, you all will be high on my invitation list….

Networks are about relationships. Experiments and more formal structures can come and go, but those relationships don’t go away. I wanted to be clean about my exit from the group, but I also didn’t want us to see that as the dissolution of community. When I left, someone started a new Slack with a different frame. Many of us continue to stay in close touch, and the bi-annual retreats have continued.

Most importantly, we had the opportunity to celebrate what we had done together (and mourn its passing), and I feel free to focus my energies on designing something new and more relevant to what I care most about right now. I’m a little bit scared, as I always am when diving into the unknown, but I’m also excited about creating something new.

Thanks to H. Jessica Kim and Eun-Joung Lee for reading early drafts of this post. This is the third in a series of blog posts about building a network of collaboration practitioners. The others are:

Building a Network of Collaboration Practitioners (February 7, 2019)
A Personal Case Study in Network-Building: Pre-IPO (February 20, 2019)
A Personal Case Study in Network-Building: Selfishness, Frequent Collisions, and my Colearning Experiment (May 7, 2019)
What We Learned from Five Years of Check-ins (May 14, 2019)
Design Sketch for a Network of Collaboration Practitioners (November 14, 2019)

The Secret to High-Performance Collaboration: Slowing Down

At my previous consultancy, we used to spend a considerable amount of time debriefing every engagement, big or small. We were meticulous in our analysis, nitpicking every detail.

Over time, I started noticing a few patterns. First, I realized that our debriefs were largely ineffective, because we weren’t taking the time to integrate what we learned. We needed to be reviewing past debriefs before new engagements in order to remind ourselves of what we had learned and in order to hold ourselves accountable to improvement. Without that additional space, our debriefs were essentially exercises in self-criticism and generating lists, two skills we didn’t need to be practicing.

Second, a few things began to jump out at me as I reviewed our long list of things we could have done better. Almost without fail, when we had “bad” engagements, someone had slept poorly the night before. Or someone had been working while sick. Or someone had forgotten to eat breakfast that morning. (Forgetting to eat was my personal bane.)

We had spent hours and hours and hours debriefing, and this is what we learned:

When we didn’t take care of ourselves, our performance suffered.
When we didn’t take time to remind ourselves of past lessons, we repeated the same mistakes.

One of my mentors, Gail Taylor, is always encouraging me to seek the simplicity embedded in complexity. What I’ve realized over the years is that, when I find it, I often dismiss it. It seems too obvious. There has to be something else.

Slowly, but surely, I’m breaking this habit, and I’m starting to see more clearly as a result. Which brings me to my biggest insight over the past several months.

The best thing we can do to improve collaborative effectiveness is to slow down.

This has been coming up for me over and over again with all of my recent projects and experiments.

I’m currently doing an experiment with the Code for America incubator in trying to help new companies establish good collaborative habits right from the start. PostCode (the company with which I’m working) is working at a startup pace, and they’ve had inevitable challenges as they move through their storming phase.

Fortunately, when problems crop up, they deal with them quickly. In those situations, they’ve often reached out to me about possible toolkits to help them navigate their challenges. My answer has been consistent: Slow down. They haven’t found the time (beyond the work we’ve done with them, which has been too constrained) for critical conversations about organizational strategy, culture, and group dynamics. It’s understandable. They’re under a tremendous amount of pressure, and in those situations, conversations about strategy and group dynamics can feel like a nice-to-have, not a need-to-have.

Last week, I facilitated a practitioners workshop for the Garfield Foundation on collaborative networks. For one of the Open Space sessions, I led a group through the power workout I developed for Changemaker Bootcamp. We had a wonderful, nuanced conversation about power dynamics, and several people asked, “How do we make sure we have more of these conversations with our constituencies?” My response: “The first step is making the time.”

Telling others (or even yourself) to slow down is easy. Actually doing it is hard. We move fast because of external pressures, mindsets, habits, cultural norms, and so forth. We have little control over most of these things, and what little we can control is incredibly hard to change. But there are tricks that I’ve found helpful over the years.

Experiments. Changing habits is hard, and you will likely fail many times. Approaching the challenge of slowing down as a series of experiments helps. As I wrote previously, one of the keys to a successful experiment is to hold yourself accountable to the results. Failure is okay as long as you’re committed to the intention and are actively incorporating what you learn into new experiments.

If you are truly committed to slowing down, write it down. Write, “Slow down,” on a piece of paper, and put it up where you will see it. Actively devise and track experiments that will help you do this, so that you can monitor your progress and see what’s working and what’s not.

For important conversations — whether it be organizational strategy or a project debrief — schedule those in advance as part of your project plan, and track whether or not they actually happen. If they don’t happen, take the time to examine why, and devise another experiment. The beauty of applying an experimental framework is that simply the process of devising and tracking an experiment is an act of slowing down.

Checkins. My former business partner, Kristin Cobble, recently wrote a wonderful piece on the power of checkins. She describes them mostly in the context of meetings as a way to invite participation and to garner a sense of the collective whole. What I’ve learned over the past several months is that they also serve a much simpler, deeper function. They force you to slow down and reflect — even if just for a moment.

Starting last year, I embarked on a simple experiment with my friend, Seb Paquet, who’s based in Montreal and who, like me, works for himself. We decided to check in with each other once a week for an hour over Skype. We didn’t have any agenda. We would simply use that time to have an extended checkin.

We ended up doing two phases, and it served to be tremendously valuable. Not only did it deepen our relationship, it served several practical purposes. We both had an opportunity to give each other feedback on our respective projects. We supported each other when we faced challenges and cheered each other when we succeeded. The most interesting thing to happen was that, even when things got tremendously busy for both of us, we both stayed very committed to these checkins. They were not just nice-to-have; they were helping us work more effectively.

Inspired by these results, I invited my colleagues Pete Forsyth, Rebecca Petzel, Odin Zackman, and Amy Wu — who all work independently — to participate in a similar experiment earlier this year. We wanted to experiment with ways that we — as an informal network — could achieve the same (or better) benefits that people get from working in great organizations. In particular, we wanted to be more intentional about learning from each other. We called our experiment, Colearning 2.0, a play on the coworking movement.

We explored several things that we could do together, but we settled on doing weekly pair checkins, as Seb and I had done beforehand. There was some reluctance at first. One thing we all had in common was a frequent feeling of overwhelm, and taking an hour out of our week to “just talk” seemed burdensome. Not only did everyone end up finding the experience valuable, there’s a desire to continue the practice and take it to the next level.

I recently spoke with Joe Hsueh about his recent trip to Istanbul. One of the things that struck him the most about his trip was the adhan — the Islamic call to prayer. Imagine being in a bustling city of 14 million people where every day, at prescribed times, a horn sounds and the entire city goes silent. Imagine what it feels like to have that regular moment of collective, silent reflection.

I believe that checkins could be a powerful keystone habit that helps us slow down overall, which ultimately helps us collaborate more effectively. This is a hypothesis I continue to explore.

What helps you to slow down? What’s been the impact of doing so?