Design Sketch for a Network of Collaboration Practitioners

Earlier this year, I announced that I wanted to build a more formal network of collaboration practitioners. I wrote:

It’s always been an important part of my strategy, and it feels like the right moment to prioritize it.

I also want to be open and transparent about how I’m trying to do it in order to model network principles. As the field has professionalized, I’ve felt a narrowness in how many practitioners interpret and practice network principles. I want to offer a counter to this.

In subsequent blog posts, I shared what I had learned from previous experiences. In my first case study, I pulled out the following principles:

  • Be clear about what you want
  • Avoid premature and unnecessary structure
  • Assume abundance!

In my second case study, I pulled out a few more principles:

  • Be selfish, but in a networked way
  • Frequent collisions
  • Networks are about relationships

In this post, I want to offer a few more driving principles and outline how I’m currently thinking about pulling this all together.

Inspired by Alcoholics Anonymous

In addition to my previous work, one of my biggest inspirations for how I want to design this is Alcoholics Anonymous (A.A.). A.A. is a global, open, decentralized, self-organizing network that emphasizes pair relationships and peer support, and it has helped thousands of people over the years, including a few whom I know. The core of its program is its 12 steps, the first step of which is admitting you have a problem. Anyone can start an A.A. support group. It simply requires “the need for one as expressed by at least two or three alcoholics; the cooperation of other A.A. members; a meeting place; a coffeepot; A.A. literature and meeting lists; and other supplies.”

I love how open, clear, and simple the platform is. There are formal structures to help keep this all organized, but the basic model is to encourage motivated people to take action. Furthermore, there is a deeply embedded culture of support and practice. This is not dictated by the structure, but it’s reinforced by it. The structures themselves are simple, even though the work of living with addiction is not.

I’ve always been taken by A.A.’s model and results. I also think that what many collaboration practitioners (including me) need amounts to self-help. Most of us are not working in structures that are conducive to our work. Many of us are not doing this work as part of our official roles within our groups, which means it often comes on our own time, and the work is often unseen and undervalued. When structure and culture is working against you, it’s even more contingent for you to maintain disciplined habits and to find support where you can.

I think a lot of collaboration practitioners already find ways to do this on our own, especially the peer support part. However, I think our default culture prevents us from truly getting what we want. I think we generally don’t ask for as much time as we need (and that others would happily provide, because it would benefit them too), and I think we’re generally not as open or transparent about what we’re learning as we could be.

What I Want

I want to create a support group for collaboration practitioners focused on developing and maintaining good habits, the kinds of habits that will not only make us better practitioners, but also enable us to live happy, healthy, sane lives. (These two things are inextricably intertwingled in my opinion.)

I want us to be focused on depth over breadth — deep practice, deep sharing, deep relationships. I want all of us to have a sense of what’s going on with each other professionally and personally. I want there to be enough trust and shared understanding and language that we all feel comfortable throwing around crazy ideas or asking for help. I would love to see participants collaborate, but only when it’s compelling. I’m not interested in collaboration for collaboration’s sake.

I want it to be an open group, but I also want it to feel intimate. I assume this means that it needs to be small, which may require limiting the size of the group, but I don’t know what the limit should be or whether this assumption is even true. I want participants to share what they learn from each other more broadly while also being thoughtful and respectful of people’s privacy and safety.

In other words, I don’t just want this to be a group of folks we already know and are comfortable with. I want to see diversity in as many dimensions as possible — age, gender, race, job, etc. This suggests paying particular attention to diversity and mobility (people moving in and out) with the initial group and letting it evolve from there.

I want participants to feel ownership and agency over their experience in the group. I want it to be leaderful and bold.

Finally, I want to create structures and practices that are easily replicable and customizable, I want to invest in the culture and capacities that can lead to success, and I want to share everything that I learn in the process. I’d love to see many, many, many groups copy what we do, customizing it as they see fit, and openly and frequently sharing what they learn so that we all may benefit. These groups could share a common “brand” or identity, like A.A., but it’s not that important to me. What matters more is that these types of spaces for collaboration practitioners to support each other are abundant.

Design Sketch

Given all of the above, here’s what I’m thinking (and have already started to experiment with). The group (as yet unnamed) would be centered around supporting each other with these Habits of Effective Collaboration Practitioners:

  1. Admit you are a collaboration practitioner.
  2. Breathe.
  3. Start with you.
  4. Listen and understand others.
  5. Be intentional, and hold it lightly.
  6. Stretch, but don't hurt yourself.
  7. Be compassionate.
  8. Do the work.
  9. Pick yourself up.
  10. Celebrate!
  11. Reflect and integrate.
  12. Share!
  13. Repeat.

Most practitioners already do some subset of these regularly. Our goal would be to support each other in doing all of them, which would help all of us become better practitioners and people. (I’ll blog more about this list later, as I’m still eliciting feedback and making changes. I’d love to hear your reactions in the comments section below. Many thanks to Anya Kandel, Travis Kriplean, Eun-Joung Lee, Danny Spitzberg, Matt Thompson, and Kate Wing for providing early feedback.)

Everyone participating would go through an on-boarding process that would include reviewing these habits and talking one-on-one with at least two current participants. This would help people feel more welcome, and it would remind everyone that networks are fundamentally about people and relationships and that we encourage people to forge their own individual connections beyond the platform.

Beyond the on-boarding, there would be only one required activity (which would take place on a Slack instance set up for this group) — checking in every week. The checkin could be brief, and the prompt could change over time, but the basic idea is that everyone would share what was going on in their work and lives at least once a week.

This simple practice would accomplish several things:

  • Make it clear whether you’re in or out. (More on this below.)
  • Help people learn how to use and get comfortable with the platform
  • Build community and relationships through frequent, but lightweight engagement
  • Establish a rhythm that makes the community and the space feel alive
  • Support participants in developing core collaboration and network muscles, especially our Sharing muscles.

I want to make it both simple and clear to delineate between those participating in this network and those who are not. If you’re willing to go through the on-boarding, agree to some basic community agreements, and check in regularly, you’re welcome to participate. I also want to make it okay not to participate. This structure may not feel right for some, or it may not be the right group of people, or it may be asking for too much time. Just because you’re not participating in this particular network doesn’t mean you can’t (or don’t) have a relationship with me or other participants. If you stop participating for whatever reason, that’s okay too, and you’d be welcome to return by just going through the on-boarding again.

I’m also making a bet about our Sharing muscles. When it comes to sharing, most of the practitioners I’ve met default to sharing only when they’re face-to-face with others and in larger, more "finished" chunks. There’s nothing wrong with this. However, many of the interesting and desirable things that sometimes emerge from networks require more frequent and open sharing. Rather than hoping this happens organically, I want to actively cultivate this muscle by encouraging participants to share rough little tidbits about their work and their thinking more frequently. My hope is that developing this one keystone habit will help unlock all sorts of other desirable muscles and mindsets — pausing, working iteratively, comfort sharing rough work, vulnerability, celebration, etc. — which will both help all of us individually as practitioners and the network as a whole.

Finally, I want to encourage (but not require) participants to find a regular checkin partner, similar to my experiences with Kate Wing over the past five years.

I’ve been experimenting with some of these ideas and structures over the past year, and I’m looking forward to taking another step forward. (Many thanks to Cherine Badawi, Shirley Huey, Anya Kandel, Travis Kriplean, Adene Sacks, and Zoe Tamaki for playing.) I have lots of open questions, and I’m looking forward to exploring these.

I’m not ready to open it up to everyone just yet. I want to be really intentional about establishing the culture and practices with a core group, and I want to make sure that we have a good balance of emerging and experienced practitioners. That said, if you think you might want to play, please either leave a comment below or send me an email directly. If you want to try to start your own group stealing any or all of this, please do, and please let me know, as I’d love to learn from your experiences! Finally, if you have any other thoughts on any of this, please leave a comment below. This is a work-in-progress, and I’m looking forward to continuing to share what I learn.

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

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

What We Learned from Five Years of Check-ins

Eugene and Kate

Eugene and Kate

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:

  1. Building a Network of Collaboration Practitioners (February 7, 2019)
  2. A Personal Case Study in Network-Building: Pre-IPO (February 20, 2019)
  3. A Personal Case Study in Network-Building: Selfishness, Frequent Collisions, and my Colearning Experiment (May 7, 2019)
  4. What We Learned from Five Years of Check-ins (May 14, 2019)
  5. 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:

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

Do-It-Yourself Strategy and Culture

Biker

In 2009, I was asked by the Wikimedia Foundation to design and lead a movement-wide strategic planning process. The goal was to create a high-quality, five-year strategic plan the same way that Wikipedia was created — by creating a space where anyone in the world who cared could come and literally co-author the plan.

We had two fundamental challenges. First, it wasn’t enough to simply have a plan. It had to be a good plan that some significant percentage of the movement both understood and felt ownership over.

Second, we were asking people in the community to develop a strategy, but most people had no idea what strategy was. (This, frankly, is true of people in general, even in business.) It was different from Wikipedia in that most people already have a mental model of what an encyclopedia is. We had to be more concrete about what it was that we were asking people to do.

I explained that strategic planning, when done well, consists of collectively exploring four basic questions:

  • Where are we now?
  • Where do we want to go? Why?
  • How do we get there?

I further explained that we were going to create a website with these questions, we were going to get as many people as possible to explore these questions on that website, and by the end of the year, we would have our movement-wide, five-year strategic plan.

And that’s essentially what we did.

Get the right people to explore core questions together. Where are we now? Where do we want to go, and why? How do we get there? Provide the space and the support to help these people have the most effective conversation possible. Trust that something good will emerge and that those who created it will feel ownership over it.

This is how I’ve always done strategy, regardless of the size or shape of the group. It looks different every time, but the basic principles are always the same. People were intrigued by what we accomplished with Wikimedia, because it was global and primarily online, because we had gaudy results, and because Wikipedia is a sexy project. However, I was simply using the same basic approach that I use when working with small teams and even my own life.

The craft of developing strategy is figuring out how best to explore these core questions. It’s not hard to come up with answers. The challenge is coming up with good answers. To do that, you need to give the right people the opportunity and the space to struggle over these questions. That process doesn’t just result in better answers. It results in greater ownership over those answers.

Breakfast and Culture

What’s your strategy for eating breakfast in the morning?

Are you a grab-and-run person, either from your own kitchen or from a coffee shop near your office? Eating breakfast at home is cheaper than eating out, but eating out might be faster. Are you optimizing for time or money? Why?

Maybe you have kids, and you value the ritual of kicking off the day eating together? Maybe you’re a night owl, and you’d rather get an extra 30-minutes of sleep than worry about eating at all in the morning.

Where do you want to go? Why? How do you get there? These are key strategic questions, but you can’t answer them without also considering culture — your patterns of behavior, your values, your mindsets, your identity. Choosing to cook your own meals is as much a cultural decision as it is a strategic one.

In my past life as a collaboration consultant, groups would hire me to help with either strategy or culture, but never both. I realized fairly quickly that trying to separate those two processes was largely artificial, that you couldn’t explore one without inevitably colliding with the other.

Peter Drucker famously said, “Culture eats strategy for breakfast.” He did not intend to say that one was more important than the other, but that both were necessarily intertwined. Or, as my friend, Jeff Hwang, has more accurately put it, “Saying culture eats strategy for breakfast is like saying your left foot eats your right foot for breakfast. You need both.”

As with strategy, culture work is a process of collective inquiry, except instead of focusing on action (where do you want to go?), the questions are centered around identity:

  • Who are we now?
  • Who do we want to be, and why?
  • How do we get there?

The key to effective culture work is to explore these questions yourself, to struggle over them together as a group, and to constantly revisit them as you try things and learn.

DIY Strategy and Culture

Toward the end of 2013, Dharmishta Rood, who was then managing Code for America’s startups program, asked me if I would mentor one of its incubator companies, which was having some challenges around communication and decision-making. I had been toying with some ideas for a do-it-yourself toolkit that would help groups develop better collaborative habits on their own, and I suggested that we start there.

We immediately ran into problems. The toolkit assumed that the group was already aligned around a core strategy, but with this group, that wasn’t the case. They had been going, going, going without stopping to step back and ask themselves what they were trying to accomplish, how they wanted to accomplish those things, and why. (This is very typical with startups.)

This group needed space to do some core work around strategy and culture. I threw out my old toolkit and created a new one designed to help groups have strategy and culture conversations continuously and productively on their own. The revised toolkit was based on the key questions underlying strategy and culture depicted as two cyclical loops:

Strategy / Culture Questions

While most strategy or culture processes are progressively staged, in practice, inquiry is never linear, nor should it be. Spending time on one question surfaces new insights into the other questions, and vice-versa. Where you start and the order in which you go are not important. What matters is that you get to all of the questions eventually and that you revisit them constantly — hence the two cycles. My colleague, Kate Wing, recently noted the resemblance of the diagram to bicycle wheels, which is why we now call it the Strategy-Culture Bicycle.

Dharmishta and I saw the Bicycle pay immediate dividends with this group. People were able to wade through the complexity and overwhelm, notice and celebrate what they had already accomplished, and identify high-priority questions that needed further discussion. Furthermore, the process was simple enough that it did not require a third-party’s assistance. They were able to do it fine on their own, and they would get better at it as they practiced.

Pleased and a bit surprised by its effectiveness, I asked my long-time colleague, Amy Wu of Duende, to partner with me on these toolkits. We prototyped another version of the toolkit with four of last year’s Code for America accelerator companies, and once again, saw great success.

We’ve gone through eight iterations together, we’ve tested the kit with over a dozen groups and individuals (for personal and professional life planning), and we’ve added some complementary components. A number of practitioners have used the toolkit on their own to help other groups, including me, Dharmishta, Amy, Kate, and Rebecca Petzel.

I’m thrilled by the potential of toolkits like these to help build the capacity of practitioners to act more strategically and to design their aspired culture. As with all of my work, these toolkits are available here and are public domain, meaning that they are freely available and that you can do anything you want with them. You can also purchase pre-printed packages.

Please use them, share them, and share your experiences! Your feedback will help us continuously improve them.