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.

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)

A Personal Case Study in Network-Building: Pre-IPO

Last week, I shared a preamble on my plans to build a network of collaboration practitioners. Given the high-level nature of my post, I was surprised by the reaction and strong interest, especially on LinkedIn . I think it spoke to two things. First, despite all of our connectedness on social media, people crave deeper community. Second, it’s easy to be enthused about something when it’s described in a high-level, hand-wavy way. In this and subsequent posts, I’m going to try to get less hand-wavy by sharing actual experiences. I want to start by sharing my first “formal” experience building a network over 20 years ago.

In 1998, I made the difficult decision to leave the only full-time job I had ever known (and, to this day, the only time I’ve ever worked for someone else). I loved my boss and my team, and I liked the work, but I didn’t love it. I wanted to do something that I loved.

The problem was that I had no idea what that was. Or at least I had no idea how to get paid doing it. My default solution was to start my own company, which was one of the reasons I had moved to the Bay Area in the first place. But I didn’t have an idea that felt compelling. I decided to give myself a year to figure it out, marking the date when I would give notice in my calendar.

One of the things I love about the Bay Area is that it’s a physically small space where lots of interesting people live, which means that serendipitous collisions are common. This structure complements Silicon Valley culture, where people really value relationships. This culture manifests in a wonderful and a not-so-wonderful way. On one side of the spectrum, there is this wonderful openness, where people are willing to grab coffee with just about anyone — even “competitors” — to talk excitedly about their work and passions. On the other side, there are a plethora of networking events largely attended by drive-by networkers — people who treat relationships as a kind of game where they try to spread and collect as many business cards as possible.

I figured that a simple next step in my quest to figure out what to do with my life would be to go to some of these networking meetings. However, the thought repelled me. I wanted to spend quality time meeting interesting people doing interesting things. Going to a networking meeting felt like a painful and inefficient way to do this.

Then I had an epiphany. I was lucky enough to already be friends with some interesting people doing interesting things. Rather than try to meet new people, I decided to make up an excuse to hang out with the people I already knew (and liked). I invited a few friends to my apartment to eat pizza and “help me figure out what to do with my life.” We didn’t solve my problem that night, but I learned a lot about their work and hopes and dreams, I got a lot of encouragement, and I had a good time. In retrospect, it was an obvious thing to do, but I had never thought of doing it before, and I was hungry to do it more.

I decided to expand my invitation list to about eight people and do these dinners monthly. I wanted to keep the gatherings intimate, but I also wanted to open up the group to others. I decided to do two things to address this tension.

First, we decided to call the group, “pre-ipo,” a nod to our shared interest in startups.

Second, I established two ground rules. The first was, “shameless self-exploitation.” My reasons for forming this group were completely selfish. I wanted to figure out what I was going to do next, and I wanted to hang out with fun, interesting people in the process. I wanted to be clear about my own selfish intentions, but I also wanted others to be similarly selfish. This first ground rule made it clear that it was not only acceptable to want to get something out of participating, it was required.

The second was, “The Eugene Rule.” I had to like you for you to be part of the group. I also assumed a transitive property of relationships. In other words, if you liked someone, and if you thought I would like that person too, it was highly likely that you would be right. Rather than act as a gatekeeper, people were welcome to invite others, no questions asked, as long as they were confident that these others would pass The Eugene Rule.

As it turned out, these two ground rules, along with a strong initial set of relationships, helped create the balanced culture that I sought. It enabled all of us to explore our “selfish” goals while developing deep, authentic relationships with each other.

Every month, someone would do a deep dive into their work. One person was building online community tools. Another was building GPS-powered pedometers. (Remember, this was the 1990s, well before smartphones.) Another had developed a Palm Pilot app (again, it was the 1990s) for doctors to write prescriptions, so that pharmacists didn’t have to try to interpret their notoriously bad handwriting. My favorite was when one person described his experiences starting a hip hop music label.

I never paid for space. We always managed to find people to host for free simply by asking. After the talks, we would eat pizza and hang out. We generally had about a dozen people every month, with about 25 people at our largest gathering. Many people ended up partnering with others, in some cases joining each other’s boards. More importantly, people felt comfortable letting down their guard, which led to lots of real friendships being formed.

After nine months of doing these gatherings, I still had no idea what I wanted to do next. However, engaging with this community helped me realize that I didn’t have to decide right away, that I could put myself out there as a consultant and continue to explore, a decision that eventually led to the work I’m still doing today over two decades later.

I often think fondly about pre-ipo. My only regret is that I have no photos or any other form of (easily findable) documentation from that time. It was well before digital cameras, much less smartphones, and I also didn’t value documentation or leaving trails as much as I do now. Regardless, it was a wonderful, generative time, and it also helped me better understand some underlying principles for building networks, principles that I think are often undervalued in other efforts. Specifically:

Be clear about what you want. I often see groups wrestling with questions about governance and structure without voicing what they actually want. With pre-ipo, I had a clear goal that was embodied in the group’s name, which made it clear to others too.

Avoid premature and unnecessary structure. We started small, and we assumed high trust, which meant that we were able to be open without having to worry about complicated membership or governance rules. Instead of worrying about structure or scale, we focused on developing a warm culture that encouraged us to form deep, authentic, generous relationships.

Assume abundance! There were already plenty of formal entrepreneur networks in Silicon Valley, but I didn’t want to participate in any of those. That was fine! There doesn’t have to be only one group for a particular purpose, and in truth, there never actually is. Every person in pre-ipo already belonged to other entrepreneur networks, both formal and informal. Being part of multiple networks benefited everyone, because it gave all of us access to more people and broader learning.

Having an abundance mindset also made our first ground rule, “shameless self-exploitation,” work. I often see groups unintentionally develop a culture of martyrdom, where people feel obliged to sacrifice whatever individual desires they have for the “greater good.” This reflects a zero-sum mindset where people assume that their individual goals come at the expense of other people’s, and it results in spaces where people feel timid and fear stepping on each other’s toes. We assumed that our individual goals would complement and reinforce each other’s, which created a liberating and generative space.

This is the second 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)

Building a Network of Collaboration Practitioners

Most groups have at least one person who is motivated to help their group get better at collaboration, regardless of their role. I call these folks, “collaboration practitioners.” They are the people I am most interested in empowering and supporting. The more I can help them, the more groups I can impact.

In order to support collaboration practitioners, I need to find them. “Collaboration practitioner” is not everyday parlance. Most people have no idea what I’m talking about when I use this term. Moreover, many people who play this role are not doing it formally. It’s not in their job description, and they may not even realize they’re doing it.

Self-awareness is the first step. It’s hard to seek help if you don’t have a name for what you’re doing. Having that name makes it easier to find and learn from others who play similar roles.

In the past, I’ve played a small role in connecting collaboration practitioners with each other. For the most part, it’s been a selfish endeavor. When I first got started in this business, I was desperate to find and learn from other practitioners. When I started finding them, I held onto them for dear life. It took me several years before I stopped feeling isolated. Ever since, my community has been an invaluable support structure.

Weaving some of these relationships together came naturally to me. After all, it’s one of the muscles needed to be great at collaboration. At the same time, I intentionally shied away from spending too much time doing this. I wanted to focus on going deeper, not broader.

This year. I want to invest more of my time building a network of practitioners. 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.

The beauty of trying to model network principles in my own field rather than for a client is that I have fewer constraints. I can be much more creative about what I do and how I do it, and I can be much more candid about my experiences.

Sometimes (hopefully more often than not), I’ll be successful. Other times, I won’t. I want to show both. This work is hard. Pretending that it’s not is not only dishonest, it’s a disservice to those of us trying to learn and improve.

I’ll start by sharing a series of blog posts over the next few weeks about past experiences, surfacing and exploring important principles through these stories. I’ll then start sharing what I’m thinking and doing about this new network. A lot of those posts will be half-baked, because… well, these things take a while to bake. I hope that this half-bakedness serves as an invitation, an opportunity for you to shape this network as well through your thinking, ideas, and participation.

This is the first 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)

The Secret to a Good Retrospective? Actually Having Them!

People often ask me how I structure retrospectives — meetings where a team debriefs and harvests its learning. As with all of my techniques, I am happy to share, and my framework and template is freely available on this website. As a process geek, I love exploring the art of leading good retrospectives. But when it comes to most groups, I prefer talking about some of the more mundane aspects of retrospectives.

Scheduling them, for example.

First, a story. One of the hardest, most time-consuming problems in software development is finding bugs — mistakes in the software’s code. Bugs are inevitable, and fixing them takes up large chunks of a programmer’s time. When I worked in tech over 20 years ago, I met with a vendor that had an extraordinary debugging tool. It would analyze your code and automatically spit out a list of bugs. It wasn’t doing anything magical, it was just clever automation of some oft-practiced techniques.

I was blown away by the simplicity of what they had done. I asked them how others were receiving their tool, figuring that it was selling through the roof. The representative furrowed his brow and responded, “Most people don’t react positively.”

“Why?” I asked in surprise.

“When we demo our tool,” he explained, “we ask people to point it at their actual software, so that it’s working with real data. When it starts spitting out bugs, people start freaking out. They don’t have the resources to fix all of the problems it finds before their scheduled release. They’d rather not know about them.”

It was hard for me to fathom at the time, but as I spent more time in tech, I started seeing this for myself. As I transitioned out of tech into organizational work, I started seeing this manifest in a different way.

Simply put, in my experience, most teams never schedule retrospectives. If we’re being honest with ourselves, I think this is because most of us are afraid of what we might discover. Maybe we’re worried about our ability to fix the problems. Or maybe we’re afraid of negative feedback and challenging conversations. Either way, what it boils down to is that getting better has to wait… possibly forever.

When we do schedule them, they are often the first to get canceled when things get busy, which for most groups is always. I say this with the utmost humility, because this is absolutely true of me. I try really hard to be disciplined about doing them with my teams, and I’m probably better than most. But that’s not saying much, because the bar is really low, and my track record is mottled with canceled meetings.

Perhaps you’ll understand why, then, if you ask me how to lead a successful retrospective, I will often respond, “By scheduling one.” I’m not being facetious. If you’re actually having retrospectives, you’re already doing better than most.

Scheduling them, unfortunately, is only step one. Step two is integrating what you learn. As I wrote last week, people forget things at an exponential rate. It doesn’t matter how artfully you facilitate your retrospective if you’re not building in time to review what you learned, because you will likely forget all those lessons anyway. If you can’t remember what you learned, you’re not going to have anything to integrate. What’s the point of learning if you’re not integrating those lessons?

Step three (which is actually step one) is aligning around goals and success as a group. If you haven’t aligned around goals and success at the beginning of the project, then how can you assess how well you did? For most groups, the answer is generally that whoever has the power gets to decide. There’s no accountability to actual results, because you haven’t decided as a team what you were aiming for. It’s too easy to rationalize anything as success.

If you’re truly serious about learning and improving, then you are, at minimum:

  • Aligning around goals and success as a group
  • Having retrospectives
  • Taking time to review and integrate what you learn

Make sure these are on your calendar, and protect those times.

Photo by Cathy Haglund. CC BY-NC 2.0.

Planning Isn’t Helpful If You Can’t Remember Your Agreements

When my friend, Kristin Cobble, and I founded Groupaya, my previous consulting firm, in 2011, one of our goals was to model the best practices of high-performing groups. We didn’t want to just help other groups develop these skills and habits. We wanted to show what a high-performance group looked like.

One habit we were sure we’d adopt was making time to talk together about strategy and culture. In our planning stage, our associate, Rebecca Petzel, facilitated us through a number of important conversations, including one about our values. We eventually converged on six words that we thought best represented our most important shared values.

I was proud, even smug about the time we had invested in this work. In my mind, we were modeling what it meant to be a values-driven company. So I was taken aback when, six months later, Rebecca asked us if we could name our six values, and both Kristin and I could only name four between us.

What was the point of coming up with a list of values if we couldn’t remember what they were?

Entrepreneur and investor, Marc Andreessen, once said, “The process of planning is very valuable, for forcing you to think hard about what you are doing, but the actual plan that results from it is probably useless.” In some ways, this was true for us. Because of the conversations we had had with each other, we were more aligned, and we understood and trusted each other more. Furthermore, even though we didn’t remember all six of our words, we still cared deeply about each and every one of those values, and our work reflected this. How your values come through in your actions is the point of values work, not the list itself.

However, what if we hadn’t been living the values that we had named? How would anyone have known? The problem wasn’t that we couldn’t remember our six words. The problem was that we weren’t constantly thinking together about them, talking together about them, reflecting together on what it meant to live them. We weren’t holding ourselves accountable to our values, because we weren’t taking the time to assess ourselves. We were making it hard to stay aligned around our values, because we weren’t taking the time to talk about what this meant and why it was important.

I was embarrassed, but I also knew that we weren’t alone. Donald Sull, a senior lecturer at MIT’s Sloan School of Management, asked middle managers at over 250 companies to list their companies’ top five strategic priorities. Half of them could not even remember one. Only a third could remember two. Even worse, only half said they understood the connections between their companies’ priorities and initiatives. They had seen the priorities plenty of times — almost 90 percent said that top leaders communicated the strategy frequently enough. Those who remembered them just didn’t understand them.

Once we recognized the problem, we were able to fix it. But I’m amazed by how many leaders and consultants make the same mistakes that we made… and keep making them. It starts by understanding what the mistakes are.

The first mistake is not making time for the whole team to talk about strategy and culture.

The second mistake is assuming that your work is done after one meeting.

My colleague, Catherine Madden, made this wonderful video last year about psychologist Hermann Ebbinghaus’s pioneering research around memory and the “Forgetting Curve” for Edutopia.

The brilliant Nicky Case took these concepts even further in this interactive explanation of how you counter the Forgetting Curve. I highly recommend that everyone look at both, but I’ll summarize their key points here:

  • In the 1880s, Ebbinghaus found that — without any reinforcement — we forget what we learn or hear at an exponential rate. After just one hour, we will already forget half of what we’ve learned. After one day, we will forget two-thirds.
  • There are a number of ways to counter this. The basic one is to reinforce what you learn. But you have to do it quickly, and you have to do it repetitively, because doing it once only slows down the curve. (Explore Nicky’s explanation of spaced repetition to understand this more deeply.)
  • Some methods are more effective at reinforcing than others, specifically peer learning and visualizations.

Given this, what’s the right way to do strategy and culture work? The first step is to create space for the whole group to discuss strategy and culture. However, if all you’re doing is scheduling one meeting, you’re doing it wrong, regardless of how expertly you design or facilitate it. You also need to:

  • Write down the agreements from the meeting. Bonus points if you use pictures. More bonus points if the participants themselves draw the pictures. (As an aside, this also applies to next steps and decisions made at any meeting. If you don’t write them down, they might as well not have happened.)
  • Make sure everyone knows where the agreements are. Put them somewhere where everyone will see them often. (Again, this also applies to next steps and decisions made.) My colleague, Rachel Weidinger, has a great trick with remote teams. She’ll have her teammates print their agreements, post them somewhere near their workspaces, and take and share photos of where they put them so that everyone else knows that they’ve done this. It creates accountability, and it also lets people see each other workspaces, which has other benefits with remote work.
  • Schedule followups at the same time as you’re planning your meeting. These could take many forms. They could be pair conversations, they could be designated time at the beginning or end of regular standup meetings or checkins, they could be regularly scheduled reviews of the artifacts, etc. Be creative — they don’t have to be meetings. What matters most is doing these repetitively and frequently.

None of this is easy. Doing them doesn’t mean that you’ll succeed, but not doing them guarantees that you’ll fail.