checkins – Faster Than 20

From Go-Go-Go to Going Slow: Lessons from My Own Painful, but Ultimately Successful Journey

I discovered weights freshman year in college, and as a weak and skinny kid, I found them to be a revelation. One of my friends had played football in high school, and he and I would work out together often. He worked out hard — at least five days a week — and I liked his routine, so I adopted something similar.

I rapidly gained strength, but I also peaked quickly. Naturally, I tried working out more, but it didn’t seem to help. I maintained more or less the same routine throughout my sophomore year without any significant gains, which I found frustrating and demotivating. It led to long stretches where I would stop working out altogether.

Junior year, I restarted my workouts, and again saw little progress. My next door neighbor that year turned out to be a serious bodybuilder. One day, I asked him for advice. I started by telling him how much I worked out, and he cut me off. “You’re working out too much,” he said. “Your body needs rest to recover and build muscle. Try doing 45 minutes three days a week.”

“Are you sure?” I asked incredulously. Everything he said made sense except for his specific recommendation, which amounted to half as much as I had been doing for years.

“Try it,” he insisted.

I did. After just a few weeks, I saw marked improvement for the first time in over a year. I was floored. It turned out that, in order to get stronger, I just had to do less.

The Power of the Pause

I am often approached by groups with go-go-go cultures asking how to:

Build trust and morale
Work together more strategically
Learn via experimentation
Align their structures and behaviors with their desired values and culture (often, these days, with a focus on equity)

When I hear more about their current situations, I often find myself channeling my bodybuilder friend. You can't do any of these things if you aren't regularly slowing down to pause, to:

Reflect together
Listen deeply to each other
Have hard conversations with each other
Make adjustments
Rest and recover

If you're not committed to developing your muscles around pausing, you not only will not succeed at any of the above, you may even hurt yourselves.

When my friend told me to try working out less, I was more than happy to try, even though I was skeptical. When I tell other collaboration practitioners they need to practice pausing, I get the same skepticism, but none of the joy. There are reasons why they are go-go-go, and trying to shift those habits and mindsets is not only very hard, it can be downright anxiety-inducing.

I know this all too well. For the first dozen years of my career as a collaboration practitioner, I was the worst perpetuator of this go-go-go mindset. It took me six years of consistent effort and constant failure along with a health scare to learn how to slow down. It's made me a better person and a better practitioner, and it's also made me tremendously empathetic to others who are suffering from similar afflictions.

I blogged a lot about my journey as I was going through it, both on my personal blog and on this one. I also shared a tool — my Self-Care Dashboard — that ended up being enormously useful. But I never bothered writing about how I eventually turned a corner, how I've been able to sustain this balance, and the impact it's had on my life and my work. I'd like to correct that here, both to complete the record and also hopefully to offer actionable encouragement to other practitioners dealing with this challenge.

Developing Bad Habits

The first thing to know about my go-go-go ways is that I wasn't always this way. I was capable of tremendous focus and endurance, especially when it came to things I was passionate about, but I also valued my chill-out time. My childhood was spacious and wonderful, full of time to think, explore, and zone out. My first few years after college were similar, which enabled me to realize my passion for collaboration as well as to develop some initial practices.

My lifestyle started to change for the worse when I cofounded my first collaboration consultancy in 2002. I was extremely fortunate to have a mentor who taught and encouraged me and a cofounder with whom I could play and learn. But I was also in my 20s with no formal experience and a job description that I had more or less made up. Moreover, we were trying to make do in a down economy.

Needless to say, business was not good. I went into debt and barely scratched a living for several years before things slowly started turning around. It was stressful and unhealthy, and even though I was barely making any money, I found myself working all the time. I was also young and single, and I suffered a bit from the Silicon Valley mindset that idolatrized struggle before success. I thought I was simply paying my dues, like any good entrepreneur or changemaker, and if business ever got better, I promised myself that I would return to my more balanced ways. Unfortunately, I was not precise with myself about what "business getting better" looked like, and my difficult habits and scarcity mindset continued to perpetuate themselves.

In 2009, three things converged, causing me to finally reconsider my ways. First, I experienced the painful end of a long relationship. Second, I was massively burned out. Third, my then four-year old nephew, whom I adored (and still adore), came to visit San Francisco for the first time ever, but I was so busy that week, I barely spent any time with him. I was extremely upset about this, and it caused me to reflect deeply on what I was doing and how I could change.

First Steps

One of the first and best things I did was to hire a coach. She helped me to articulate a clear vision of what a balanced life looked like for me. Put simply, all of the best, most balanced times of my life had three things in common: basketball, books, and lots of time with family and friends. Imagining a life replete with these three things made me feel light and happy, and they became my personal North Star.

The next step was to understand what, professionally, was preventing me from having these things. Two answers quickly came to mind: Bad habits perpetuated by a fear of not making enough money and a constant feeling of isolation. I was lucky to have community, but what I needed were colleagues. If I could make more money, and if I felt like I was part of a team, I thought I might take a break every once in a while, which would hopefully and eventually lead to me to my North Star.

I still had more questions than answers, but I made two concrete changes as a result of my coaching sessions. First, I raised my rates for the first time in seven years. More money, I reasoned, would give me more space. I considered myself to be one of the top people in the field, and I had known for years that my rate was not commensurate with others, but my deeply engrained fear of not getting enough work had prevented me from raising them earlier.

Second, I decided that I would never take on another complex systems change project without an equal partner. This decision both thrilled and terrified me. On the one hand, I craved partnership. On the other hand, it meant that I wasn’t just raising my rates, I was essentially raising and doubling them. Would I ever get any work again? I believed, in my head, that I would. I had seen others do it, so I knew it was possible, but I was still really scared.

Fortunately, I was able to test these changes almost immediately. The CIO of a Fortune 100 company approached me about some possible work. He fit the profile of a lot of past clients, in that he had tried working with a few traditional (and very expensive) management consulting firms, he had been dissatisfied with their results, and he was looking for something more outside-the-box. He was already talking to some prestigious design firms, when a colleague mentioned me as a possible candidate.

I felt excited about the possibility of working with him, I knew that budget was not going to be an issue for him the way it might be for a smaller organization, and I already had someone in mind with whom I wanted to partner. I thought my chances of getting the work was low, which emboldened me to really go for it — to put together a team of folks with whom I really wanted to work and to propose what I felt would be the ideal project without constraining myself. When I put together my budget, I could feel my palms sweating and my heart beating. I had managed projects with large budgets before, but I had never before written a proposal for that large a sum of money.

Somehow, we got the work! He and his team turned out to be dream clients, and a few members of the team I had pulled together became the core of the consulting firm I cofounded one year later.

After we secured a verbal agreement with our client, we had to work through some bureaucracy. I had been planning a vacation a few months in advance, but as the date approached, we had still not agreed on an actual contract, and I felt old anxieties cropping up. I strongly considered canceling my vacation, but my partner insisted that she had everything under control and that I should not only go, but fully disconnect while I was gone. I listened to her, and everything worked out. The structures I had created and the people with whom I had surrounded myself liberated me to take my vacation, my first in eight years.

Falling Over and Over Again

I felt relaxed for the first time in my career, and it was showing in the work. I was excited about new opportunities, and I loved everyone with whom I was working. More importantly, my life was feeling more spacious. I thought I had turned a corner. Unfortunately, I had confused taking a few steps with walking. I still had a lot of inner and outer work to do, and — as it turned out — I was going to have to fall a lot more along the way.

Things started getting out of balance again when a few of us decided to formalize our partnership. We spent a lot of time thinking about what we wanted to build together and how. In addition to being great consultants and building a great company that modeled our values, I wanted to explore ways of working outside of consulting, as I was feeling like we were reaching the ceiling of the impact that consulting could have. But, in theory at least, I was happy for that to be a stage two project, focusing our initial energies on building a great consultancy.

Over the course of several months, we converged on three priorities for our first year, the third of which was, “Space for Renewal, Learning, and Play.” Everyone was fully committed and aligned around this goal, and we did some things well. We did a good job of protecting other people’s time. We instituted practices such as starting all of our meetings with checkins, a tiny, but much needed pause that enabled us to breathe and be human together on a regular basis. We started tracking our time, which we all hated, but which gave us real data to see how we were doing collectively and to make adjustments accordingly. I designated my Wednesdays as "play days," which at minimum meant no meetings and at maximum meant open time to read, experiment, or simply take a break.

Unfortunately, I was still falling back on a lot of terrible habits. Running a company is stressful. A lot of people are depending on you to bring in revenue and to create a healthy, thriving work environment. I also felt urgency to do more. On top of the day-to-day challenges of building a successful consultancy, I was anxious to at least start exploring models outside of consulting, even though we had agreed not to prioritize this that first year.

All of this pressure — some real, some self-imposed — kickstarted my superhero complex. It was important to me that everyone else on the team had balance in their lives, but I believed that I could make do without, at least temporarily. I was motivated, I was confident in my endurance, and I felt it would move all of us forward without harming anyone. Besides, it would only be for a little while. Once we got over the hump, I could focus on restoring balance for myself.

Of course, it didn't work out this way. As a leader, I was not modeling the behaviors I was professing to prioritize. Everyone noticed this, everyone felt stressed by this, and — fortunately for me — everyone called me out on this. Moreover, intense stress and not enough rest was making me a bad teammate. It also was impacting my health. I thought I felt okay, but I discovered at a regular checkup that my blood pressure was alarmingly high.

This was the ultimate wakeup call for me. I needed to prioritize balance immediately. My life literally depended on it.

Turning the Corner

Shortly after founding my company, I started tracking a set of self-care practices every week on a dashboard that all of my peers could see. It was stark to see how often I neglected all of my self-care practices, including the low-hanging fruit, such as going for a walk. The simple act of tracking helped me make sure I was always doing some form of self-care, which was an important start.

However, it also made me see that "some" self-care was not going to be enough. This forced me to explore more deeply why I wasn’t able to make time to take better care of myself. I realized that working made me feel powerful and in control. When I felt like things were going poorly in my personal life, I defaulted to working as a way of feeling better about myself. I needed to confront these patterns head-on. I also adopted some simple tactics that helped. In particular, I took up photography as a hobby, which served as a much-needed creative outlet, helped reconnect me to my community, and unexpectedly had a profound impact professionally.

All of this core work turned out to be critical for me to implement the simplest and hardest solution of them all. In order to work less, I needed to stop doing something. That meant taking something off my list, which I had never managed to do.

I decided to leave the company I had co-founded, which — to this day — remains the hardest professional decision I have ever made. Leaving helped a lot. I was able to maintain a modicum of balance for the next few years, but I noticed that I easily fell back into old habits. I re-focused on working less, even declaring my intentions here on this blog. Repetition helped, and I was finally getting the hang of being real with myself and taking things off my plate. But, as it turned out, I needed to do one more thing before I truly turned a corner. I needed to stop checking my email so often.

Turning off my work email before dinner and on weekends had long been on my list of self-care practices. They were the easiest to do, and yet, after three years of tracking, they were the things I practiced the least. All of my hard work finally made it possible for me to do these “simple” things, and my self-care scores soared as a result. More importantly, it felt good. It turns out my email behavior was a good leading indicator of how much balance I had and also a keystone habit that unlocked other important practices.

In September 2016, I went to my self-care dashboard — as I had been doing every week for over four years — and decided that I didn't need to track anymore. After six long years of failing over and over again, I felt like I had finally achieved the balance I was seeking.

The following year, my nephew and his little brother came to visit me in San Francisco for the first time since that crazy week in 2009. I cleared my schedule so that I could maximize my time with them. We played basketball every morning, we went on long walks, and we ate delicious food. As I drove them to the airport at the end of their trip, I started to cry, not just because they were leaving, but because I remembered what my life and work was like the first time my nephew had visited eight years earlier, and I felt grateful for how my life had changed since.

Takeaways

It's been five years since I stopped tracking my self-care practices, and I've maintained this balance since. Not only am I as happy, healthy, and fulfilled as I've ever been, I am a significantly better collaboration practitioner than I ever was. Just as my bodybuilder friend explained with weightlifting, to get better at my work, I “simply” had to learn how to do less.

I share these stories not because I've landed on some magic formula for achieving self-care and work-life balance. Everyone's story and circumstances are unique, and I don't want to pretend that what worked for me will work for everyone. I share these stories, because I want folks to know that self-care is really, really hard. If you don’t already have work-life balance, there are likely very real, very hard reasons for this — both internal and external.

Achieving balance requires hard work, experimentation, and tons of support, and — if your experiences are anything like mine — you will fail over and over again. Even if you manage to achieve balance, you will always have to work to maintain it. You will constantly face obstacles, and old habits and mindsets will continue to rear their ugly heads. At the same time, achieving balance will also strengthen your faith in the importance and power of going slow, which will serve as motivation for you to continue your practices.

This matters, especially for collaboration practitioners trying to improve the performance of their groups. Working with urgency is not the same as working urgently. In order to be agile and impactful, in order to learn as you go, in order to do values-aligned work, pausing regularly isn't nice, it's necessary. One of the most powerful acts of leadership — regardless of your job title — is to model this. It's hard, but it may end up being the most important and impactful work that you do.

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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:

Admit you are a collaboration practitioner.
Breathe.
Start with you.
Listen and understand others.
Be intentional, and hold it lightly.
Stretch, but don't hurt yourself.
Be compassionate.
Do the work.
Pick yourself up.
Celebrate!
Reflect and integrate.
Share!
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:

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)

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)

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?