strategy – Faster Than 20

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

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

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

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

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

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

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

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

and this was my artistic rendition:

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

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

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

My 2020

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

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

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

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

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

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

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

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

Looking Forward and Backward and Forward Again

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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.

Why I Do What I Do, and What That Means for 2017

Seven years ago, a friend challenged me to clearly articulate why I do what I do. She had repeatedly heard my spiel — adopted wholesale from my mentor — about society’s problems growing more complex faster than our ability to address them and the resulting urgency to get collectively smarter faster. She understood what I was saying, but as far as she was concerned, it didn’t fully explain why I was so passionately driven by this work.

I spent many months reflecting on her question, repeatedly asking myself why, and challenging myself to go deeper. The answer finally came to me in L.A., where I was visiting my parents and younger sister. We had gone to the beach together, a family tradition since childhood, and when we arrived, as if on cue, my family immediately splintered. Everyone moved in his and her own direction, with no sense of what anyone else was doing and no coherent rhythm. I watched this lack of synchronicity unfold before me and felt all sorts of old wounds rise up within me.

I was lucky to grow up in a family with lots of love, but — like all families — we had our share of dysfunction. Some of that dysfunction felt especially jarring, considering my parents’ strongly-held value of togetherness and mutual support. As a kid, I grew frustrated over watching seemingly little things disrupt our ability to be together, especially lack of listening, communication, and self-care.

I also had the good fortune of experiencing really great collaboration with others, starting with my love for team sports. I have always been a mediocre or worse athlete, but I quickly learned that teams that practiced together and that played with heart and smarts could easily transcend any individual shortcomings, and I grew to love how it felt to do that. In other collaborative pursuits where I already individually excelled, I found that I could channel my strengths into lifting others, which led to greater success than what was possible by myself and which felt even more joyful and satisfying.

I knew what it felt like to move together in sync and with power with others, and I wanted it in all aspects of my life. I knew that the fundamentals of this wholeness were simple, but not easy, and that small, but significant gains were easily within reach for most groups. When I met and started working with my mentor in 2000, all of this came together for me. I had discovered my purpose and my passion, and I was ready to make it my life pursuit.

2016 Lessons Learned

2016 was a hard year for me on two fronts. I had spent the prior three years experimenting with this notion that the key to high-performance collaboration was practice, and I had directed all of my energies toward exploring ways to encourage and support practice at scale. I wanted to spend this past year focusing on the things I had learned that felt the most promising. My goals were to:

Scale up my Collaboration Muscles & Mindsets program and Do-It-Yourself Strategy / Culture toolkits, while continuing to refine and improve them
Continue to find ways to support emerging practitioners, including finding ways to connect them with each other and offering real opportunities to practice with me and each other
Return to my consulting past by taking on a really big, really hard problem, incorporating the things I had learned over the past three years, while also telling the story of the work as it happened, so that others could learn from our successes and failures in real-time

While I did plenty of work I felt proud of, most of the things I tried did not work out the way I had hoped. More egregiously, I felt like I ended up making excuses that prevented me from trying things that were higher-risk, higher-reward. Specifically:

In general, I was not disciplined about writing up and sharing what I was learning in the moment, which resulted in only two blog posts in 2016, compared to seven in 2015 and 30 in 2014! I published more posts in this blog’s debut in December 2013 (five) than I did in all of 2016.
This lack of storytelling was particularly bad with my really big, really hard client project. We did good work together, and we also struggled at times. While we did the work transparently (including creating a public dashboard, synthesizing and sharing our framework for experimentation, modeling transparency internally, and inviting outside colleagues to shadow), we did not share enough context for what we were doing for others to be able to learn with us. Some of this was beyond our control, but there were other things that were simply failures on my part, including not writing a single blog post about the project.
While I did some work toward refining and scaling up Collaboration Muscles & Mindsets and the DIY Strategy / Culture toolkits, most of it was reactive rather than proactive, and even then, I was very slow to react. I ended up missing lots of simple opportunities to spread the word and involve other people. For example, Duende, my design partner for the toolkits, created an online store where you can order the toolkits, but you can’t find that store from my website. (Voila! The preceding sentence fixed that problem! More to come!)

While I didn’t accomplish my high-level goals, I don’t want to lose sight of the good things that happened:

Publishing blog posts is not the only thing that matters when it comes to sharing. It’s about the quality of what you share and the number and kinds of people you reach, regardless of medium. I found myself sharing and linking to my two 2016 blog posts more often than average. While I only wrote two, my colleague, Anya Kandel, became the first guest contributor here, writing two really great blog posts about her driving questions and experiences.
In addition to writing up the aforementioned experimentation framework (which I did in collaboration with my colleague, Alison Lin), we did an accompanying webinar in partnership with Social Transformation Project and Leadership Learning Community (LLC) that had almost 400 registrants, third all-time among LLC’s excellent five-year roster of webinars.
I published several of my collaboration workouts, with more to come. My lack of blog posts didn’t prevent my mailing list from growing, and you can now follow me on Instagram and Facebook as well as Twitter. I also made a bunch of subtle design and technical changes to this website, which will help support its ongoing growth and evolution.
I did a Do-It-Together Strategy / Culture Workshop in New York with Anya Kandel, my first outside of the San Francisco Bay Area and hopefully the start of many more.
I maintained the self-care success that I achieved in 2015, not a small feat considering how much work I’ve put into this over the past four years.
I met, worked with, and shadowed lots of great practitioners, especially the aforementioned Alison and Anya, through my informal meetups, my colearning experiment and a similar experiment with my friends at MAG, and my client work.
My client projects were meaningful, and I learned a ton from each of them. I did organizational culture work with Addapp, organizational strategy work with General Service Foundation, which included a strategy-focused Muscles & Mindsets program, and really meaningful work on network strategy and culture with Social Transformation Project, my heretofore un-blogged-about “big, hairy client project.” I got lots of practice, including designing and facilitating two unusually challenging meetings, and I identified lots of areas for ongoing improvement. In addition to having lots of new fodder to write about, I also developed lots of new infrastructure and templates that I plan on packaging and sharing this year.

It’s not that I didn’t accomplish good, valuable things. It’s that I have a larger goal that I care about, and the only way I’m going to have a chance at achieving that goal is through focus, discipline, and rapid adaptation. I’m trying to run a marathon, and while I worked hard and am in better shape now than I was a year ago, I’m not developing strength and endurance quickly enough to successfully complete that marathon.

Which brings me to the second thing that was hard about 2016, for me and for many, many other people.

There are many, many problems in the world today, and they all manifested in some very discouraging ways this past year. All of this divisiveness, siloization, and radicalization are what I and many, many others have been working so hard to shift and prevent for many, many years. These are fundamentally challenging problems, so it shouldn’t come as a surprise that it’s happening, but we can’t use that as an excuse not to be disciplined and accountable to how we’re trying to tackle these problems.

How do we know if we’re investing in the right places? Where should I be directing my energy in order to have the biggest impact?

I don’t know the answers to these questions. I do have hypotheses, and my intention has been to test them. My actions in 2016 were not fully aligned with my intentions, and I want to fix that. Which leads me to my three-year goal and my priorities for 2017.

1,000 High-Performing Collaboration Practitioners by 2020

I believe there are a set of core principles underlying high-performance, collaborative work. I believe we need lots and lots of people who understand those principles and who practice them with devotion and joy.

I practice these principles to the best of my ability, and I want to find others committed to the same principles, whether they are external practitioners trying to help other groups or internal changemakers embedded in their own groups. I want to learn with them, support them in their practice, and help the community grow and improve. By the end of 2020, I want to know of at least 1,000 of these practitioners all in movement together.

Why 1,000? Because I think that number is the minimum needed to sustain a thriving, growing movement.

Why by 2020? Because I think it will be very hard, but doable if I’m smart and focused about how I approach this, and because we can’t afford to wait any longer.

How will I accomplish this? I’m still working out the details, but I’ve got some ideas. I think there are three overlapping categories of activities needed to help catalyze this community of practitioners:

Model these principles myself and continue to practice and improve
Synthesize and share what I’m learning
Nurture and support other practitioners

Most of my past activities have fallen in some subset of these categories, as is the case for similar practitioners. But I’ve realized (through experience and lots of helpful feedback from others) that there are some key activities on which many of these other activities depend. I’ve largely neglected these activities, and I want to correct that.

2017 Priority: Draft a Set of Experience-Based Principles for High-Performance Collaboration

In particular, I need to clearly and accessibly articulate the principles that I think are foundational for high-performance collaboration. Drawing on my and other’s experiences to draft these principles will be my primary focus in 2017.

I often use the metaphor of how we need more chefs. In some ways, I’m saying I want there to be 1,000 “chefs” that I know of by 2020. We can extend this analogy further to explore how we might go about doing this.

One of the reasons I decided to start consulting again at the end of 2015 was my realization that we need more “great restaurants” in order to inspire people to become “chefs.” I thought one of the highest-leverage things I could do was to be one of those restaurants. I wanted to scale up how I modeled the principles of high-performance collaboration in order to inspire others to push their own practice.

I still think we need more “great restaurants,” but I no longer think that’s where my focus should lie. I need to be clear about what I think high-performance collaboration means and what the underlying principles are. Articulating those principles will help serve as a beacon for other practitioners with similar beliefs and commitment. It will provide a framework to help assess collaborative performance — the equivalent to a Michelin Guide in the restaurant world — which is an important step toward actual improvement.

I hope to have a first draft of these principles — which I’ll pull together in an open way with the help of my community (which I hope includes anyone reading this) — by the middle of the year, at which point I’ll use it as a way of scaling up my other activities. I will continue to model and practice, but it will all be in service of articulating these principles.

I’m excited about this renewed focus. It feels true to the reason I got into this business in the first place. I know what high-performance collaboration feels like, and I’ve learned a lot about helping others achieve it. I know that others know a lot as well, and that even more people want to know and learn. I think the path for supporting these practitioners — lots and lots and lots of practice — is straightforward, but challenging, and I’m excited about re-focusing my efforts to pave this path. I believe wholeheartedly in the world that is possible if we’re successful, and I’m going to do everything I can to help create that world.

Do-It-Yourself Strategy and Culture

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:

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.

Working Less (and Other 2015 Strategic Priorities)

For over a decade, my work has fundamentally been about creating a world that is more alive. My specific focus has been on building up society’s collaborative literacy — the muscles and mindsets we need to be and work together more effectively.

Every year for the past five years, I’ve carefully mapped out a set of goals and strategies that I think will put me on the best path toward realizing my vision. In each of those years, I’ve had three priorities, and the third priority has always been something around work-life balance. In each of those years, I’ve monitored my progress and made adjustments throughout, and at the end of each year, I’ve assessed my overall progress.

Every year for the past five years, I’ve seen a similar pattern. I do well on all of my goals except for the one on work-life balance. I’ve seen incremental improvement every year, but I continue to be far from my targets.

I spent a lot of time at the end of last year reflecting on this. Was this the right goal? Did I need to reframe what I meant by work-life balance? Or did I simply need to experiment with different strategies?

I decided that it was still a critical priority for both personal and professional reasons. I believe in the importance of slowing down, that balance and pace will make me a better practitioner and a better person. I believe that we as a society need to be better at this, and I want to model this practice.

So I kept it as a goal, but I made a few changes. I reframed it slightly, and I made it my top priority.

This year, my number one strategic priority is to work less.

Working less is a clear goal. I’m confident that my metrics (which are based on hours worked and some self-care indicators) are relevant, and I’ve got specific targets, which means that I can clearly and objectively see whether or not I’m achieving this goal. If I hit my targets, I’m confident that I will be happy and healthy.

The real question is whether or not working less will make me more effective at achieving my higher-level goals. I believe it will. If I’m forced to work less, that means I’ll also have to work smarter. I’ll have to make better decisions about how I use my time, which means saying no more often than saying yes. I believe I already have the muscles to do this. Constraints will give me the incentive to use these muscles.

Three months into 2015, I’m thrilled by the results so far. I feel like I have plenty of space to think about the big-picture and also to focus and get things done. I’m seeing the people I want to see, and I’m deepening my relationships and my practice. I’ve definitely had to take things off of my task list — it’s no accident that this is my first post here this year — but the tradeoffs have been worth it, and I think my focus will pay off in big ways.

To understand what this means more concretely, it’s important to understand my other two strategic priorities for 2015. First, I’m focused on building a platform for developing collaborative literacy. Second, I’m looking to engage with 1,000 changemakers.

Building a Platform

I believe that the best way to develop collaborative literacy is through lots and lots of practice.

I’m supporting practice in two ways. First, for the past two years, I’ve been developing and prototyping workouts under the auspices of my 15-week Collaboration Muscles & Mindsets program. I’m really excited about how the program has evolved, and I’m looking to document and distribute what I’ve learned more widely (and, of course, freely). I’m currently doing the program with Forward Together and some of its partners as part of a larger innovation process, and I’m looking for others who’d like to try it. (Contact me if you’re interested!)

Second, I’m trying to create the equivalent of balance bikes for changemakers. These have largely taken the form of DIY toolkits for developing strategy and culture, which I’ve been developing in partnership with Duende and many others and which will also be freely available.

I’ve been prototyping these with lots of groups over the past year, and I’m super excited by how effective they’ve been. Several practitioners have already incorporated these toolkits into their work, and demand has been high. I’m focused on continuing to refine and improve these toolkits and also documenting and distributing them in order to meet demand.

I care about chefs, not recipes, so I’ve been consciously focused on developing tools that support practice rather than writing things that are prescriptive. A number of colleagues have pushed back, suggesting that I’ve been too extreme about this. They’re right. Even though my frameworks are extremely simple, I still have them and ought to share them more proactively. I’ve written about some of them here, but they’re not easily findable. Part of the work of building a platform is weaving these frameworks together so that they’re widely accessible.

Engage with 1,000 Changemakers

Toward the end of last year, I sifted through lots of data to try to get a sense of how many people I engaged with. I came up with roughly 250. A surprising number of those were face-to-face or phone interactions, so 250 felt like a lot. But if my goal is to scale practices that will improve collaborative literacy, I need to reach a lot more than 250 people.

To some extent, creating a good platform — for example, simply documenting and publishing my aforementioned toolkits — will help expand my reach. However, simply hitting my numbers are not the point. The quality of engagement matters, which means going beyond simply making my work more accessible online.

Specifically, I’m focused on deepening my engagement with a core set of practitioners. I’ve been doing that with a small, local group of peers, which we call our “colearning group.” I’ve also been much more intentional about finding and working with emerging practitioners. All of this has helped my own practice tremendously and has also led to better toolkits.

It’s also been the best way to disseminate practices and mindsets for doing this work effectively. Every one of these practitioners are already taking what they learn out into their own communities, and a better platform will better support them in doing so. Furthermore, by modeling a culture of shadowing and mentorship, we are hopefully encouraging others to adopt similar learning practices.

This year, I hope to write less frequently, but more impactfully. I’m excited by what I’ve been doing and learning so far, and I’m looking forward to sharing more in the ensuing months.