Do-It-Yourself Strategy and Culture

Biker

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

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

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

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

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

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

And that’s essentially what we did.

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

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

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

Breakfast and Culture

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

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

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

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

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

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

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

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

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

DIY Strategy and Culture

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

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

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

Strategy / Culture Questions

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

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

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

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

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

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

Working Less (and Other 2015 Strategic Priorities)

Child Labor

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.