Dharmishta Rood – Faster Than 20

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.

The Key to Effective Learning? Soap Bubbles!

Part three of a three-part essay on facilitating group learning. See parts one, “Getting real about experiments and learning,” and two, “Documenting is not learning.”

Two months ago, I blogged about my experiment with Dharmishta Rood and the Code for America Incubator, which wraps up in another few months. The goal is to help startups — in this case, a company called PostCode — develop great collaborative habits in its formative stage. The theory is that it’s more effective to build good habits from the start than it is to try to change bad habits later.

About a third of the way into our experiment, Dharmishta and I started discussing whether or not we thought it was working. We thought that it was, but we weren’t sure whether or not the folks at PostCode would agree. “We’re missing soap bubbles,” Dharmishta asserted.

“Huh?!” I responded.

Soap, Dharmishta explained, does not naturally produce bubbles. Manufacturers add chemicals to make soap lather, even though the resulting bubbles have no impact on cleanliness. In fact, some chemicals have adverse effects, such as drying out skin.

Why do they do this? Because people associate bubbles with cleanliness. If we don’t see the bubbles, we assume it’s not working, regardless of whether or not that’s the case.

When assessing progress, how you feel matters.

If you’re learning, and you feel like you’re learning, then all is good.
If you’re learning, but you’re not feeling like you’re learning, then you have a problem. You may stop doing things that are working, because you don’t realize that they’re actually effective. This is where adding soap bubbles can be useful.
If you’re not learning, but you feel like you’re learning, then you also have a problem. There is where adding soap bubbles can be harmful.

Given this, how do you design soap bubbles into your learning processes that help, rather than harm you?

It starts by being real about what you can and can’t measure, and it quickly shifts to remembering what you’re trying to achieve in the first place. There is always an intention underlying our instinct to measure, but sometimes, the complexity around measurement causes us to forget that intention.

I’m generally trying to help groups learn how to collaborate more effectively. I want feedback mechanisms that reinforce good habits and discourage bad ones. In PostCode’s case, Dharmishta and I wanted to make sure that the team was communicating and making decisions effectively. We thought that we were seeing progress, but we weren’t sure that the team was seeing the same things we were. We were (and still are) worried that the team would discard the practices before they became habit.

We designed a monthly “assessment” to help PostCode track its progress, and when we started exploring ways to measure effectiveness around communication and decision-making, we decided to take a different approach. Rather than attempting to quantify those things (as we were doing with the other dimensions we were tracking), we decided to ask qualitative questions:

Please share up to three examples of great, effective communication over the past month.
Please share up to three examples where communication could have been better over the past month.

(We asked the same questions about decision-making.) These questions will not provide some “objective” measure of how well the company is communicating as a whole or whether or not it is improving over time. However, they will:

Encourage everybody to regularly pause and reflect
Surface people’s different perceptions of what is good and what is not
Identify problems that need fixing while they’re still fresh
Remind people to celebrate what’s going well

Most importantly, these questions will remind everybody that communication matters, and that they should be practicing consciously and with an eye to improve. The very act of pausing to answer these questions on a monthly basis means that they are. These questions act as soap bubbles, but they also help clean!

Measurement is important, but feedback is even moreso. Figuring out the right things to measure is hard, but creating feedback mechanisms is not. Soap bubbles may not give you objective indicators for tracking progress, but they will — at minimum — remind people of what they’re trying to accomplish and to be conscious of when it’s happening.

Photo by Umberto Salvagnin. CC BY 2.0.

Organizational Development as Product Design

I got my start in the tech industry. Even though that was a lifetime ago, I’ve carried over many lessons from that experience, and I like to keep one foot in that door. One lens I still carry with me is that of product design.

I’m currently embarking on an experiment with Dharmishta Rood, who runs the incubator at Code for America. The gist of the experiment is this: Changing organizational habits is hard. Starting new habits is easy. If you want to build a high-performance, collaborative organization, the best thing you can do is instill good habits right from the start. Incubators are in a great position to do just that.

Code for America is trying to help local government truly live up to its promise of for the people, by the people. Its central activity is a fellowship program that connects designers and developers with local governments for a year. Think Teach for America for geeks. On the surface, these fellows design innovative applications for local government. On a deeper level, these fellows help change the culture of local government. It’s an amazing organization, and I’ve been a proud supporter for many years now.

Sometimes, fellows want to continue working on their apps beyond the fellowship. Last year, Code for America started an incubator program to help their fellows do just that. One of the many things that Dharmishta does is find mentors and trainings to improve her startups’ chances at success. One of the services she wanted to provide for her current class — a great new startup called PostCode — was help with getting better at collaboration.

I’m looking for ways to scale collaborative literacy. Helping an incubator instill great collaborative habits with civic startups seemed like a wonderful opportunity to do exactly that. The twist was that I didn’t want to do the work. I know how to do that already, and I know that I’m not scalable. Instead, I wanted to see if I could create a toolkit that Dharmishta could implement on her own with some behind-the-scenes coaching on my part. Dharmishta and PostCode both graciously agreed to try this experiment with me.

This is essentially a product design challenge, and it’s been incredibly humbling. We whipped together a prototype in just a few weeks, but I based it on years of experience, and I thought it would be great. It’s been solid so far, but not great. Watching Dharmishta and PostCode work through the toolkit behind-the-scenes has been an exercise in frustration — not with them, but with my own work. It’s uncovered all sorts of flaws and faulty assumptions, and because I’m not the one implementing it, I can’t make adjustments on the fly, which I do regularly in my own practice. It’s providing value, but it’s not living up to my expectations.

Which is exactly the point. Unless you’re incredibly lucky, you’re not going to get it right on the first try. Good product design is about getting your best first guess out there as quickly as possible and learning as quickly as possible based on real world usage. You take your lumps early so that you have a better chance of getting to the right answer quickly (and cheaply).

I wrote in an earlier post:

In order to design an effective tool, [product designers] use powerful methods for understanding how their customers think and feel and for measuring the impact of their interventions. Most process designers would do well to learn the tools of product design.

Most process designers I know have a very limited toolkit. They are typically over-dependent on meetings to accomplish their goals. (The exception to this are folks I know in tech startups, who tend to have more of a — you guessed it — product mindset when developing their own organizations.)

The bigger problem is that most process designers do not spend enough time up-front thinking about how to measure success. This ends up being fine, because most don’t bother to assess their work afterward anyway, outside of a casual, gut-feel conversation with a very narrow set of people.

I can say all of these things without judgement, because I have been guilty of all of these things. Doing these things well requires a tremendous amount of discipline, practice, and boldness. Frankly, I don’t know many product designers who do all these things well either. But on average, I find that product designers have a very different mindset than process designers.

What exactly is this mindset? That you don’t know all the answers. That underneath your considerable experience lies a foundation of faulty assumptions. That the way to learn is to move forward constantly, but thoughtfully, to iterate rapidly, to assess obsessively, and to assume that you will fail many times before you succeed.

This is the approach that I’ve been taking with the “product” that Code for America and PostCode has been using. They are both tremendously busy, but they have been great about playing with the toolkit. PostCode is a company full of product designers, and that mindset is strongly engrained in Code for America’s culture as well. (Code for America is an ardent evangelist and practitioner of the Lean approach, whose chief evangelist, Eric Ries, serves on its board.) They understand the spirit of what I’m trying to do, which has helped me a lot in doing this experiment.

This shared understanding has also helped me explain some principles of organizational development with them. PostCode is grappling with the typical startup challenges — lots of opportunities, but also lots of uncertainty, the need to focus in light of this uncertainty, and the challenges of norming as a team in the midst of the thousands of other things they need to be doing. They need to go fast, but they also recognize the importance of slowing down.

We were discussing the challenges of deciding on decision-making processes, and I latched onto something very wise that one of them said: Sometimes, things will actually work themselves out if you just let them play out. You want to be thoughtful and reflective, but you can’t let that paralyze you. The value of actually trying something, then stopping to reflect, is that now you’re basing your decisions on real data rather than on a bunch of competing, subjective, abstract notions. That’s a product designer’s mindset, and organizational development practitioners would do well to adopt it.

The trick is finding the balance between doing the work and taking a step back, doing the work and taking a step back. That’s what I’m trying to help them do. It’s an incredibly hard balance to learn how to strike. Clients have been hiring me to help them with this for years, yet I found it extremely difficult to do myself when starting up my own company a few years ago. I continue to improve, but I’m still in that cycle of trying and learning.