Startup Habits Workshop at Code for America

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.

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