How a designer builds a startup
When I joined Google in 2007, everybody said, “If you want to learn how to get things done, watch Braden Kowitz.” Braden was a designer who’d worked on the first versions of Google Sheets, Google Trends, and Google for Business (which is now G Suite).
Over the years, I learned a ton from watching Braden. I got to work with him for a few years, first on Gmail, then later at Google Ventures, where we also collaborated on a book. He was and is an excellent leader, but maybe what is most impressive is what an excellent learner he is—curious about every facet of product development, from research to engineering to marketing, and, of course, design.
Now Braden is a startup founder. His company, Range, is building software for teamwork. It’s a system of tools for connecting smaller dots (daily check-ins and meetings) with the big picture (larger team goals and OKRs).
Because he’s such a great learner, I thought it would be super interesting to look inside his process. I asked Braden if I could interview him about what it’s like for a designer to build a startup—and how it feels right now, when his company is at a crucial moment on their quest for product/market fit.
Here’s our conversation:
JAKE: You left Google Ventures, where you spent years coaching startups, and founded a startup of your own. What that was like?
BRADEN: It’s challenging in a good way. Startups push you hard to grow, which is a double-edged sword.
On the one hand, it’s amazing to grow so fast. I’ve had to learn about marketing, sales, team culture, legal contracts, and much more. I’m grateful I’ve taken this path of founding a startup.
But growth is often uncomfortable. It’s impossible to be good at everything. And at a small company, a few people really do need to do everything. Startups constantly highlight your own ignorance and incompetence. No matter how fast you learn, there’s always going to be more that you could be doing. That’s hard. And it’s easy to let all that pressure crush you.
JAKE: Jeez… so how do you keep the pressure from crushing you?
BRADEN: I’m reading Dune right now. Yes, I know I’m a nerd. But there’s this great quote:
“I must not fear. Fear is the mind-killer. Fear is the little-death that brings total obliteration. I will face my fear. I will permit it to pass over me and through me. And when it has gone past I will turn the inner eye to see its path. Where the fear has gone there will be nothing. Only I will remain.”
So beautiful. And good in theory. But how do you let fear pass over you so that you can continue to grow?
The book An Everyone Culture covers a great framework for building this kind of culture where teams are pushed hard and grow fast. It suggests building a Home, where people feel safe and supported. Then building a Groove, where people feel rhythm, momentum, and progress. And finally, with that foundation, building an Edge which pushes your team to grow.
You’ll frequently hear startups described as a rollercoaster ride. There’s no escaping the Edge. So I’ve learned the importance of building a Home and a Groove for our team (and for myself). It’s those two foundations that allow our team to weather the ups and downs of the startup journey.
JAKE: You’ve designed lots of products, but now you’re a one-person design team AND a co-founder. Tell me about designing Range from scratch.
BRADEN: For the first month, I didn’t design anything. I just talked with potential customers. Our mission is to help teams work better together and help organizations scale effectively. So there were plenty of topics to cover. After a few dozen interviews, I poured through the transcripts looking for patterns.
It became clear that many teams struggle to stay connected as they grow. And that feeling of disconnection expresses itself in a few big ways. Managers want to know what’s happening, but feel disconnected from the daily work. At the same time, individual contributors struggle to connect their work to larger goals. And culturally, it’s hard to feel connected as a team when many new people are joining, or when everyone is working across several locations.
You should always pick a design methodology that’s well matched to the problem at hand. And this problem is crazy complex. So we used an extremely iterative approach. We built small features, gave them to teams, listened to their feedback, and improved the product step by step. We still use critique and user studies. But for software that’s used by groups of people, it’s very difficult to predict outcomes. It’s much more effective to build, ship, learn, and iterate.
JAKE: That’s pretty interesting, because for most design problems there is some kind of reference already out there. It sounds like what you’re building at Range is new and unique enough that you really have to invent the thing?
BRADEN: Yes, as designers, when we approach a problem that’s been solved before, it’s usually fairly easy. You can dip into a large well-known pattern library, and assemble an experience that will probably work. Of course, it never does work on the first try, but with a few rounds of user research you can get really close.
But when you’re attempting to design software that improves how people work together, things get way harder. You’re not designing for a single persona, but several different personas at the same time. And the features you design interact in unexpected ways across a social group.
JAKE: How different is the product today from where you started?
BRADEN: Range feels completely different every six months or so, even though we’ve never done a redesign. We simply work iteratively.
At first, Range was just daily check-ins that helped teams stay in sync. Then we realized that check-ins would be a lot easier if you could import work from other tools, so we started adding integrations. Of course, many people don’t work on just one team, so we built multi-team support. Then we took even bigger steps and started helping teams track goals and run better meetings.
As we added more to Range, we were careful to pay down design debt as we went. Just this week I noticed that we had 3 different icons for meetings. That’s an easy fix. But at other times, we realized that Range was getting hard to navigate, so we’d work on information architecture for a couple weeks.
JAKE: But isn’t that a redesign?
BRADEN: No. Navigation is just one part of the product. I’ve never been a big fan of large product redesigns. While it feels great to wipe the slate clean and design from first principles, redesign projects are extremely risky because you’re changing so much at once.
Our process at Range has been to encourage free thinking, but then to build iteratively. I often sketch redesigns, but then we scope down ideas to the next small thing we can build. Inevitably, we learn something on the journey that shapes our vision of where we want to go next.
Building software is a lot like the “Ship of Theseus” thought experiment: A ship leaves a harbor, and during the journey, sailors slowly replace every part on the ship. Is it the same ship when it returns? No, hopefully it’s better. Because in the case of a startup, you leave the harbor with a dinghy and hope to return with a cruise liner.
JAKE: What kind of boat is the Range product at this point, on the dinghy-to-cruise-liner continuum?
BRADEN: A 40-ft sailboat. It can weather most storms and runs on very little fuel.
JAKE: Okay, so what’s the next challenge for Range? How do you take your sailboat to product/market fit and the revenue you need to keep the company going?
BRADEN: We’re at the point where we have confidence we’ve built a solid product. So our next big challenge is marketing and sales. We already have a great customer base, with companies like Twitter, Coursera, and WeWork. But investors need to know that Range can continue to grow by finding new customers, telling a compelling story, and delivering a valuable product. We do all of that already. Now it’s about finding ways to scale those processes.
In product design we sketch many solutions, test them with customers, and find what works. The market side is very much the same. But instead of designing product, you’re designing the market approach. You’re testing many different ways to reach customers. You’re trying different ways of describing the customer’s pain and how your product can help. And hopefully after a lot of experimenting, you discover a couple of scalable channels to grow your business.
JAKE: What’s your advice for designers who want to found a startup?
BRADEN: The biggest advice I have for designers considering founding a startup is to see everything as a design problem. There’s so much to figure out in the early days, that you’re probably not going to be focused on product design more than 2–3 days a week.
You’ll be focused on the rest of your business, where there are difficult challenges that feel way outside of your area of expertise. Just remember that you can apply your design toolkit to all sorts of challenges. And there will be giant existential challenges. Just approach them like any other design challenge: gather data, understand what’s happening, brainstorm things to try, select the best options, and then keep building and learning. Eventually you’ll find your way through.