Design Leadership & Culture at thoughtbot

Andrew Cohen

Over the last few years we’ve witnessed the maturation of the designer role. Companies are investing in designers beyond just pushing pixels and production work. People rely on designers more-and-more for business and product decisions. With this growth of opportunities we’ve seen more designers taking on leadership roles and fostering design-centric company cultures.

At thoughtbot, we’ve always emphasized and understood the importance of design in product development. We were one of the first consultancies to employ product design sprints created by Google Ventures. Our team has released numerous open source tools for designers in the form of bourbon, neat, and bitters. Internally we’ve been improving the design culture through research and a slew of experiments. However, we didn’t have a single designer in a management position within the company.

Design has its seat at the table. Our leadership team felt that if the design culture was to continue growing we needed to have designers in management roles. So, last year we introduced our first Chief Design Officer and the Design Director role.

To keep with thoughtbot’s flat organizational structure, we didn’t want to add additional levels of hierarchy. Instead of creating a middle-management layer, we view Design Directors as a support layer for our co-workers. We needed them to continue growing the internal design culture while ensuring the success of their team.

So what does a Design Director do?

Traditionally, design management roles have been more inline with Art Directors inside ad agencies. The Art Director role conjures up images of hovering people telling you to nudge it 10 pixels to the left. Micro-management is very anti-thoughtbot, and unpleasant in general.

Instead of going the traditional route we’ve been using this opportunity to continue building the design culture in each of our respective offices and throughout the company. Design Directors are still actively working as designers on their own projects, alongside the rest of the team. On top of that, they are making sure their team is happy, inspired, and successfully delivering for their clients. They facilitate critiques, discussion of new processes, exercises, outings, help with sales leads, and any problems whether code or client. We also look to push forward any ideas or concerns our local team has outwards to the entire company.

The team in Denver specifically brainstormed and established a handful of things to help push our design culture further. We’ve found balancing the frequency of the following activities has helped grow our design culture without them becoming too much of a nuisance. After all, more meetings for the sake of it is never a good thing. While the team helped establish some of these activities, the Design Director is responsible for making sure they happen.

Design Critiques

Our team talks daily about our work. We’re constantly pairing and helping each other with problems that crop up. However, sometimes we get so wrapped up in our projects we never step back and get an outsider’s view. Weekly design critiques allow us to present our project, get the team’s feedback, and work through any of the tough problems we’re having. As a director, I find myself picking someone to present the day before, and facilitating a basic conversation around their work to keep us on track.

Designer’s Book Club

With the amount of articles, books, and topics to stay up-to-date with, one can easily get overwhelmed. Each of us wants to continue learning, but can often have a hard time staying motivated. By establishing a book club it holds each of us accountable to learning something new together.

Every other Friday we sit down to discuss a few chapters. Our conversation often ends up focusing on ways to improve our design process from what we’ve learned. I’m often the note-taker and frequently walk away with actionable items to help push changes and ideas further.

Design Exercises

The New York City office has been enjoying lunch-time draw time on Fridays for a while now. They found it was a great way to end the week, but also a chance to be creative away from the screen. We decided to bring that into the Denver office and expand on it.

We spend our entire week in front of our screens working on features and user flows. Beyond that, designers are easily susceptible to creative burnout. By being creative and practicing problem solving away from the screen we’re able to refresh ourselves.

Every other week I find an exercise we are going to work on. The team at Foursquare came up with a great list of exercises I often refer to.

Sounding Board

Directors are here as a support layer and want to help with any problem a designer might come up against. Whether it’s a design solution or a tough client, we’re here as a sounding board to help out. I never try to prescribe solutions to a problem and often draw on my past experiences to help guide other designers. However, I never outright state I would do it a certain way. By avoiding that it allows them to find a solution themselves. I’m here to get their brain churning and moving in the right direction.


By establishing design leaders within thoughtbot, we’re able to grow the design team and culture. Design leadership shouldn’t be about hovering over someone’s shoulder, or nitpicking their work to death. It’s about enabling our team members and ensuring they’re able to produce the best work possible.

Our directors have a slew of other tasks they handle. Inspiring, enabling, and helping their team learn should be at the top of their priorities. The activities above have helped establish ways for directors and team members to do that. They provide a way for each designer to learn, grow, and stay successful day-to-day. This is the right way to go about leading.