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Figures of Progress: Bobby Grace, Lead Designer at Trello

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Not too long ago, real-time project collaboration in the office meant that team members had to convene in conference rooms and brainstorm using whiteboards or notepads. Today, distance is no longer an obstacle to real-time collaboration, and cloud-based services like Trello are gaining popularity because they allow productivity and information exchange from anywhere. As lead designer at Fog Creek (the company that created Trello), Bobby Grace works to make sure the company’s cloud-based software maximizes efficiency and continues to rethink the human side of productivity, without complex bells and whistles to confuse or inhibit it.

“People have to deal with so much frustrating productivity software,” says Grace. “It tends to get complicated very quickly and ends up being more unpleasant than accommodating. So I hope Trello makes people realize software can be friendly and simple and still be useful.”

Trello organizes projects in the same intuitive way a person might organize index cards and file folders. Users can create checklists, color code shufflable cards, and share their project cards to an entire group. Collaborators can update and track projects together in real-time without being in the same room or exchanging long email chains.

Of course, just because a software product like Trello is intuitive and simple, doesn’t mean the journey to create it is. “Deciding on big, new features is a long, messy, painful process,” explains Grace. “Everyone has a voice and a chance to defend their ideas. It ends in a lot of stalemates. I think that’s a good thing, though, even though it’s not always fun. It keeps the software from getting bloated with features and it means that we’re all happy with what’s out there.”

There are literally endless ways they could upgrade the software, so Grace and his team gather data to help them make informed decisions for improvements. And surprisingly, unlike many companies, he doesn’t rely on quantifiable data like demographics to analyze users. “Demographic data is not all that useful. It might help us tailor a message to specific groups of people, but…[if] we make [the software] better, we try to do so in a way that makes it better for everyone.”

Instead, Grace opts for the equivalent of the old fashioned comment box. “Feedback is our most valuable data,” he says. “Feedback comes from support emails, Twitter, the Trello Development board, or talking to people. It’s all very anecdotal and subjective; not the easily crunchable, quantitative type of data.” And rather than using automated systems to collate and filter that data, a person on the team is charged with synthesizing the feedback information, combining it with previous learnings, and then sharing suggestions for solutions.

This human-focused side of data gathering and development is not new for Grace. “I took one computer science class in college, a C++ class. I hated it. It seemed so cold and inhumane,” he remembers. It wasn’t until he realized that coding data could help people that he felt inspired. “When I published something that anyone in the world could see—even if it was just data for Kansas reservoirs—it clicked for me.”

For the Fog Creek team, valuing the the human side of information has shaped Trello’s ability to fuel better collaboration between users and their own development process. “I do improv comedy in my free time,” says Grace. “You quickly learn that the group mind is more powerful than the individual. Getting everyone on the same page is 90% of the work.”

Read more from leaders like Grace at Figures of Progress, including interviews with Matthew Stinchcomb, VP at Etsy, Jennifer Pahlka, founder of Code for America; Adam Brotman, chief digital officer of Starbucks; Rachel Sterne, CIO of the city of New York; and Oliver Hurst-Hiller, CTO of

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