Working From Woods

Sam Goertler
Building Asana
Published in
4 min readAug 26, 2014

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An unconventional kick-off to Asana’s upcoming redesign

It was our last night in the woods and we were all sitting around the fire, silently gazing at the stars, appreciating nature. All of the sudden, our designer blurts out, “Modules! We should put task lists and team members inside modules on a project page!” Everyone’s eyes immediately lit up and we all listened intently as she put the pieces together for what would become Asana’s new UI.

You’re probably wondering why we were planning a website redesign late at night in the woods. Well, redesigns are often big, scary projects for PMs and this one’s no exception. Not only do we need to update our visual style, but we also need to rearrange some existing features and clean up navigation.

“The Before”- Asana’s website pre-redesign

So where did we begin? Like most projects at Asana, we kicked off with a brainstorming session.

We knew we couldn’t come up with the freshest ideas inside a conference room, so I suggested renting a cabin in the woods.

After talking to friends who led successful redesigns at other companies, we confirmed that a change of scenery would be a good way to free us from reminders of the current design and getting out of the office would help us minimize distractions from other people and projects.

To prepare, we took some time to really understand the problems we were trying to solve. We collected lots of user research, compared ourselves to competitors, analyzed usage data, and gathered insights from teams across the company like sales and customer support. We understood that people sometimes felt overwhelmed by Asana’s UI in general and now we had a list of specific pain points to back that up.

Next, we packed up our supplies and headed to a cabin on Russian River, where the five of us — two designers, a user researcher, our cofounder, and me — made ourselves at home. We woke up early to practice yoga. We cooked three meals a day together. We went jogging along the river. But most importantly, we got down to business.

Our home for the redesign kick-off

First, we did a couple of exercises to help us identify our target audience. We came up with a long list of user personas — planners, dreamers, doers, overseers, lurkers, etc. — and then picked which ones we’d target for this project. Based on our early research and our product strategy, we decided to go after the planners and doers.

We then studied their motivations for using project management software like Asana and tried to get a better understanding of their goals in general. We created detailed maps of the steps they took to achieve their goals in and outside of products like ours, which helped us identify the biggest opportunities for improvement.

Mapping out user flows

With these in mind, we explored different ways Asana could help them succeed. We broke off into individual brainstorming sessions where we each focused on specific workflows or use cases. For example, one person would think through different ways a planner could set up a project. Another person would come up with ideas for an invitation experience that serves doers relevant content as soon as they get into the product.

Sketch of our target personas and their workflows

We met together afterwards to share our ideas and riff off each other. There were lots of sketches, sticky notes everywhere, some rather complicated diagrams, and eventually… clarity.

Sharing sketches after brainstorm sessions

We left the woods aligned on our project goals and excited about the next steps. Our successful kick-off has inspired other teams at Asana to plan similar outdoor adventures and I hope you’ll consider it for your projects, too.

Stay tuned for more redesign musings, including sneak peeks!

If this sounds interesting to you, join us.

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