Behind Outlook Mobile’s Design Week

How our quarterly design off-site inspires our process and lets us dream big

Designers, such as Charles R. pictured at the top, lead and facilitate the working sessions.

Coming from a design agency where I consulted for all sorts of clients and worked in a range of visual territories, joining the Outlook Mobile team presented me with exciting new challenges: how do you stay inspired when designing for a single product long-term? And how do designers get to contribute their voices to shape that product’s vision? The answer came when I experienced my first Design Week.

Every three months, designers and product managers from New York, Vancouver, Seattle, and San Francisco take a break from our day-to-day work to come together for a week of brainstorming, designing, and maybe even a bit of karaoke. Our leadership team spends time carefully curating a set of product themes for each day, and we give ourselves this time to feed off one another’s creative energies in-person and dream up blue-sky solutions for features that will eventually make it onto our product roadmap.

The week’s schedule

Day 1: Each Design Week kicks off with a day dedicated to learning. Most recently, we had our resident data scientist give a presentation on how we can take better advantage of designing with data. We can then apply what we learn to the concepts we jam on later in the week.

Day 2 & 3: Each morning, a designer and PM set the stage for the day’s theme by sharing out existing data, common user requests, and important UX problems we’re solving for. Afterwards, we break off into solo or group concept ideation and then design. We end the day presenting our concepts, with leadership and others abroad calling-in to watch.

Day 4: Field trip! This day is reserved for us to step away from the computer and get inspired through activities like taking to a ceramics class or visiting a museum.

The best parts of Design Week

1. We can think and design without constraints and as a result generate a ton of ideas.

During the rest of the year, it’s great that we work within well-defined scopes so that we can focus on solving core user scenarios. But it also means we generally can’t devote time to fully flushing out other out-there ideas. Design Week gives us a chance to go wild with our designs and to push the conversation around innovation with the rest of the team.

I’m also always in awe of the volume of concepts this team comes up with. I’ve experienced my fair share of these types of working sessions (which, like most take inspiration from this). I was used to the sprint that span over a few days and work toward a single prototype or idea. But Outlook’s Design Week investigates different themes each day that result in a handful of prototypes and even more concepts than we know what to do with.

2. Since upcoming product initiatives frame the day’s topics, our explorations can make a big impact.

Creating a better set-up experience and gratifying visuals helped more users take advantage of swipe actions.

For example, we knew discoverability and user trust in swipe actions were fairly low. The final concepts led use to explore creating more contextual teaching moments and making certain actions clearer to our users. Our ideas laid the groundwork for the improvements we eventually rolled out to the product: a more visually powerful swipe experience that helps people be more productive on-the-go. Since this update shipped in iOS (coming soon to Android), there have been an additional 12 million swipe triages a day!

3. Design Week encourages year-round collaboration.

Our Design Week explorations become valuable resources for each other during the rest of the quarter. For example, I was assigned to redesign the invitation overlay during my first few days on the team. We had data showing that users would attempt to RSVP to an event invite, but immediately exit the dialogue to view their calendar.

The final design added an embedded snapshot of your calendar, allowing you to better understand if you have conflicts so you can respond with confidence.

As I started researching the problem, I had access to several early Design Week explorations. Referencing these gave me a great starting point and a valuable introduction to how our designers approach finding simple solutions to complex problems. As I worked through my own explorations, I could reach out to each designer and ask questions about the ideas they had explored, making the process highly collaborative. This wouldn’t have been possible without Design Week.

Other key highlights

  • Team building: It’s a perfect opportunity for me to work with people I haven’t had the chance to yet, like folks from other teams. We occasionally invite one or two designers from the Outlook Web and Desktop to join so that they can bring their perspectives and gain insight to what the Mobile team is doing.
  • Being together: Because our design team is healthily distributed across North America, I look forward to us all being in the same physical space where we’re encouraged to be super creative and explorative. It’s a reminder that our team just clicks.
  • Inclusivity: Most importantly, Design Week makes Outlook Mobile’s planning process inclusive. Rather than it feeling like a top-down approach, it becomes a conversation that I and other designers want to contribute to. Even when Design Week ends, we keep the dialogue going on GitHub, where engineering, PM, and design are all empowered to voice their ideas.

What’s next?

Similar to how we’re always listening to feedback, learning, and iterating, we’re doing the same with team events like this one. We’re focused on keeping days energized but low-pressure, focused but also open, and productive but still fun. We also want to make sure the designers have enough time to create high fidelity visuals, but need to make sure product managers feel as involved in the ideation process. And even though this is ultimately a design-focused week, we know our engineers have interest in participating — how can we scale and expand without risking creating a “too many cooks” situation?

If your design team does something similar to this, please let me know in the comments what you’ve found works and doesn’t work. Or, if you have any questions on how you could apply this off-site with your team, feel free to send me a message on Twitter!


More on Microsoft Design

If you are interested in reading more about Outlook’s design process, check out this article by Miles Fitzgerald and this one by Siddhant Mehta. You can also read about the recently announced redesigned Office app icons and learn more about design at Microsoft on Medium.

Follow Microsoft Design on Dribbble and Twitter.


Written with 💌 and the help of Miles Fitzgerald, Charles Riccardi, and Michael Palermiti.