Published by Felix Hu - November 1, 2018

A weekly Design Rally to keep a growing team in sync

Setting time for designers to critique work, share empathy for users and recalibrate as a team.

Design Team at Calendly

When I was Calendly’s sole designer, I remember looking forward to the day when I could bounce ideas off of other designers. Fast forward to a five-person design team distributed across multiple squads, and I realized that my selfish desire to collaborate daily with designers would not scale for the benefit of the team. I couldn’t depend on neighborly questions and desk crits to keep everyone in sync, especially considering the demands of a rapidly growing startup.

Now, the design team gets together on a weekly basis for what we call a Design Rally. Every Friday, we spend about two hours sharing what we’ve made and learned that week and soliciting feedback from our design peers. Sometimes the meeting is short because individual work isn’t in a place to share quite yet, but often the meeting runs longer than the time we allotted. There’s plenty of design progress to review, followed by a flurry of questions and constructive feedback. Because each of the designers is working “heads-down” with their respective squad, the Design Rally is an opportunity to sync up on what’s going on in other parts of the company, and to ensure that we’re not designing in a silo.

Design Rally has morphed over the years as the company has grown. We’ve adjusted the format, weekly timing and how we choose to talk about our work, but the spirit of rallying as a team and growing together has remained constant.

Syncing the design team

Every Design Rally starts with a fire round of updates from each team member:

  • What did I accomplish this week?
  • What did I learn from users this week?
  • Of these, what would I like to present further with the design team?

After the fire round, we make a list of the projects everyone wants to present and prioritize their order based on how important it is to get the team up to speed and how much the designer needs feedback. If a significant user study was performed, we’ll stage that for presentation so that the methodology and learnings can be shared.

Providing critical design feedback

The feedback loop is already tight within our respective squads, but with other designers, we can go deeper into things that matter to us—like storytelling, process and systems. In presenting our work, are we communicating a story? Are we using our tools to their best potential? Are we proposing designs that adhere to our design system, or are we recommending improvements?

We share designs that we’re proud of, and also the ones we want to improve. Sometimes, if a designer has been working on a set of problems for a few weeks, they might start to feel like their ideas are getting stale. The Design Rally is a safe place for them to bring some of these challenges to light and reinvigorate the creative process in a supportive environment.

There are times when we don’t agree on a particular approach that a designer has taken, and we’ll debate the merits of alternative ways to tackle the problem. These discussions can get pretty heated in a room of passionate designers, but in the end, we’re all better for challenging our base assumptions.

What are we learning from our users?

The idea of sharing what we’re learning from users was not always a deliberate action item for each Design Rally. It was ad hoc. If we learned something that week, we would share it. When we started to ramp up research efforts across roles in the product team, there was a lot more customer interaction happening. We wanted to make sure we were taking the time to review and discuss the things we observed in addition to the formal logs we were reporting.

Calendly is used by people across multiple industries and organization sizes, so it’s useful to hear more about how our product is being used and the challenges our users face in their daily work. While millions of meetings are scheduled each month, we still care about the person trying to launch their small business. These individual cases help us to stay in touch with who our users are.

It can be easy to get lost in the pixels, but the adage is true that design starts with the user. Dedicating time to the user as a team helps to ground us in the basic principles.

Recalibrating with the rest of the design team

By the end of the week, a Calendly designer has been working with a lot of different team members and customers, and it’s nice to compare notes with other designers on what has happened. How is the rest of the design team’s work progressing? How does each designer’s work fit into the bigger picture? Are we all marching in step?

Perhaps most importantly, it’s time for each designer to remember that they are a member of a design team. Thinking back on the days when I was solo, this is what I really wanted: to be surrounded by other designers who are working towards similar goals.