The journey of transforming chaos into peace

A few years ago, the Sync product and design team was in a challenging situation when we needed to create new user onboarding flows, as we were migrating to a new macOS file provider and needed to let users know how to enable Dropbox in this new OS. In addition to having multiple project leads, collaborating with different product teams, and working with an external design agency, we were also working on an external company partnership. I know, there’s quite a lot to unpack there!

Feeling pressured by time and circumstances, we fell into the the trap of iterating designs too quickly—so much that we sacrificed quality and the rich learning needed to elevate each iteration. Our weak points of view emanated from our lack of deliberate intent, and this made it difficult for cross-functional partners to come to a consensus on decisions.

This perpetuated a vicious cycle of exhaustion and misalignment as we worked tirelessly on a feeble foundation.

However, amidst this craze, our team transformed chaos into peace by growing from our mistakes. Keep reading to learn what worked well, how we pivoted from our state of tumult, and how we learned to build a more robust team and design foundation.

📢 Structured communication

What went well

• The core team communicated often and stayed on the same page as needs and strategy shifted
• We added more structure to reviews over time
  • We started creating an agenda with a recap of our last review, and an explanation of the kind of feedback we needed (high level, low level, etc.). This helped prevent the conversation from getting derailed.

What was challenging

• We had frequent reviews that didn’t always feel like the most productive use of time
• At times, reviews lacked clear direction or came at the cost of enough time to produce work that incorporated previous feedback
• Our direction with one of our internal design teams and external design agency changed multiple times
• Since one of our internal design teams was the liaison between our team and the external design agency, some of our feedback got lost in translation

What we learned

• Cancel reviews when work isn’t ready for feedback
• For more productive reviews:
• Start with a recap from last time because it’s easy to forget, but it also helps frame why the discussion is happening
  • Explain the kind of feedback needed
  • Prioritize feedback with decision makers, and clarify what’s a blocker vs. nice-to-have
• To help clarify the project vision with external creative agencies:
  • Show examples and artboards/key frames with annotations if you’re creating GIFs or visuals
  • Provide general principles and guidelines backed by previous research
  • Leverage the kickoff for collaboration between partner agency and core team

🛠 Strategy and execution

What went well

• I quickly built strong relationships with cross-functional designers
  • Made sure our product screens fit well in flows that were owned by other teams
  • Collaborated with other teams on design decisions, instead of deciding in silos
  • Kept other design team in the loop about changes in our designs
• We ended up with a solid design by our deadline
• Over time, we developed a stronger conviction about the business positioning that would best serve users

What was challenging

• We jumped into work on individual screens before fully understanding the user experience from start to finish
  • For example, we started working on the a smaller subset of the entire user flow without considering the other subsets. When we put them all together, it felt disjointed and too overwhelming
  • Product managers were split between different experiences in the same flow, which made it hard to keep the flow cohesive
• We narrowed our solutions quickly
  • We didn’t question our approaches until after investing significant amounts of work in them
  • This was partially caused by time pressure (we felt we needed to solve as quickly as possible)
  • We got tunnel vision on existing solutions and saw them as the only possibilities
  • This led to rapid user testing without precise hypotheses and truly distinct variants

What we learned

• Take the time to develop a strong point of view on customer needs before jumping into design and review
  • Keep in mind near and long-term business goals
• Create an end-to-end user experience that captures customers’ viewpoint, and reference it frequently
• Staff product managers to full, end-to-end flows to ensure a holistic user experience and reduce team confusion

🏋🏻‍♀️ Adaptability and resilience

What went well

• We were quick to respond to new information and brainstorm solutions
• When presented with a choice, we moved fast to resolve ambiguity and drive a decision
• Our mindset was “We, not I” throughout the project:
  • We were flexible about taking on work beyond our initial scope
  • We were quick to offer one another help
• Despite putting in long hours, we stayed positive and motivated to find the best solution
• While decisions involving our external company partnership kept changing, we didn’t fall into chaos—we structured our work even more

What was challenging

• New information revolving around the external company partnership was coming in daily, and the roll-out schedule was constantly changing
  • About four product teams working on the product release had to change directions again and again
  • It was difficult to track and remember decisions, and we kept revisiting them
  • We got feedback from several different channels, which became hard to track
• Multiple team members were new to Dropbox, and some partner teams hadn’t worked together before
  • Team members were learning how to navigate Dropbox while moving fast on this project
  • For example: Late in the game, we realized Design needed to be more involved in developing animations and stills with one of our internal design teams that was acting as the liaison with our external creative agency

What we learned

• For high-stakes, cross-functional projects, make sure there are enough experienced colleagues on the team
  • Colleagues with existing relationships and process knowledge can help newer team members navigate the challenges of these kinds of projects
• Create a design decision tracker that manages explorations and pivots
• Track requests from all parties in one place