Sometimes the hardest thing for a team isn’t the work in front of them—it’s the absence of work ahead.
In Q1 of 2021, I returned from paternity leave to a newly formed group at Dropbox called OATS (Onboarding, Activation, and Teams). It was a big group, about 70 people, but two of the teams—roughly 16 people—were facing a hard cliff: in six months, they would run out of meaningful work.
The impact was obvious. Leadership was worried about delivery, and the teams themselves were feeling morale issues. Without clarity on their future, the energy was draining out of the room.
Diagnosing the Problem
These teams were new, with roadmaps they had inherited rather than shaped. They lacked planning leadership, and without fresh opportunity development, the pipeline was thin. It wasn’t a lack of talent—the skillsets were strong—but they were missing the structure to channel that talent into future impact.
Taking the Lead
I wasn’t directly responsible for their roadmap, but I was accountable for morale, outcomes, and impact. So I proposed stepping in to lead the process.
I started with principles, which I ran by my PM and Engineering partners:
- Think long term.
- Develop a mixed portfolio.
Together, we refined those principles into a working model: fix planning for now, fit planning for later.
Actions
I began with a listening tour to understand the teams’ skillsets and frustrations. From there, I designed a short-term ritual we called vision sprints—week-long, design-sprint–style workshops where teams could generate big ideas, scrutinize them, and test them quickly.
At the same time, I codified a longer-term planning process in collaboration with my PM partner. We refined it with design and product leads, then delegated responsibility: design leads ran the vision sprints, while PMs codified the long-term planning structure.
"When a team feels stuck, you can’t just give them work. You give them tools to create their own momentum—short-term spark and long-term structure."
Results
The change was immediate.
- The teams ran five separate vision sprints, generating a wide set of opportunities.
- Data science, research, and PMM partners applied high-level sizing, which allowed us to prioritize ideas and cut those without evidence.
- The teams landed on a mixed portfolio—some foundational research, some medium-priority projects, and clearer longer-term bets.
- The long-term planning process didn’t just solve a short-term gap; it was codified at the group level.
- Vision sprints became a repeatable tool—something we could use again as a “band-aid” whenever planning hit a cliff.
Most importantly, morale shifted. The teams could see a future again. They weren’t waiting for work—they were building it.
“They weren’t waiting for work—they were building it.”
Navigation Summary
How I turned two stalled teams at Dropbox into idea-generating engines by introducing vision sprints for short-term momentum and codifying long-term planning for sustained impact.
TLDR (Audio Transcript, ~2 min)
When I returned from paternity leave in 2021, two teams in our newly formed OATS group were stuck. They had a six-month cliff of no work ahead, morale was sinking, and leadership was worried about delivery.
The problem wasn’t talent—it was planning. They had inherited a roadmap without opportunity development and lacked structure for what came next. So I stepped in to lead.
We agreed on two principles: think long term and develop a mixed portfolio. In practice, that meant fix planning for now, fit planning for later. I created a short-term ritual we called vision sprints—week-long workshops to generate and test new ideas—and codified a long-term planning process with my PM partner. Design leads ran the sprints, PMs codified the planning, and I stayed aligned with leadership.
The results were strong. The teams ran five sprints, generated opportunities, sized them with data partners, and built a balanced portfolio of projects. Morale recovered, impact grew, and both processes stuck—vision sprints became a reusable tool, and long-term planning was codified at the group level.
The lesson for me: when a team feels stuck, you can’t just give them work. You give them tools to create their own momentum—short-term spark and long-term structure.