Turning Struggle Into Growth

In Q1 of 2020, while leading design at Dropbox, I faced one of the more difficult parts of people management: helping a talented designer who was underperforming.

Over several months, I had noticed that one of my designers’ work was slipping. Their solutions were consistently overcomplicated, they were slow to deliver, and the final outputs often missed the core value we needed to ship. Confidence was waning, and feedback from peers reflected the same struggles. Previous attempts to coach them back on track hadn’t stuck, and eventually they received a low review score and landed on a formal performance plan.

As their manager, it was my responsibility to ensure Dropbox maintained a high-quality design bar. But equally, I felt responsible for their growth, morale, and clarity. The challenge was clear: I had to balance empathy for the individual with accountability to the team and company.

Getting to the Root Cause

I began with a direct conversation, not just to deliver feedback but to invite their own perspective. My goal was to align our perceptions of what wasn’t working. When we sat down, they shared that motivation was the deeper issue.

They didn’t feel energized by their current projects — smaller, incremental improvements — and longed instead for big, sweeping feature launches. In their mind, impact meant scale.

This insight reframed the problem. The gap wasn’t only skill or output; it was motivation.

Reframing the Work

We talked openly about how to approach the situation differently. Instead of focusing on one large project, I encouraged them to view smaller projects as opportunities to ship quickly, build momentum, and practice restraint. Constraints, in this case, could be empowering.

I asked them to design their own improvement plan: specific skills to work on, clear milestones, and goals tied to the team’s roadmap. Together, we agreed on shorter timelines and limited exploration for each project, ensuring they stayed focused. I committed to weekly check-ins and made sure to gather peer feedback so they could see where they were improving.

The Turnaround

Over the next three months, their approach shifted. With tighter timelines and smaller scopes, they moved faster, delivered simpler solutions, and regained confidence. Their performance improved enough to come off the performance plan. The team benefitted as well: solution quality rose, and we shipped more consistently.

But while performance improved, their motivations didn’t change. They still felt underutilized focusing on smaller projects. After six months, they decided to leave Dropbox for a role better aligned with their passions.

What I Learned

This experience taught me that performance management is as much about understanding motivation as it is about addressing skill gaps. By reframing the work and creating constraints, I was able to help this designer improve in the short term and leave on better terms in the long run.

For the business, it was a win: we shipped stronger work and maintained momentum during a critical period. For the designer, it was also a win: they left with clarity about what truly motivated them, and a chance to pursue work that better fit their strengths.

Not every performance story ends in long-term retention. Sometimes success looks like coaching someone through a rough patch, holding them accountable, and ultimately helping them find the right environment where they can thrive. That’s a reality of leadership — and one of the hardest but most important responsibilities of being a manager.