Managing Performance With Empathy

The Challenge

In early 2020, I noticed one of my designers struggling. Their solutions were overly complex and often missed the core value of the problem. Feedback from peers confirmed what I was seeing: they tended to overthink, move slowly, and deliver work that didn’t land.

The decline in confidence showed up in reviews as well, leading to a low performance score and eventually a performance plan. As their manager, it was my responsibility not just to hold the bar on quality, but to support this person as a designer and as a teammate.

Getting to the Root

We sat down to talk openly about their performance. I presented the feedback I’d gathered, but more importantly, I asked them to share their perspective. I wanted us to align on expectations and uncover what was really going on.

What emerged was motivation. They weren’t excited by small, incremental improvements. What they wanted was to build big, impactful features in nascent areas—fast. But when the reality of their work didn’t match that vision, they lost energy and fell into overcomplication.

Reframing the Work

Together, we reframed the challenge. Instead of waiting for one big, perfect project, we set up a structure around smaller ones. I asked them to create a plan that addressed their challenges directly, with goals, milestones, and specific skills to improve.

The biggest change was introducing tighter timelines and limiting exploration for smaller projects. This gave them constraints to work within and a chance to build momentum. I ensured their milestones aligned with the team’s roadmap and held weekly check-ins to track progress. We also built in feedback loops so they could hear directly how their work was landing.

The Outcome

The change was noticeable. Within three months, their speed and quality improved. They used the tighter timelines as a motivator and successfully got out of their performance plan. The team benefited as well—solution quality went up, and we shipped more.

But while performance improved, motivation didn’t. They still felt underutilized by focusing on smaller projects. We tried to create opportunities for them to work on larger initiatives, but we couldn’t find the right fit inside Dropbox. Six months later, they left for a role that better matched their aspirations.

What I Learned

This experience reinforced two truths of management. First, that structure, constraints, and direct feedback can help someone turn performance around. And second, that motivation matters as much as skill. Sometimes, even if you can fix performance, you can’t fix fit.

“You can help someone meet expectations, but if their motivations don’t align, the success may only be temporary.”