This Is What Impactful Engineering Leadership Looks Like

Jessica McKellar, former founder and now engineering manager at Dropbox, shares the tenets that have made her an effective technical leader.

What It Means to Directly Support a Team

“When you're a technical manager, your job is mostly about humans,” McKellar says. “There are two things you should always be thinking about: People's day-to-day and their year-to-year.” You should imagine every individual is traveling on both of these tracks at the same time. And as a leader, you can shape their experience on both to help them find a trajectory that meets their goals and your needs.

“On the day-to-day front, you want to make sure that everyone is happy, productive and engaged in their work,” she says. “This includes meeting with people regularly one-on-one and making the time and space to talk about any smaller issues they have or roadblocks in their way. It means whiteboarding a project to break it down into chunks, or walking a lead through a tricky interpersonal situation, or putting everything on pause to take a walk with someone who is having a tough day.”

You need to balance the efficiency of a structured weekly routine against having the unallocated time to give and receive feedback about the work in real-time. This alone can make you a very effective day-to-day manager.

The greater challenge is helping people devise a long-term plan for happy productivity at your company. There are many factors that go into this, McKellar says. But to simplify, half of it is raising people's awareness about what they want to do, and the other half is working that into everyday routines, planning and projects.

"You have to be intentional about working career growth into your broader engineering planning and execution of projects coming down the road,” she says. The really difficult thing is that not very many people have a clear sense of what they want from their job, and even when they do, they aren't forthcoming about it with their managers. Good leaders are experts at surfacing this kind of data and making it actionable.

“To develop a long-term relationship with an engineer, you have to learn enough about them to provide a framework to think through their career growth together,” she says. “You want them to articulate 1) the skills they want to improve, 2) the technical and non-technical experiences they want to have, and 3) how they want to increase the scope of their impact at the company.” Once they're able to communicate these things clearly to you, you're much more likely to find the right opportunities for them. And they're much more likely to recognize them.”

Your Team's Capacity = Your Executional Ability

Nearly all engineering managers remember their pivot — that moment when coding was no longer the number one priority. “I was an engineer and tech lead before moving into management, and I remember those early moments having to make the trade-off between writing the code myself and empowering someone else to do it,” says McKellar. “There's something really satisfying about directly, personally architecting and writing the code that will delight users.”

There's an inflection point when someone moves from engineer to manager, and it can feel very uncomfortable — like you're only in meetings and not getting anything done.

But the trade-off in stepping back from the code is that you then have the time to gather broader organizational context and execute on more strategic organizational investments, she says.

“At Dropbox, I have the opportunity to zoom out and think about the way engineering is done more broadly — the way we plan, the way we're structured organizationally, whether our tools set us up for success,” McKellar says. “Now if I spot an inefficiency, I have the time, space and global context to fix it.”

Keep this truth top of mind: If you can help the people on your team grow their individual capacity, you'll be able to get exponentially more done. This is all about matchmaking them with high-impact projects that align with their interests, the value they want to create, and how they want to grow. That's when motivation becomes organic.

Accelerate People with the Right Tools and Process

One of the reasons McKellar is excited to be at Dropbox is the size of the product and the challenges that come with it. “We're tackling infrastructure and product questions that usually face much larger companies,” she says. “That means that every engineer at Dropbox has the opportunity for huge ownership and impact. We don't have time to waste on things that aren't important.”

At the same time, it means that automation, tools and scalable practices are that much more important. This is a layered proposition for McKellar, who manages both team leads and a team of engineers herself. Planning is critical for both.

“For the team of engineers, I'm very involved in sprint-level planning for the team,” she says. “There's a process designed to engage everyone not just about the project at hand, but about how that factors into their future too. I have very explicit conversations with the people I work with about how they want to grow as engineers. That gets written down and incorporated directly into the planning process.”

In addition to managing engineering teams at Dropbox, Jessica McKellar is Director of the Python Software Foundation. She tweets at @jessicamckellar.