Remote Leadership

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I believe remote work is the future. I’ve been working as a designer for Automattic for three years and I worked from home half time the two years prior. Before that I did freelance work on nights and weekends at my dining room table. Working remotely allowed my wife and I to move from Philadelphia to a farmhouse in New York’s Hudson Valley two years ago. I hope to never move back to a city or commute to an office again. Remote is the only way I want to work.

To work for a distributed company as an “individual contributor”, in my case a product designer, was straight-forward. It wasn’t easy—it took diligence, strong communication skills, and a clear balance of work and life, but it was rewarding. I responded well to being evaluated on my output vs. my input and appreciated the flexibility that afforded me. If I was uninspired I ended my day early; if I had a moment of inspiration I didn’t have to wait until I was next in “the office” to work out my idea. I could casually stay up to speed while taking time off or I could just enjoy time offline.

That worked great until I decided to take on more responsibility and become the lead of one of our design teams. I’ve been in this leadership role for almost a year now and in certain ways I have found my footing, but in others I still struggle. For all the reasons remote work as an individual came easily to me, remote leadership is hard.

I can’t always see my teammates’ faces when I deliver instructions, feedback, or design criticism. I can’t always tell how they feel. It’s difficult to know if someone is having a bad day or a bad week. And I struggle most with measuring my impact as a leader in real time. I would like to “spend more time with my team” online, but we are spread across eight time zones. We work with developers from Bulgaria to Australia. I can’t be online all the time and I can’t give everyone the same amount of “facetime”. When I propose changes to our team design process, I can’t see their effect very quickly. Herein lies the biggest lesson I’ve learned from leading a team—patience .

My first six months as a lead I tried to be “highly available” to my team. I did one-on-one conferences every week with every team member. I worked longer and harder and when I failed to see the impact of my work I tried even harder. I didn’t understand why things felt so slow; I didn’t understand why it didn’t feel like I accomplished anything come Friday afternoons. Near the end of that period it started to crystalize for me, I was being impatient. I was used to much faster results—post an idea or a mockup or a prototype and by the next day feedback comes in. By the end of some weeks my design would be a pull request or already in production. As a lead my output is my team, their aggregate output, their happiness, and their professional development.

Despite that realization, I still lacked the tools I needed to help my team grow and the necessary patience to wait for results. At a bit of a loss I decided to ask my team for feedback. I sent all four designers on the team a number of questions via our anonymous feedback tool and heard from several of them that they would like to spend more time discussing professional development. I listened to them and started thinking about an approach to their advancement. Personal growth is a longer term endeavor than your average product design iteration and again requires patience.

It would make a better story if I could remember the exact moment I had my big leadership idea, but I’m afraid I can’t. At some point while pondering how to structure our one-on-one developmental conversations I remembered a project I did five or six years ago for the University of Pennsylvania. My firm (at the time) was contracted to help a group of doctors, researchers, and psychologists build a platform to facilitate behavioral economic studies. When designing interfaces for study participants I learned about the techniques these research teams used to modify participant behavior.

I recalled their weight-loss study design in particular. They would calculate the amount of weight a participant needed to lose and extrapolate by a safe “per week” weight loss amount. They then graphed that progression for each participant and provided them with a wifi-enabled scale. Each morning their weight was uploaded to the platform and if it fell below the “line” on their graph they were free to eat normally. If it fell above the line the app encouraged them to modify their normal behavior for the day—they could engage in some form of exercise, reconfigure their diet, or simply be more active that day. The underlying concept of the weight loss study was that small daily changes result in the achievement of a long term goal.

Remembering that study helped me “design” a process for my team development conversations that didn’t require them to reflect on a year’s worth of work at a time or recollect a dusty old project. Every two weeks I ask each designer four questions:

  • How do you think you’re doing the last two weeks?
  • What’s the thing you’re most proud of last two weeks?
  • What’s something you’d like to improve on in the next two weeks?
  • What do you want your role to look like one year from now?

The team reflects on the previous two week period and plan for their subsequent two weeks. If they are on the positive side of “the line” for the previous two weeks they can somewhat relax the next two weeks. As long as they stay on the right trajectory they will be where want to be a year from now. For some teammates that is a leadership role and for others each two week period of reflection lets them hone their craft or develop a new skill. Twenty six conversations and small inflection points ultimately add up to a year’s growth.

This approach to development is still an experiment, I’m still impatient, and I’m not entirely sure how to quantify my output as a lead. All I really need to do is show a little progress every two weeks and eventually I’ll get there. Remote work is an inevitable part of our future, but remote leadership remains a work in progress.


By Rick Banister

Designer at Automattic


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