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Trello’s Justin Gallagher on Remote Management at Scale + More

Effective Leadership Series

Justin Gallagher is the Head of Product Management at Trello. He helped design and build the very first version of Trello and launched the product at TechCrunch Disrupt in 2011.

We got to know Justin when he spoke at last year’s Design Driven event in New York and shared Trello’s approach to remote-enabled product and design. Not only has Justin been influential in building Trello from the ground up into the high-powered, easy-to-use application it is today, but he also manages a large team of product managers, designers, and more. We caught up with him to hear more about his management journey, leadership tactics, and more.

What was your first management role and what did you learn from it?

My first management role was in consulting before I started working in tech & startups. It was a people and project manager role. I learned a ton about working with people — both those I was managing and also the clients we were working for. From that first role, I learned how to manage expectations, how to align the work we were doing with the strengths of individuals on the team, how to build trust, and how to be humble.

Early in your career, before assuming leadership roles, what was one quality you appreciated in a great manager and what’s been the most memorable framework that you’ve adopted from a past manager?

I’ve been very lucky to always have managers who cared a lot about the people working for them. I had friends who didn’t have the same experiences. Talking with them, I really grew to appreciate managers who always put their people first.

Justin speaking at Design Driven in June, 2017

One manager I worked with in the past used to say that “people’s strengths are their weaknesses.” I don’t know if this counts as a technique or framework, but I try to think about each person’s individual strengths and understand how those might also manifest as weaknesses. Then I try to ensure that people are contributing in ways that capitalize on those strengths and avoid those same weaknesses.

As a simple example, someone who’s really good at communication and project management might be great on a complex, cross-team project. At the same time, their structured style might bog down a small, creative team trying to create a new product from scratch.

What are the most important daily or weekly habits that you’ve developed as a leader?

I have a Trello board (no surprises there!) that I use to keep track of everything I need to do. I use it to make sure I stay on top of the many projects, meetings, emails, and other things I need to deal with every week. I literally couldn’t get through my day without it. I actually wrote a blog post (below) about it.

To make sure I’m prepared for the day ahead, I spend a few minutes every morning on the train going through the items in my “Today” list to make sure they all have an actionable next step. This helps me keep up the momentum so I don’t get bogged down by big, overwhelming projects. For meetings and 1:1s, this exercise ensures that I go into every conversation with at least some forethought and preparation so I can make the most out of that time.

What’s one other tool that you can’t live without and why?

I read somewhere that taking notes by hand helps with retaining and processing information. So, I’ve been using Notability on my iPad (with the Pencil) a lot recently. I’ve really been enjoying it. It syncs seamlessly to my phone and laptop too, so I don’t worry about losing or forgetting my notebook like I did when I took notes on paper. The ability to change line weights and highlight colors makes it easy to create cool-looking notes, which keeps me entertained while I’m jotting things down.

A lot of what I do now is look over written work, specs, and designs. I create PDFs or screenshot things from my computer, paste them into a note, and then annotate them on the iPad. It’s a nice combination. Also, Notability has great handwriting recognition and search functions, so I can still use search to find things in old notes like I used to do when I typed everything up. For example, I write “TO DO” next to things I want to come back to. When I want to figure out what I need to follow up on, I just search for that phrase. I’ve had to tune up my handwriting a little bit to make it work, but that’s probably a good thing.

What framework do you use for your one-on-one meetings?
I keep my 1:1s pretty casual and conversational. Our team is majority remote, so for me, these meetings are as much about building relationships as they are about checking in on projects, performance, and career aspirations.

In general, I try to be a good listener and let the other person talk more than I do. If there’s something important I want to check in on or a problem that needs to be addressed, I’ll give a heads up before the meeting so I don’t catch people off guard, and they have some time to prepare if needed.

1:1s are as much about building relationships as they are about checking in on projects, performance, and career aspirations.

Double-clicking on remote management, what would you say is the most important piece of advice you’d share with other managers who have remote employees?

I’m often asked how I make sure remote people are actually doing work. In my experience, that is never a problem. The people we hire are smart, talented, and motivated to contribute. The main things they’re missing out on are the camaraderie and information that in-office folks obtain from just seeing each other around the office or chatting over coffee. As a result, I focus my efforts on making sure remote people feel like they’re a part of the team and ensuring that they have the right context to operate in and make decisions.

To enable everyone to contribute equally, we essentially function as a fully remote team. For example, we avoid piling people into a conference room for meetings unless every attendee is in the office. As a rule, if one person will be joining the meeting remotely, everyone joins from their laptops at their own desks. We do this even when several folks are connecting from our office. This gives that remote person the ability to contribute equally instead of relegating them to being an observer on the TV on the wall. We also carve out the last 10 minutes of our team’s weekly meeting for socializing since we don’t see each other in person every day.

As a rule, if one person will be joining the meeting remotely, everyone joins from their laptops at their own desks.

Is there someone who you really admire as a leader (not at your current company) that you think would enjoy being interviewed?

Let us know by sending their name and short description to jack@firstmarkcap.com.

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