From Remote Maker to Remote Manager: A Primer

The perks are touted and we all know them quite well, but there’s another side to remote work. It’s a side made of equal parts procrastination and rationalization—a continuous battle between choosing to do what you need to do vs. choosing to do what you’ve convinced yourself you need to do:

• Revamping the homepage copy vs. Vacuuming the house, again.

• Preparing for an All-Hands meeting vs. Oh, we’re out of coffee. I better go grab some.

• Updating the project Kanban board vs. I’ll just pop over on Twitter and see what’s new.

The situation might not always feel like a battle, but on remote work’s other side an individual must have the capacity to make disciplined decisions. Failure to do so can mean your productivity plummets even as you feel you’ve been working all the time; this is a result of work always being on your mind but not always top of mind.

The other side can also mean a life that feels out of control, where you have the need to defend yourself against anything that may disrupt your ability to focus—phone calls during the day, family asking for your attention when you’re in the middle of work, and of course your own mind’s easy drifting to tasks unrelated to work.

This is all amplified when you’re:

• Working for a progressive startup that values what you get done rather than how long you’ve been clocked in to do it.
• A newly-minted manager feeling the pressure of a new role and wanting to shine.
• Managing a remote team and trying to keep everybody on task and in sync.

First, let’s lay the groundwork for what is meant by “maker” and “manager.” A maker is a creator. Think of them as the writers or programmers on your team. A manager points the way. Think of them as the team lead or boss.

In Maker’s Schedule, Manager’s Schedule, Paul Graham writes that the maker’s schedule is “embodied in the traditional appointment book, with each day cut into one hour intervals.” Managers often switch up what they are working on or thinking about each hour.

For makers however, work happens differently. They typically need longer stretches of uninterrupted deep focus, which means even one or two meetings throughout the day can disrupt their ability to remain productive.

But there’s a special group that doesn’t get much love. They were makers, but they’ve become managers. They were depended upon, perhaps for a significant portion of their working life, for their creative prowess. They primarily lived in the cycle of taking directions and then executing beautifully.

Just looking at the scheduling differences, can you see how challenges could arise?

Great Maker to Stressed Manager

When I moved into an executive editor role at a growing media company, I felt those challenges first-hand. For starters, my instinct was to roll up my sleeves and create. When a pressing story needed to be covered in my first week on the job, I spent the day writing an article about it.

As a maker, this would have been me taking initiative and doing a damn good job. As a manager, this was me failing my team. As I later realized, I had several writers itching to cover the story. A few of them even sent drafts along that I didn’t see until late in the day because I’d been in deep focus mode.

The result was that my piece went live, but several others sat unpolished and therefore went unpublished. We had only mine, but we would have had three or possibly four stories—each one covering a different, important angle—had I been a manager and properly delegated.

That was a wake-up call, for sure. But there was a huge problem: I didn’t know how to take action on the wake-up call. And I wasn’t even entirely sure what questions to ask.

It’s only when I look back that I realize how much I learned from watching others on the executive team. They had spent years in managerial positions, and seemed to have a better grasp on things. Now, with hindsight and the space to reflect, here are a few questions I would have asked during my first few weeks:

• How much time should be spent delegating work to my 100% remote team of content contributors vs. thinking big picture about the overall company direction?
• How should I keep track of their project progress without micromanaging?
• When was the right time to gently push?
• How can I create a process for us to stay ahead of our editorial calendar while also granting our writers the periods of maker’s space they need to write when newsworthy topics come up?

A Few Project Management Basics, Remotely Applied

As the years went by, I established a few processes that were inspired by insights from those on the executive team and by some of the core tenets of project management. While I can safely say I answered questions like “Does remote project management really work?” (of course it can), here are a few basics that would have helped me during that early transition and that certainly help me now here at Flow:

1. Ask Lists Before Task Lists. Before embarking on any part of a project, it’s important for your team to have absolute project clarity. This sounds super simple, but when your colleagues are in different timezones and everybody loves the concept it’s crazy easy for a few go-getters to get cracking before there’s a plan in place.

Before any task, all questions must be asked. As the manager, it’s your job to present the project to your team of makers. But it’s also your job to seek feedback, and create the safe space crucial for your team to feel like they can ask questions about their role, the expected timeline, and the reasoning behind the overall decision.

I recommend trying to have synchronous meetings if possible. Regardless, keep all important notes (from meetings, team chat apps, etc.) in a single document and be sure to include who made the comment, and when.

2. Synthesize and Prioritize. When your team is informed on both the direction and their individual expectations, this is your time to draft a charter of the project for all to see. Whittle down the notes you’ve taken and the questions/feedback you received and share this more synthesized version of the overall project (with timelines and expected schedules) with your team. This is the manager’s time to be a maker.

3. Communicate, Address, Drive. Depending on the size of your remote team, this is your chance to check-in with each colleague to ensure they understand what the deliverables are and precisely how they’ll be achieved. Address any additional questions they may have, keeping in mind what you now know about the importance of the maker’s schedule. Lastly, give them the green light and know that your role from here on out will begin to shift from delegator to monitor.

4. Monitor and Maintain. It’s easy to stay too long in delegation mode, and this is what often leads to new managers (especially new remote managers) becoming micro-managers. They want to check in all the time, but this is typically more a result of their role insecurity than of their trust in the team. Get out of the way, trust your colleagues, and make sure you are monitoring progress (we use a Kanban board in Flow, but there are other methods). As you monitor, note when the project is veering from timeline expectations (it’s likely) and work to find solutions to keep the project on course.

5. Appreciate and Evaluate. As your team completes the project, sift through your notes, genuinely applaud your team’s effort both as individuals and as a team, and conduct a thorough project post-mortem. Our own Mark Nichols described project post-mortems like this:

On the surface, it’s a discussion about what went well, what went poorly, and how the team can be better. Under the hood, though, it’s an opportunity to remind your group that excellent team performance does not happen by accident—it’s a process that happens in increments, as a collective.”

For remote makers turned remote managers, it’s important to realize that in successfully being a remote maker you have already overcome some of the major hurdles of remote work. You’ve achieved high levels of disciplined decision-making, and you’ve learned how to listen and execute.

This experience grants you a unique perspective into how best to manage a team of makers. Couple this perspective with a framework similar to the basic project management ideas presented here and you’ll be well on your way to successfully making the transition.

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Illustrations: Bully