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3 ways to engage your boss when you're remote

During most of my time as a remote employee, my managers knew how to work with distributed teams. They were comfortable in direct messaging apps (yes, even pre-Slack!), and they naturally thought about team dynamics and plans that included the staff they couldn’t see on a day-to-day basis.

Out of sight wasn’t out of mind for those managers.

But then one day, there was a fairly sizable re-organization, and I began reporting to a leader in one of the main offices. I liked him a lot as a person, but he had little experience working with employees he didn’t see daily.

Prior to the reorganization, I had observed how he made decisions and led the team. Most of the time he simply dropped by someone’s desk to ask a question or called a person into his office for a conversation. He loved gathering people together in person for updates, meetings, and strategy sessions.

He also moved fast.

When he had to make a decision about something that wasn’t his area of expertise, he gathered experts in a physical room to brief him so that he could make a decision. Given his way of operating, it would be easy to miss insight from the people who were not in the office.

I was reporting to him in an operational role, assigned to manage special projects and general team operations, but how was I supposed to stay in lock-step with a person who moved quickly and fed off input of people directly in front of him?

After some trials (and many errors), here’s how I did it.

First, figure out how your manager takes in information.

Because this leader’s team had always been around him in person, he never used any messaging tools or video bridges. And asking him to use the PM tool we were using at the time? Forget about it.

You may have the best direct message, project management, or task management tool in the world, but if that’s not how your managers digest information, it’s on you to adapt. Yes, you may eventually get them to adopt your process, but you have to start by meeting them on their turf.

And, as much as it stinks, it may involve a little duplicate work. But there are ways to do this without too much additional effort (and a whole lot more impact!).

Second, keep yourself on your manager’s radar.

I realized quickly that I needed to develop ways to stay on my boss’s radar that aligned well with his working style. Here are a few tools and approaches I used:


One of these tools I developed was a simple “Top 10 list” in Google sheets. It’s fairly high level but provides a snapshot in time of what’s going on each week.

I knew my leader could look at this any time between calls to see what I was working on. More often than not, we used it as the first agenda item on our weekly phone call. I used this not only to share the big items I was working on, but also to guide a prioritization discussion if he added new projects to this list. Every time he added something new, we would look at that list together and figure out where it fit in light of the other projects.

It gave him a visual queue for what projects I was working on, their status, and how they fell in light of other priorities.

This tool helped provide information in the way he preferred it: short and easily digestible. But if I needed him to dive into the weeds on something, he could do it because he had the lay of the land.


Assuming you meet with your manager weekly (which you should! Set up time with them if they don’t set up time with you!), make the time as effective as possible by planning ahead and feeding them information ahead of time.

More specifically, managers who move fast often rely on their calendar for what they’re doing next. So when you set up a meeting, be sure to include—along with any conference bridge or phone number—the stated goal for the meeting and 3-5 bullet points of what you’re going to cover with them.

Putting this in the calendar invite instead of an email will allow the managers to have the information at their fingertips. This also puts you in the driver seat for how you want to spend the allotted time.

Helpful hint: Make the last agenda: “Anything else I missed?” or “Any news I should know about?” leaving the manager space to fill you in as well.


One other thing I figured out really quickly was that this leader didn’t read long emails unless he knew why he should read it and what action was required of him.

Some tips to ensure your manager reads and responds to critical emails:

  • Include a very brief “Short version” of the email at the top:

    • State the high-level question that needs to be answered or issue that needs to be resolved, and

    • The deadline for that answer.

  • Use short paragraphs. White space helps the reader skim your email for key points.

  • Use headers if the email is getting longer than 10 paragraphs or so.

  • If you’re describing a few options or issues, bold or bullet key phrases so the readers can skim first, then read in more detail when they’re ready.

  • Ask for a response by a certain date.

  • Clarify when you will follow up.

  • Clarify whether this issue impacts the current timeline.

Third, get to know the rest of the team really well!

The details behind this one are most likely a separate blog post, but—in short—you absolutely must build relationships with the rest of the team. Remember, when you’re remote and most of the team is in an office, you really are “out of sight, out of mind.”

Get to know your colleagues through Slack interactions, carving out time in meetings to talk about non-work-related topics, and—when you’re in the office—absolutely sit down with them in person.

The more bridges you build with your colleagues, the more you’ll have your finger on the pulse of what’s happening throughout the team, which will give you better context for what your manager may be handling on a day to day basis.

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