The Manager’s Schedule Is Holding Back Remote Work

Here are the reasons it’s still tough for leaders to work from home

Luke Thomas
5 min readNov 4, 2019


Photo: 10'000 Hours/Getty Images

FFor some, the idea of working remotely is equivalent to laying around, watching Netflix (while working, of course), and going to happy hour by 3 p.m. For others, they can’t imagine driving into the office, being constantly interrupted, and leaving at the end of the day without a sense of accomplishment.

What causes this major difference in opinion?

If you’re trying to unpack the divergent views on remote work, you may start by considering the following variables:

  • Where do they work? Does their work culture support remote work?
  • What do they do for work?
  • Does their job require constant interaction?
  • How big is their company?

I’ve worked at remote-friendly companies with less than 10 employees and more than 150. I’ve seen smaller companies struggle with remote work and larger ones be very successful at it.

For a long time, I looked at the list of variables above and thought the most obvious limiting factor was the company culture. I still think this is partially true, however, there’s another major variable that flies under the radar. In fact, this reason may be one of the biggest contributors to why remote work isn’t more widespread.

And yes, I understand that remote work continues to rise in popularity, but I would argue it is still not as prevalent as it should be. This is especially true in the tech industry, which prides itself on hiring a diverse workplace but will only hire people who live within a 25-minute radius of the office.

The remote-friendly company — but only for a select few

I will periodically look at job boards and see that a company is hiring engineers for a remote-friendly position while all the other jobs are required to be onsite. Weird. Why?

Typically this happens because of the following reasons (at least, these are the ones I hear frequently):

  • The engineering team has a preference to work remotely
  • The company can’t hire enough engineers within a 25-mile radius of the office, so it is forced to look elsewhere for talent.

In this example, a particular team inside the organization is unlike the others. If the company culture is a key contributor to being remote-friendly, how does this happen? How does a team inside an organization that wants you to be in the office decide to allow one select group of people to work remotely?

‘I work from home, but only a little bit’

A recent study indicated that 70% of people work away from the office at least one day per week. I’m skeptical of this finding, but anecdotally it’s becoming more common to hear people say, “I work from home a couple of days per week, but I go to the office for meetings.”

I find this is more prevalent among non-technical employees. The boss allows remote work up to a certain point, but they can’t cross over into being fully remote. That would be too scary. We can’t have that!

Once again, the company culture isn’t fully supportive of remote work, but a particular team can periodically get away with it. How can this be?

The manager’s schedule is holding remote work back

Many people (especially the further you go up the org chart) operate on a manager’s schedule. For those of you who haven’t yet read Y Combinator co-founder Paul Graham’s article “Maker’s Schedule, Manager’s Schedule,” you should read it.

Key pieces are outlined below:

“There are two types of schedule, which I’ll call the manager’s schedule and the maker’s schedule. The manager’s schedule is for bosses. It’s embodied in the traditional appointment book, with each day cut into one hour intervals. You can block off several hours for a single task if you need to, but by default you change what you’re doing every hour.”

This may give clues into why remote work is so popular for engineering teams.

“Most powerful people are on the manager’s schedule. It’s the schedule of command. But there’s another way of using time that’s common among people who make things, like programmers and writers. They generally prefer to use time in units of half a day at least.”

“When you’re operating on the maker’s schedule, meetings are a disaster. A single meeting can blow a whole afternoon, by breaking it into two pieces each too small to do anything hard in. Plus you have to remember to go to the meeting. That’s no problem for someone on the manager’s schedule. There’s always something coming on the next hour; the only question is what.”

This article lays out two “modes” of work and they exist on a continuum. I made a graphic to help illustrate this idea:

The different modes of work.

The manager’s schedule thrives on in-person interactions. I’d argue that the key tools in the manager’s schedule toolbox are the power of observation, back and forth interactions, and at its core, extroversion.

Where the manager’s schedule goes horribly wrong is when activity happens, but there is no meaningful output.

The maker’s schedule thrives when the opposite occurs. It prioritizes output over activity. People-to-people interactions are not a dependency to getting work done. If people on the maker’s schedule tend to like remote work and people on the manager’s schedule don’t, how do we break down the barriers?

Making remote work more comfortable for the manager’s schedule

I fundamentally believe that in order to make remote work more of a reality, we need to address the elephant in the room: people on the manager’s schedule tend to have a lot of leverage inside a company, but they also tend to dislike remote work.

So how do we get them onboard with remote work so it becomes more of a reality for entire organizations? This may be a tall order, but I think we need to build stuff that takes the best of remote work and mashes it with the stuff that people on the manager’s schedule care about. With that being said, we need to preserve what makes remote work great at the same time.

Put simply, we need to be able to periodically “flex” across the continuum laid out in the graphic above.

For example, I’d argue that Slack is a tool that has made the idea of remote work much more realistic for people on the manager’s schedule. While it’s technically an asynchronous communication tool, it’s also used as an alternative to being in the same room, powering constant back-and-forth communication (which can be annoying).

On the other hand, remote work has its share of downsides, like the fact that people feel disconnected at times. A common solution to this problem is periodic meetups, which is an example of “flexing” across the continuum.

At, the company I co-founded, we’re building tools that make the manager’s schedule a bit more asynchronous. Remote work has downsides, but it’s all about finding the balance between these two modes of work and knowing when we need to flex. If we can do this, remote work will be much better.

Originally published at



Luke Thomas
Writer for

Founder @ Friday ( Mainer. Building an operating system for working from anywhere.