Remote Work: How to MAKE Your Boss Let You Work Remotely

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Remote work is the gold standard for most people’s office jobs. Tim Ferriss has a whole section on it in The Four Hour Work Week. Dozens upon dozens upon dozens of blog posts have been written about doing it. And the Basecamp guys even wrote a whole book on why companies should be entirely remote.

And if you can do it and do it well, you probably should do it. Offices are terrible for most non-management staff to get work done. They’re distracting relics left over from an era where the office was a counterpart to the assembly line. If you benefit from focused work, working from home will probably serve you better than working in an office.

But most of the advice out there on working remote is not very good. It either comes down to “get a job that advertises itself as remote” or “rip off your employer and just stop coming into the office.”

So, this is my quick-and-dirty guide to working remotely. This is based on my personal experience working remotely for most of my career, working on teams that are entirely remote, semi-remote, and being the only remote person on a team. And this is based on my personal experience with my private coaching clients.

A word of caution: Working remotely is hard. I do NOT recommend it for most people’s first or second job. I’ve done it for most of my career and think it is harder than an office job because so much of the accountability falls on you. If you are not conscientious, you should stay in an office until you can develop the conscientiousness to manage yourself well.

The Case Against Remote Work

To better craft your case for remote work to your boss, first understand the case against remote work. There are good cases against remote work, especially from a manager’s perspective. For just a second, ignore cynical interpretations like, “my boss just wants to breathe down my neck!” (if that’s the case, then you need to quit your job and get a new boss).

(If you want to skip to the nuts and bolts and the “how to,” just keep scrolling.)

Let’s assume your boss wants what is best for the company, isn’t a micromanager, and is still against remote work. Why might that be?

Remote Work is Hard

The most obvious case against remote work is that remote work is just downright hard. I really can’t emphasize this point enough. If you’re just starting out in your career, chances are you are just not ready for remote work yet.

It takes discipline to show up to your desk at home every day when you could be on Facebook or watching TV, or sleeping in and barely using your phone to stay on top of work.

Most people who have done remote work before know it is hard. It’s not all pictures of sitting on the beach using your laptop to “make money while you sleep” or anything like that (have you tried to use a laptop on the beach, by the way? It’s awful — don’t do it). If your boss has worked remotely before himself, he knows that it takes a lot of discipline and self-motivation to do it well.

You’ll have to prove to your boss that you’re disciplined, self-motivated, and capable of asking for help when you need it.

Remote Work is Hard to Track

Even if your boss isn’t a micromanager, he probably wants to track that you’re getting work done — especially if he has a boss. There are few things worse as a manager than your subordinates making you look bad.

While far from perfect, working in an office at least satiates this desire for the boss. He can walk by and see you doing something.

Remote work requires you to either have extremely high trust with your boss so that he knows you’re working, even if he doesn’t check in with you every few hours, or a system set up so that you can let him know what you’re up to. Tools like Slack will become your best friend.

Remote Work is Lonely

There’s a real human element to working in an office. And while that may not always be a great human element…

…it’s still a much-needed part of being a human being.

Remote work is lonely, especially if you don’t have other structured, community-based activities in your life. It’s easy to go a few days without interacting with people outside of your immediate family or your roommates. The dream of working from home in your sweatpants quickly descends into a nightmare of working from home in your sweatpants.

Lonely employees don’t feel connected to their colleagues, feel less motivated, and are more likely to misinterpret minor disagreements or points of confusion as major disagreements.

The companies I know that do fully-remote work well do regular off-site meetings, voice calls, video calls, and retreats to make sure teammates know each other, talk to each other, and build the relationships that usually exist in the workplace.

If you’re not at a fully remote company but want to work remotely, you’ll want to make clear that you’re engaged, involved, and less likely to just fall off the radar if you were allowed to work from home.

Remote Work is Not Conducive to Your Job

Remote work works better with some jobs than others. Jobs that benefit from long periods of uninterrupted focus, like writing and software development, greatly benefit from being at home and outside of the office. Managerial jobs and sales jobs, on the other hand, may benefit more from being around others and staying on top of the office day-to-day.

(One of my favorite essays on work schedules is Paul Graham’s Maker’s Schedule, Manager’s Schedule, here. While not about remote work, a maker’s schedule is much, much easier to pull off when you don’t have colleagues pulling on your collar at work.)

Most jobs can be done remotely, you just need to set up the systems and tools to make them easier to do. If you’re in ops, you’ll want to set up a receipt scanning system so you don’t need to be near an actual scanner. If you’re in sales, you’ll want to stay on top of your CRM. If you’re in marketing, you’ll want to stay on top of your product management system. But don’t be surprised if some bosses think certain jobs shouldn’t be done remotely.

Your Company Has Never Done Remote Work Before

Maybe you’re company has never allowed remote work before. Maybe it’s really traditional, or most of the employees work in labor and there’s just a handful of white collar employees who are expected to be in the office every day.

“Remote work” sounds scary to your boss. It sounds like something only tech companies and progressive, fashion-forward startups do. “It wouldn’t work for our company,” is probably what you imagine him saying when you ask if you can work remotely.

Here’s the catch…

Chances are your company has actually allowed remote work before, it just didn’t call it “remote work.” It probably called it “working from home,” like when there’s bad weather or you’re too sick to come into the office but well enough to get some work done.

With these common objections in mind, you can build a pretty quick case for your boss to let you work remotely.

The Nuts-And-Bolts: How to Land Remote Work

Landing remote work is less about putting together a proposal of “this is what I would do” and making a “pitch” and more about making sure your boss has no reason to say no.

Here’s the truth about work from the manager’s perspective:

Good help is really, really, really, really hard to find.

That sucks if you’re a manager or somebody charged with recruiting.

But it’s great for you, as the employee, if you can make yourself “good help.” Companies will fight each other for good help. This is how talent bidding wars happen. And that goes beyond just pay and perks like a fancy cafeteria or 401(k) matching.

Your boss will let you work remotely if the cost of saying “no” is higher than the cost of letting you do it.

As simple as that.

So, there’s two levers you can move here:

You can raise the cost of saying “no, you can’t work remotely.” This means you make yourself harder to replace. If you’re an average employee, anybody can replace you and the cost of saying “no” is pretty low. If you’re an outstanding employee, you’re hard to replace and the cost of saying “no” is much higher.

You can lower the cost of letting you work remotely. This means you assuage and preempt any concerns about remote work. You make their objections to remote work seem silly in the grand scheme of things.

This is how you do that.

1. Preempt Any Objections

Reduce the cost of remote work in your boss’ minds by making each of those objections at the beginning of the article seem silly in the context of you as the employee. You want them to say, “sure, remote work is hard, but I know you can handle it,” or “sure, remote work is lonely, but you’ve got a good grasp of things.”

Focus in on these three areas:

A. Build Trust

If you have strong trust with your boss, you won’t have to worry about Slack notifications all day, calls to see, “how are you doing?” and objections to you getting your work done from home. You want your boss to be comfortable with you doing what you say you’ll do and not have to check in on you.

Trust is built over time and through doing what you’ll say you’ll do.

Do what you say you’ll do. Do it on time and under-budget as often as possible.

And if you do need to ask for help, know when to ask for help. You don’t want to sabotage yourself by showing that you’re incapable of asking for help when you need it. Ask early and often. Take the initiative to get feedback. And get your work done.

Essentially, don’t give anybody any reason to think you’ll take advantage of them if you’re given some slack.

B. Show Discipline

Be disciplined at work. Show up on time, fulfill your duties, and be proactive. Be the first person to send calendar invites. Be the person who does the follow-up quickly. If you have down time at your desk, use it to prepare for meetings, calls, or get a head start on some of your work.

Essentially, don’t give anybody any reason to think that you’ll slack off if you’re not in the office.

C. Show Self-Motivation

One of the hardest parts of remote work is knowing what to do and when. Self-management is hard and most people can’t be trusted with it unless they show that they’re self-motivated.

Take the initiative to get started on tasks and projects that are in your purview even if nobody told you to get started on them. If somebody is complaining about a resource or problem at work, go find a solution, create the resource, or at least provide some kind of value from the meeting.

Essentially, don’t give anybody any reason to think you’ll wait around like a lost puppy if you’re not told what to do at every moment of every day.

2. Become Irreplaceable

Once you’ve reduced the cost of saying yes, you want to raise the cost of saying no.

In other words, you want to make it a no-brainer for your boss to let you work remotely.

Good managers want to keep their top-performers. And they’ll do almost anything in their power to do so if that top-performer is irreplaceable.

Become irreplaceable by making yourself a core part of your business unit.

The best way to do this is to be a rainmaker. Rainmakers are salespeople, fundraisers, and business development people who get cash in the door and do it well. The only times companies fire their rainmakers are when those companies are about to go under or those rainmakers undermine the company. That’s it.

One of my early mentors was a fundraiser for a nonprofit. He hated living where the nonprofit was based and just decided to move to another state after a certain date. The nonprofit let him do this despite having no remote employees at the time.

Why would they do this?

Because he was a rainmaker.

Not everybody can be a rainmaker, though. Maybe you work in marketing or engineering or management. The benefits you bring to the company are much less quantifiable.

In this case, make it hard to replace you. But do so ethically.

Pick up a lot of the tacit knowledge in the company. Make it a point to make yourself a fixture in the company and one of the only people on the team who has taken the time and has the initiative to ask to be cued into everything in your unit.

Learn about the culture of the team. Learn about your relationships with clients. Learn about niceties in your product (maybe you use X, Y, and Z WordPress plugins together, but you use them in a unique and weird way that nobody really understands except for you).

Pick up this tacit, institutional knowledge and be the go-to person for it. Document it (you don’t want to extort your employer — that’s unethical) so others can reference it later. But make yourself difficult to replace.

3. Firmly Ease Into It

Don’t ask your boss to let you work remotely.

If you do, you’ll get either a “no,” or “we’ll have to think about it,” and then probably an appeal to, “we can’t let people do that.”

Tell your boss you will work remotely.

Tell them exactly when you’ll do it, how you’ll do it, and what systems you have set up so that you can be just as productive working remotely as you would be in the office.

And then do it.

If you’ve established trust, shown discipline, shown self-motivation, and made yourself irreplaceable, your boss will have no choice but to say yes.

Ease into the remote work. Start with one or two days from home. Then pick up a few more. Be judicious. Come into the office when you need to. But know that you can get your work done, you’re disciplined, your boss trusts you, and you’re hard to replace.


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