By March 4, 2020

Remote Work – Make It Happen in 4 Months

It may seem impossible to change your work situation while you are stuck in the day-to-day grind of a commute, but it’s entirely possible within four months to start working from home at least one day a week, on a consistent basis. Even better, you can do this and become more valuable to your employer.

What follows is a short breakdown of everything you need to do in the next four months to be able to work from home on a consistent basis.

It’s not hard to convince most managers to let you do this, provided you do the work. Think of this as a long sales process, rather than simply a way to approach asking a favor. You are asking your boss to allow you to drastically change the way you work—this takes more effort than simply asking for the privilege.

The process is organized as a set of simple tasks, broken down by month. The beautiful thing about this process is that it isn’t difficult or expensive.

Month 1

Primary Goals: Fix any issues with your home work environment and find management objections.

In the first month, your primary goals are to get rid of the impediments to working remotely.

Impediments to Good Work

While you might initially think your home setup is perfect for remote work, you’ll find a lot of irritating things over time that will hurt your productivity. If you don’t have a lot of experience working remotely, you may not anticipate some of the things that can happen (hence, this trial run).

Don’t learn the hard way; these challenges can include:

  • Noise problems
  • Distractions
  • Uncomfortable working environment
  • Technical problems
  • Communication difficulties
  • Problems with how you are perceived

Let’s break these down a little further and talk about some of the things you need to fix in your home environment. These are relatively easy to fix, provided you have prioritized remote work and have a decent working space.

Prioritizing remote work means you spend the time to actually set up a decent home work environment before attempting to work remotely. It also means that you make sure you try to anticipate any objections to remote work and deal with them before they become a problem. If you do not treat remote work as a serious priority, you’ll have a hard time convincing anyone to let you do it.

Create a Productive Work Environment

While many people have desks in their house, a lot of people don’t have good home work environments. In fact, most people’s home work environments are terrible for focusing and getting things done.

When you start working from home, you have to make a good impression if you want to continue being able to do it.

This means getting items out of the room that are distracting, especially things like gaming consoles and televisions, unless you are extremely disciplined.

You’ll also want to make sure that your desk is situated someplace where other people don’t regularly walk through, and where noises from inside (and outside) your home don’t regularly intrude.

Additionally, you need to make sure you have a desk and chair that are ergonomic, along with an appropriately powerful computer (unless you have a work laptop). You’ll want to make sure you have a good monitor, headset, and internet connection.

Remember, you are trying to convince your manager to let you work from home, so make sure you have the right tools for the job.

Know How To Handle Tech and Communication Problems

You should anticipate technical problems that can occur while working and have a plan for handling them. This can be as simple as having a place to go if your home internet stops working, or as complex as having a spare router in case your current router fails.

Equipment failures are something you can expect, and they make you look bad (if you handle them poorly). If, on the other hand, you are able to successfully deal with something like a network outage while working remotely, convincing management to let you work remotely more frequently becomes a lot easier.

You also need to have a plan for handling communication difficulties.

Nearly everyone has had an unpleasant experience while on a call with people who are outside the office. Whether it’s microphone difficulties, background noise, or software difficulties, conference calls are a frequent source of irritation. However, if you have prepared well, you can usually avoid teleconferencing issues.

First, make sure that you have multiple means of joining any conference call that you have on your schedule. Second, make sure that whenever you have a conference call, you try to connect well in advance of the meeting time. This will often give you time to fix any issues with your connection before they annoy your co-workers (or worse, your manager).

To be honest, technical problems hardly matter at all, so long as you can fix them before they annoy other people. Be prepared and you can do just that.

Counter Issues With the Perception of Remote Workers

Finally, we need to discuss the problem that is the hardest to overcome: Other people’s perception of your work quality and work ethic.

If management already has a decent level of appreciation of your work ethic and abilities, you’ll want to make sure that you continue to improve on that impression. If they don’t have a good impression of you (either because of prior performance issues or because you are new to them), then you should wait for a while before starting to advocate for remote work. While it is easy to feel like you have to start working remotely ASAP, you will be more successful in convincing management if you make a good impression first.

You also need to be conscientious of your behavior in the office. In particular, there are a few behaviors that you definitely need to avoid in the office so they don’t get mentioned when you start trying to convince management to let you work remotely.

You should:

  • Actively participate in meetings instead of zoning out.
  • Arrive on time or early, and avoid leaving early (or taking long lunches). While your productivity shouldn’t be measured by how long you sit in your chair, even the best bosses will often think less of you if they see that you aren’t putting in a full day’s work. This tendency is probably one of the best reasons to work remotely, as it neatly avoids this issue.
  • Not visibly browse the web or play on your phone during work hours. Even if you have nothing to do, you should try to look busy. The problem is that management tends to remember that you were goofing off during work hours, rather than remembering why you were goofing off during work hours.
  • Communicate effectively using whatever mechanisms you would use from home. For instance, you should be very careful to be clear and concise in your email and chat conversations if you expect to be using those tools remotely.

The idea here is to counter as many objections as possible before proposing remote work. While you can certainly counter these objections as they come up, it’s a lot easier if they don’t occur in the first place. Once you have removed the major and obvious roadblocks that keep you from working remotely, you can start doing trial runs.

Month 2

Primary Goals: Schedule a trial run and collect data. Get management feedback.

In your second month of this process, you need to schedule a trial run of remote work. At a minimum, a good trial run for remote work is at least a half day, and preferably longer.

To start, you’ll need a viable excuse for working from home. While there are a variety of things you could say, you should avoid lying about yourself or a child being sick. While you might be able to get away with it, lying makes the process more complex and adds stress. In general, you are better off just leaving a job at which you feel the need to lie.

The Trial Run

Instead of lying about being sick (or your kid being sick, if you have one), there are other perfectly good reasons that you might need to stay home while still being able to get work done. You probably have something coming up on your schedule already that you can use for this (or you can make something happen).

Here are a few options you might consider.

  • You have a doctor’s appointment close to home.
  • You have house guests arriving before the workday ends.
  • You need to leave right after work for an event close to home.
  • You are having repairs done on your home (or something in it).
  • You are meeting friends for lunch close to home.
  • Weather or environmental conditions make it difficult to get to the office. Depending on where you live, this could be anything from snow, to heavy rain, to construction and other events causing traffic problems. The only downside to this one is that you don’t control the weather.

Any of the above suggestions will likely work. This does several things for you. First of all, it gives you the opportunity to actually test remote work with fewer risks than you might experience otherwise because it is for a limited period of time. Second, it gets your boss involved in the process of allowing you to work remotely—this tends to create the sort of buy-in that helps get them on your side later when you want to work remotely more often. Third, it lets you test your boss’s disposition toward the idea of remote work in a way that surfaces objections without directly suggesting anything (yet). Ideally, such an approach means that your boss considers the possibility of you working remotely on a regular basis before you ever bring it up.

Evaluating Your Results

Once you have authorization to work remotely on a one-time basis, you need to do a little bit more than just working remotely for a single day and then going back to the office.

In particular, there are several questions that you need to answer in the affirmative. If the answer to any of these questions is “no,” then you will need to fix the issues before proposing regular remote work. Here they are:

  • Were your co-workers and your manager able to get ahold of you when they needed you in a timely fashion?
  • Were you able to participate in meetings and conference calls, including being heard/seen, seeing/hearing other people, and being able to see anything shared on screen?
  • If you had a meeting or conference call, were you able to join and participate in the call in a reasonable amount of time?
  • Were you able to get your work done in a similar (or lesser) amount of time than what would be required in the office?
  • Were you able to get in contact with co-workers, your manager, and any other external parties you needed to reach during the course of the day in a timely fashion?
  • Were you comfortable working in your home office?
  • Were you able to handle noise and other distractions?

If the answer to any of these questions is anything other than “yes,” then you still have some work to do in order to have a good remote work environment.

Don’t worry if you didn’t anticipate everything—that’s why you are doing a trial run in the first place. You want your remote work setup to be resilient, and this approach allows you to discover anything that might be a problem before it derails you.

Management Feedback

You should also touch base with your manager regarding how the remote workday went when you return to the office. It’s important when you do this that you don’t start talking about working remotely on a regular basis. If they bring it up, that’s fine, but it’s not time for you to do that yet.

The last thing you want to do right now is to start a discussion about regular remote work. This is especially true if you experienced any problems on the previous day. Instead, you should get your manager involved in the process of improving your remote work environment.

It may seem like a lot more work, but if you involve your manager in the process of making you more effective at working remotely on your trial run days, it will help you achieve management buy-in when it comes to asking to work remotely on a regular basis.

This approach will also help you determine management’s general disposition toward remote work and learn what problems will be most important to them.

Month 3

Primary Goals: Schedule another trial run, and collect more data while dropping hints about working remotely more often.

In the next month, you should do another trial run (or better yet, two trial runs) of remote work, using what you learned in the previous months to further improve your productivity while working from home.

This time, however, your goal is not just looking for ways to improve your remote work environment (although you should always be doing this). Rather, your new goal is to exceed a normal day’s work while working from home. Depending on the type of work you do, this could be a very simple process, or it could be rather difficult.

For instance, if office interruptions are wasting a lot of your time, you should be able to easily exceed a normal day’s productivity at home, simply because you aren’t being interrupted all the time. However, if technology issues are slowing you down, and you experience more of them while working remotely, you’re going to have to put in a lot of time and effort to get rid of those issues.

Monitor Productivity

While you work toward this goal, it’s best to exceed a normal day’s work by 20% or less. Though you may well be capable of doubling your “in-office” numbers, it’s ill-advised to let management know that.

Managers tend to set expectations around your maximum capacity, rather than your sustainable capacity, so you want to make sure that your productivity doesn’t drop at a later date as remote work becomes routine. Remember, you can always improve the impression you make later, but you can’t afford to make it worse later.

Keep thorough notes on your progress, and share this information with your manager. Ideally, you can show them that you are more productive when working from home.

Plant the Idea of Future Remote Work

At this point, you can start dropping hints about possibly wanting to work remotely more often. If you are lucky, proving your productivity will be enough to get the green light. This can work if your manager has enough power to make the decision themselves.

However, many people are not so lucky. Frequently, your manager has to justify remote work to people further up the chain of command. This is part of the reason that you collected data in the previous steps—this makes it easier for your manager to convince their manager.

Dropping hints will do a couple of things for you. First, it will help you gauge how receptive your manager is to the idea of remote work. It’s entirely possible that you will find out that management is completely against the idea of regular remote work, regardless of any proof of its benefits.

If that’s the case, this sort of hint will warn you in advance so that you can start looking for a different job. On the other hand, you might find that your manager is really on board with the idea of remote work, in which case you can start working with them to make it a reality.

If your manager is on the fence about the idea (or if their manager is), dropping hints will help reveal any additional objections management has—you’ll have to handle these if you want to work from home.

Month 4

Primary Goals: Propose a single day of remote work per week on a consistent basis.

Finally, a mere four months after starting out, you are ready to suggest remote work on a regular basis. Now that you’ve proven that you can work effectively from home and have some degree of management buy-in, it’s time to make the suggestion.

However, you still have to be careful how you do this. A lot of people fail miserably at trying to set up a work-at-home arrangement because they pitch the idea in ill-advised ways. This is still a sales process, and you haven’t closed the deal.

How To Effectively Pitch Remote Work

I’ve watched a number of people try to convince management to allow them to work remotely and have noticed that there are a few types of mistakes that people make in general. I’m going to explain these as a list of ways that you can screw up and what to do instead.

Taking a cue from the old Goofus and Gallant comic strips, I’m going to describe these as sucks and succeeds because that’s exactly what these two respective approaches do.

  • Sucks: “I’d like to work remotely two days a week so that we don’t have to pay for child care on those days.” Succeeds: “I’d like to work remotely on Tuesdays and Thursdays so that 40% (two weekdays) of my work time is spent deeply focused on critical work items.” Phrasing it this way helps make potential improvements less vague by putting actual numbers around the percentage of your time that will be more deeply focused.
  • Sucks: “I’d like to work remotely one day a week so that I can go to church on Wednesday night.” Succeeds: “I’d like to work remotely on Wednesdays so I can get more done before our release deadlines on Thursdays.”
  • Sucks: “I’d like to work from home two days a week so that I can avoid rush hour traffic.” Succeeds: “I’d like to work from home on Wednesdays and Fridays so I can start earlier, when I do my best work.”

You’ll notice several things in these two approaches. First, the approaches that fail tend to express the upside of remote work in terms of what it does for you rather than in terms of what it does for your employer.

The second issue with the failing strategies is that they are too general—they talk about just working remotely, rather than specifying days of the week. While the former is more obvious, the latter probably bears a bit more explanation.

The reason you want to be specific about which days you want to work remotely is twofold. First, if they argue about the day, they’ve already accepted the premise of remote work.

Second, they can quickly and more easily visualize how your absence from the office will impact the rest of the team. If you’ve picked your day right, that makes everything else easier. If not, it ensures that the conversation is focused around which day you can work remotely instead of whether you can work remotely.

After Month 4:

Primary Goals: Start working remotely, but keep eliciting feedback from management.

Even once you start working remotely, your task is far from over. If you find this change to your lifestyle positive and would like to keep it, you still have a lot to do. In particular, you need to make absolutely sure that this arrangement continues to work for management.

You cannot rely on management to tell you that things are not going well, as many managers will suddenly encounter a “last straw” and decide to abruptly change your working relationship.

Further, because you are working remotely, you won’t be around the office to notice if your absence is causing problems. It’s very easy to get blindsided.

Communicate With Management

If you’d rather not go through your workday with the sense of dread that you are going to suddenly lose your remote work privileges, then you’re going to have to spend time and effort making sure that management remains happy with both your performance and your interactions with the rest of your team. Both things have to work, or you will eventually get a rather nasty surprise.

The first is best handled by regular communication with your manager. Don’t make the mistake of being subtle here—it’s best to be direct and ask how things are going (and what you can do better).

There are two useful points here. The first is that this is a good way to head off problems before they occur, and the second is that this also gets your manager involved in improving your effectiveness while working remotely.

When someone participates in improving your results, they tend to be more invested in those results. This will help you out a lot if, for instance, your manager’s manager starts questioning the remote work arrangement.

Don’t Forget About Your Co-workers

When in the office, you should take time to touch base not only with your manager but also with your team. You need to make sure that you maintain good rapport with your team, are timely in helping them out when they need it (whether you are remote or not), and that any concerns they have about you working remotely are handled.

If your co-workers are favorably disposed toward you, and you aren’t causing problems for them, they are far less likely to cause problems for you.

There is also the converse of this—if your co-workers are irritated that you are working remotely, and you are making their jobs harder by doing so, they will create problems for you eventually. Spend the time and effort required to make sure that you aren’t hindering their productivity when you are out of the office.

It’s Easy To Convince Your Boss

It’s really not hard to convince management to let you work from home. However, if you simply ask without doing the work up front, you are more likely to meet resistance.

Convincing your boss to let you work from home is not convincing them to be kind or be charitable; it’s a sales process and needs to be treated like one. If you prepare adequately and are able to handle management objections, the process can be a smooth one.

About the author

William Gant

William Gant is a software developer who has been working in the industry since 1998. He has worked with dozens of different programming languages in a wide variety of programming environments, as both an employee and as a consultant. In addition, he has owned his own business, been heavily involved in several startups and is currently half of the Complete Developer Podcast, among numerous other things in the development space.