When is Remote Working a Bad Idea? Here are 4 Scenarios.

Michael Dabrowski
willu
Published in
6 min readNov 3, 2017

A location-independent job can provide you with loads of benefits, depending on where you’re at in life.

But once the honeymoon period subsides, will it still leave you jumping for joy?

The biggest perks for the 20–30 year old crowd include the ability to travel, communication development, and help with building behavior-based work habits (e.g. do you know what gets you in the mood to be productive?).

If you have children, not having to stress out about a daily commute on top of getting the kids ready for school or daycare is likely worth thousands of dollars per year.

Most people, however, don’t find themselves in a 100% remote situation.

That’s probably a good thing. Because from my perspective, most companies aren’t built for it. And their employees aren’t ready for it.

Have you ever felt your quality of life would increase if your company started to let you “work from home”?

The truth is this: maybe it would. But maybe it wouldn’t.

That said, if you feel strongly enough to broach the topic in your 9–5 butts-in-seats workplace, here are some cautions that — if true — will leave you fighting an uphill battle.

So be careful. Convincing and/or implementing a remote work situation might not end well.

Without further ado, when is remote working a bad idea?

#1. When your company doesn’t have the right foundation

In this day and age, there’s no shortage of company leaders who are open to the concept of working-from-home. Flexible work arrangements aren’t quite the norm, but they are commonplace.

Here are just a few remote-forward companies, along with their stance on the remote-work environment they’ve created.

There’s a ton more out there. They’re not hard to find. Are they difficult to get a job at, though? In general, yes. That’s because they have a wider pool of candidates to choose from (and more people applying).

Read through their about us pages. You’ll see they all have a very specific way of approaching work and life. They also select for candidates with highly targeted skill sets. Generalists tend fail out of their jobs at remote companies.

The crux of the matter is that these work processes were built precisely to support location-independent work.

Most companies aren’t set up this way, so you’ll encounter process and workflow issues when trying to work remotely

Consider for example, a couple identifying qualities of your average startup:

  • Things are constantly changing day by day
  • Repeatable processes haven’t been built out. Nor should they, until it makes sense to

Faced with these issues, as much face-to-face communication as possible is likely the best solution.

If you belong to an older and more established company, your internal communication tools might not be optimized to handle remote work. Tools, by the way, aren’t difficult to learn. A surprising amount of work can be accomplished using just Slack, Google Docs, and Google Sheets.

It’s the adoption of new tools and workflows (across leadership and employee teams) that takes significantly more frustration and effort to implement than one might imagine.

These are the sorts of process and workflow challenges you’ll run into with companies who lack a solid remote-work foundation.

These issues might seem easy to navigate, but trust us — they aren’t.

#2. When you don’t have highly skilled, A+ players on your team

When it comes down to it, an A+ player just means someone who has a high IQ and/or high levels of conscientiousness, or diligence. Those personality qualities, above all others, are the best predictors of success in the workplace.

Two Important characteristics of remote workers

This is how someone with a high IQ and high levels of conscientiousness acts in the workplace:

  • With proactivity and brute effort

Simply put, these sorts of people take an active approach to problem solving. They identify areas needing improvement (e.g. in work, in their behavior, in others) and set out to fix them. Immediately.

You can rely on them, because they’re consistently engaged with each and every work initiative they take on.

Further, they know how to motivate themselves — an essential quality when it comes to being committed both the overall picture, as well as the small details.

  • With a commitment to highly-specific, written communication and documentation

These types of folks are able to structure their thoughts into a nice little package for easy and pleasant consumption.

Whether the emphasis is on the end user, their customers, their teammates, or their superiors — they’re constantly oriented toward how their communication efforts are coming across.

In practice, you can spot someone like this if they routinely communicate complex ideas with clarity, brevity, and a good-nature. For some, this comes naturally. For others, they’re able to accomplish this with sustained effort and attention to detail.

Either way, the end result is rare enough that others notice when someone’s able to write well.

Both of these characteristics are absolutely essential to a remote work environment. If there are people on your team who don’t embody these characteristics to their core, there’s little hope that your distributed team will have much luck functioning without serious headache.

#3. When you’re trying to turn your job into something it isn’t.

If your job doesn’t function remotely, you have a couple of options:

Option 1: Leave

If you’re worried about convincing your bosses to let you work from home, the best thing to do might just be to find another company to work for. In the US, there are…quite literally…hundreds of postings made to job boards daily.

Keep in mind, if that’s your only strategy and you don’t have a highly targeted skillset, you’re likely to be ignored. As mentioned before, these postings receive many more applications than your average posting for an in-office position. So, you’re less likely to be successful if you only target remote job boards.

Boost your chances by:

  • Targeting a specific niche you have experience in or insight into
  • Learning how to be effective with cold emails. Be straightforward, empathetic, and excited
  • Finding your edge — whatever that means to you

Option 2: Make a business case to start working from home

Be very careful with this one. It’s very possible you come off as inarticulate when conveying your ideas about remote work, and if that happens — your bosses might question your commitment to the team. Things will go downhill from there.

Even if they do end up letting you try it out, and you’re the only one on your team who starts doing so — that’s likely to spring up jealous feelings (e.g. “why do I have to come in the office and they don’t?”) among your co-workers.

Whatever you choose — if you must take this route (I probably wouldn’t recommend it in most cases), it’s essential that you focus on the business case for it, and nothing else. Do not make the conversation about you whatsoever.

Maybe it’s because your company needs a lot of writing done, and you need creative freedom to run that work effectively. That’s a possible explanation that could be argued for. And your coworkers can understand that.

Still, if your office is primarily…in office, don’t think you can just run off to a beach in Thailand while the rest of your crew has to put up with the winters of Minnesota. It probably won’t work out.

Unless you pitch a deal to become a 1099 contractor. I’ve seen that happen and work out well for all parties involved. But then you give up on job security and income sustainability. Plus you’ll have to pay more taxes. (Ah, the realities of self-employment.)

Also realize once that happens — congrats: you’re now an entrepreneur.

#4. When you want to be pushed to grow

Remote, 9–5 positions can hinder:

  • Active learning

I’ve heard many a story of managers getting cushy and comfy in their stable 9–5 work-from-home jobs year after year. When suddenly, the company makes cuts, and because they only carried out routine tasks without a focus on bettering themselves — they struggle to regain employment.

There’s no way around it: being in the office opens you up to rapid on-the-job-learning and career advancement.

  • Your social life

If you aren’t good at naturally seeking out friends and arranging social engagements with new acquaintances, you will definitely struggle with a 9–5 remote job. This is the sort of thing that creeps up on you over time. Not that you should be best friends with people at your office, but routine social interaction (opposed to very little) is preferable when it comes to your mental health.

To wrap this up: there’s certainly no question remote working provides significant value to certain types of people, during unique points in their life. But there is reason to be cautious.

Especially since it’s become somewhat of a trend to endlessly tout the benefits, without mentioning potential pitfalls.

If you are committed to making a location-independent role work for you — go in knowing the pros, cons, and have a plan to navigate each of them.

Good luck!

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