In a previous post, I discussed the major tailwinds that are contributing to the rise of remote work.

Now, I'd like to outline the factors that are preventing the rise of distributed work. Before I dive into these restraining forces, here's a brief disclaimer:

• Each company is different and there is no one-size fits all solution. Some teams and organizations will thrive in a remote setting, while others will not.
• This article assumes that there are people in your company who want to work remotely. These roadblocks assume some level of forward motion. If you like working in the office, the factors outlined may not apply for you ;)
• This article is not trying to convince you to work remotely - I want to educate you as much as possible so you can make the right decision for you, your team, or your company.

Let's dive into the roadblocks to working remotely. I've tried to break them down by category - organizational roadblocks vs. personal roadblocks.

Company Roadblocks

1.) Existing Process & Risk

First up - many organizations have existing processes that were not built with a remote workforce in mind. The idea of distributed work is still a new concept, which means that there are many companies who have created processes that do not accomodate distributed teams.

For example - a company all-hands meeting. Perhaps the (un)structure of the all-hands meeting is where the CEO will babble for an hour, take a few questions from the audience, and employees promptly leave and forget everything that was discussed. Maybe this format has existed for years - why overturn the apple cart now?

Over time, a company will build a culture and way of operating that becomes deeply engrained. To simply say, "we want to work remotely, you should change your way of operating, the future is REMOTE" is a tough sell. It creates unknown risk and requires a lot of energy to reconfigure the operations.

Compare and contrast this to a company who is struggling to hire the talent they need in a certain constrained geography. There is a serious pain that exists, which may cause the company to change policies and standard operating procedures to allow the possibility of remote work arrangements.

Organizations respond to pain. If the pain isn't obvious, reconfiguring a process may not happen due to competing priorities and potential risk.

P.S. - as more companies are distributed from day one, this will become less of an issue in the future. 

2.) Lack of written artifacts & organization

Next up, many organizations do not have written documentation or standard operating procedures. This is can be true of distributed teams as well.

There's a lot of unspoken tribal knowledge that exists and can only be picked up by being in the office and observing behavior. I wrote more about this topic and consider written documentation to be the x-factor of a distributed team. If documentation doesn't exist, it will be very difficult to work remotely as no guardrails exist.

Many organizations will try to solve this problem with a wiki. This is a good start, but does not go far enough. A small number of employees will document processes (typically because several people ask them the same question over and over). Additionally, the schema of a wiki can be unstructured and confusing, so people will still ask where something is...even if it's in the wiki.

Once again, a wiki is a good start, but there's a need to go a step further.

3.) Manager's schedule vs. Maker's schedule

If you make stuff or produce a tangible good, having long stretches of uninterrupted time is critical to doing high-quality work. This is known as the maker's schedule. A couple meetings sprinkled throughout the day could destroy productivity, so working from home may be ideal for this schedule because it gives you time for deep work.

Unfortunately, there is another type of schedule that revolves around the coordination of the people doing the work - it's called the manager's schedule. As a leader of people, your output is measured by the output of your team and the adjacent teams you influence (Andy Grove talks about this in high output management). 

What's a common way to coordinate a team and understand what everyone is working on? Hold another meeting!

For many managers, a distributed team scattered across timezones can feel like a nightmare. How will you know what everyone is working on? The office provides clues, but working remotely does not.

I'd argue this is a major reason why you see some teams being able to work remotely, while others are required to be in the office. The manager holds the keys to distributed work arrangements, but wants to protect the way they operate and coordinate.

I find this to be one of the least compelling factors in this list - in fact, I think it should be challenged. If the output of your team is the measure of your success, you should dig deeper and create ways to make sure each person on your team is as productive as they can be.

4.) Difficulty Collaborating

Difficulty collaborating is a roadblock that I hear/observe when a team or company is considering remote work. The argument is that being co-located creates an environment where it is easier for people to work on ambiguous problems because they are all in the same room.

Think of this as the classic white-boarding session, where a people are brainstorming and scribbling notes. Creative sparks are flying. This is the moment where genius arrives!

Quite frankly, there is some truth to this point. I worked remotely for three years for one company and found spending time in the office to be helpful, especially when exploring thorny problems with coworkers.

One of my favorite communication frameworks is called media richness theory and is based around the idea that certain communication mediums (i.e. - written, telephone, in-person channels) are more beneficial than others if you are trying to reduce uncertainty or ambiguity. Here's a cool graph to illustrate.

Keep in mind that this is a theory and there's plenty of people who have different opinions. I take this theory with a grain of salt.

What I find interesting is that very few distributed companies will argue with you about the benefits of meeting up in-person.

The question is, "how frequently does this need to happen?"

A common practice of a functional distributed team is to hold a company retreat, with a special focus on brainstorming, white-boarding, and discussion of ambiguous concepts like company strategy or values. It's also a great chance to get to know your coworkers, which we will discuss shortly.

5.) Dogs, Beaches, and Nomad Culture

This next point may be controversial, but as I read articles on working remotely, they feel like multi-level marketing schemes or stories that are too good to be true. For example, watch this video (please notice the mastermind link in the description, which perfectly illustrates my point)

It's hard to watch this video. The content may be good, but I was too busy mumbling about the fact that this person is walking around in some random beachside town.It doesn't feel serious.If your boss who doesn't like remote work spends about five minutes Googling and finds this, it will be a major turnoff. What sane boss will let their employee waltz around sipping fruity drinks on the beach while they work?

I want to be clear - working remotely provides numerous benefits, many of which are documented in videos like this. BUT, it also feeds into the belief that when someone is working from home, they aren't working.

I guess what I'm saying is that if you work remotely, please act professional. It's okay to travel. It's okay to have your cat sit on your lap for a few minutes at work, but it's also important to act like adults with this newfound responsibility.

6.) Existing Software and Tools

A lot of progress has been made with Slack, Zoom, and Microsoft Teams over the past few years, but there's still more work to do here. I believe there's still whitespace and in-office behaviors that can/will be shifted to a digital environment. The massive rise in the presence of apps to help with company work is helping to make remote work a breeze.

Believe it or not, many companies adopt technology very slowly. For example - my sister works at a civil engineering firm that still uses email for internal communication. The noise of Outlook notifications all day would drive me nuts. They recently started using Microsoft Teams and it's already making the possibility of remote work more likely.

Other organizations still don't have a video conferencing options. This will change with time.

Now let's talk about personal roadblocks to working remotely.

Personal Roadblocks

1.) Water Cooler Discussion

The next roadblock to the rise of remote work revolves around the notion of water cooler discussion (or the lack thereof as a remote worker). Once again, this is a legitimate point that should be taken seriously - but not literally. I don't know of people who relish trips to the water cooler. Is the office water special?

Instead, the underlying theme is that people want to get to know their coworkers and build a better relationship with them.

The office environment creates an environment where it's easy to learn more about the people that you work with, like how they prefer to work, their personality, and what they might enjoy doing outside of work. This information tends to be collected through observation and interaction like:

• Grabbing lunch or coffee with a coworker.
• Interacting in the hallway before/after a meeting.
• Seeing random tidbits about someone, like a photo of their family on their desk, which sparks discussion about family/hobbies/etc.

I have experienced this pain as a remote worker. There are times when the people you work with feel like words on a screen. That's it. While I don't think you need to become best friends with someone at work, having a better understanding of the people that you work with helps humanize work, which can make the experience more enjoyable, especially if you are extroverted.

Once again, there are ways to mitigate this as a distributed team. In a future post, I'll outline ways to humanize distributed work. It's an area that needs a lot of improvement I think.

2.) Social Isolation

Another personal roadblock to working remotely is that people can get cabin fever and become lonely. As an extrovert, I enjoy being around people and become energized by human interaction. When working from home, there's a gravitational pull to stay at home. For many, the concept of working alone sounds like a nightmare. For others, it's a dream.

I won't opine on this point, because it depends largely on your personal scenario, but I've found numerous ways to mitigate the feeling of loneliness. For example, I make a point to meet with a 1-2 people for coffee every week. I'll add more color in a future article.

3.) Blurred lines between personal life & work

Another challenge and roadblock to working remotely is that the lines between personal life and work can become blurred. I see two major contributors:

• Your coworkers are in different timezones. A coworker might be hard at work when you are having dinner.
• You are a short walk from your "office." Where you work is the same place as where you live.

Coworkers in different timezones is a tough nut to crack. It may be critical to collaborate with a coworker in another timezone, which creates an inconvenience for at least one person. This coordination cost and the effort required can be a detractor to distributed work.

In Conclusion

I hope this piece was helpful and provided some clarity. I believe that many of these roadblocks can be overcome with effort, but understanding and diagnosing them is the first step.

Once again, remote work may be ideal for you, but not ideal for others. If you'd like to stay in the loop, I'm writing a book on distributed work which I will probably give away.