Why Remote Workers Fail

[On Tuesdays I write about the top voted question on Ask Berkun (see the archive). This week’s question is from Regina [330 votes]: What gaps in communication exist in global virtual teams? Which I have simplified for your reading pleasure to why remote workers fail.]

The best argument about the viability of remote work is that it’s about results: any boss should let their good employees work remotely on a trial basis and see how it goes. If they can perform just as well, and their coworkers have no complaints, what’s the problem? You lose nothing and have a happier employee. Sadly many managers are afraid to try new ideas of any kind, which suggests they’re not all that great at being the boss anyway, but that’s a topic for another post.

Even when a remote experiment is done, and it fails, often it’s the remote worker, or the very idea of remote work, that gets scapegoated. This is sad. It’s far wiser to start by blaming the manager instead. Why? Well the Leffert’s Law of Management states that the starting assumption for managers should be that whatever is going wrong is their fault, and this rule applies to remote work too. A good boss realizes it’s their job to create an environment their staff can perform well in and remote work is just another scenario they should be taking responsibility for.

This sets the stage for the five most common reasons why remote workers fail:

  1. No ally in the main office. If there is a primary physical office, it’s hard for remote workers to know what they’re missing. Someone has to look out on their behalf in meetings, hallway discussions or post work happy-hour chats. No one likes having their time wasted, but without an ally decisions are often made that are not communicated to remote workers, even when those decisions directly impact them. It’s not hard to learn the habits of being an ally, but someone has to lead the way. Some workplaces adopt a remote-first culturewhere as many discussions, meetings and processes are done online, and with tools that can be used from anywhere and at anytime (which often benefits “non-remote” workers too, as all conversations are archived and searchable, people can be more productive when traveling, etc.). The boss is the most obvious ally for a remote worker, making sure their perspective and needs are represented.
  2. Cultural bias towards caution. Amazon and other companies talk about bias towards action as a key part of their culture. This means the default posture every employee is expected to have is to be aggressive in making decisions and taking action, rather than waiting to be told what to do or taking endless precautions before acting. Remote workers are more likely to do well in these cultures, as their autonomy becomes an advantage, rather than a source of frustration. Bias towards action also tends to create more resilient employees who are comfortable identifying and solving problems (including perhaps diagnosing co-ordination frustrations involving remote workers). The more overhead and coordination required by a culture, the more pressure that’s put on remote communication tools and the team’s ability to communicate well (see #4).
  3. Poorly defined role. Remote workers benefit from clearly defined roles where they have more freedom to decide on their own how best to use their time and resources. Even if their role requires high collaboration with other people, explicitly stating what’s expected, what powers they have and how their performance will be measured is essential to their success. Of course poorly defined roles are a problem in any organization, but the negative impact is amplified with remote workers. A role likely needs to be reevaluated, and possibly modified, when it’s transitioned to a remote position.
  4. Poor culture of communication. When you work remotely you depend heavily on written communication: email, chat rooms, and more. Organizations that have cultivated excellent communication skills make it much easier for people to work remotely, as it’s built into the culture to ask clarifying questions, to be helpful to coworkers and to document processes and decisions in a way that other people can easily comprehend. One of the great discoveries I made when I worked for WordPress.com (Automattic Inc. is 100% remote) was how thoughtfully everyone wrote and read, and at every level of the organization. It’s taken for granted that most organizations in the world consistently hire people with good communication skills, but in reality good/mature communication skills are uncommon, and the price paid for poor communicators is amplified for remote workers.
  5. The wrong person was hired. Hiring good people is hard enough, but to hire someone for remote work demands extra care. Remote work isn’t for everyone. Some people depend on the energy they get from being physically near their coworkers, or the psychological value of going to a physical place to “do work” and leaving to go home. Remote workers often need above average organization skills and self-awareness of their working habits. Being proactive as a remote worker is a major asset, as even in an organization with allies and a bias towards action, remote workers by definition must take more responsibility for themselves than other employees do. Automattic wisely hires by remote trial, which makes a candidate’s remote working skills part of how they are evaluated.

Despite the suggestion of the image shown below, it’s uncommon for remote workers to fail because they abused their privileges. Many people who choose to work remotely greatly appreciate not having to commute in traffic, value the ability to easily take care of their family (if they work from home) and the superior control they have over their lifestyle when compared to more conventional employment. It’s for these reasons I advocate workplaces give it a try and for people to ask for it. There’s much to gain and little to lose.

Have you seen other reasons why remote workers fail? Have a theory? Leave a comment.


10 Responses to “Why Remote Workers Fail”

  1. John Armitage

    Thanks for this Scott.

    One could say that your five ways for remote workers to fail might also be the five ways that any worker fails.

    Would these five ways be different for an on-site worker? If so, how?

    One (timely) thing that comes to mind about working remotely is a reduced risk of workplace discrimination/harassment based on the worker’s personal attributes.

    The question begged here is that, somewhere on the list of how to fail in your job is to resist unwanted sexual advances by those more powerful. Then again, the long reach of digital image attachments and humiliating speech can still come home….

    1. Scott Berkun

      Good question! Not sure I’d change much – which I suppose supports the central point I was trying to make. It’s really just another kind of employee.

      When I wrote the book I had the same hypothesis about diversity – but in all hinges on hiring. Even if remote work does have that effect, unless the hiring is done remotely too the same biases end up in the culture.

      1. John Armitage


        I was thinking less of the hiring bias than the unsound temptations arising from time spent in close quarters.

  2. Fendy

    This post makes me think, if remote working fails at the end, what are the managers doing all that time? Do they do not track progress, problems, questions, and in the end just blaming the workers for remote working?

    Even though it’s remote, the progress must be tracked everytime and any hindrance or problems need to be addressed asap.

    1. Brian

      You’re right. However, I’d go as far as to say that remote work probably removes a whole ton of bias that occurs from factors in being together in the same physical environment (desk-hours, physical attractiveness, etc. etc.) and instead help managers focus more on the results.

      I guess the problem being addressed arises more in a mixed environment.

  3. Frank

    Thanks for this Scott. I had experienced in hiring the wrong person

  4. Paul Kent

    Great piece. The advantages of remoteness are outweighed by the drawbacks of watercooler decisions and the nurturing of workplace advocates. That said, a combined approach of in and out of office working can give the best of both worlds. I have found that i can segment my work based on where i am. At home i can be organised and focussed on task, in the office i can focus more on face to face.

  5. Pawel

    I’m remote worker since 5 years now and I would never go back to the office. Simply because I can focus at home, I can actually do my job there, and most important, I do not waist my time for traveling to and from the office every single day.
    From the other hand, every time when I’m at the office (one week per 3 months), I cannot focus at all. Everyone is asking me for a coffee, meetings, other questions. I think it’s safe to say that my 8 hours at the office are like 3 hours at home. And I think if you don’t know how to manage your employees and monitor their tasks, then it does not matter where they are.
    Few tips for having remove workers: use jira, slack, git, and other online channels for communication. DO NOT discuss anything at the office while others are at home, instead just move every discussion to the jira or slack so everyone will be aware what’s going on. Hire good managers.

  6. Michael LaRocca, Business Editor

    It seems to me that if you don’t trust an employee to work remotely, you probably don’t trust them in the office either. I like how this article starts with a basic “try it and see what happens” attitude. Remote workers probably fail for the same reasons that all workers fail. Either you hired the wrong worker, or you didn’t train them, or you’ve got bad management.


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