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Updated March 23, 2023You’re reading an excerpt of The Holloway Guide to Remote Work, a book by Katie Wilde, Juan Pablo Buriticá, and over 50 other contributors. It is the most comprehensive resource on building, managing, and adapting to working with distributed teams. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, 800 links and references, a library of tools for remote-friendly work, commentary and future updates, and a high-quality PDF download.
Attitudes about remote work are changing rapidly as more companies choose to embrace it. But there’s still a lot of fear, uncertainty, and doubt (FUD). Remote work is neither universally good nor bad, but is rather a series of ongoing tradeoffs and adaptations to a company’s approach. Here we dispel a few (positive and negative) myths and call out common pitfalls that companies and employees can avoid along the way.
Today, only 30% of remote-friendly companies are all-remote.* Despite a degree of punditry on this topic, especially from early-stage startups, remote-first or all-remote companies aren’t guaranteed to be “doing remote” better. Remote is very rarely all or nothing. Almost every company is a hybrid and each person or team is on a continuum of on-site to fully remote.
The vast majority of companies are going to have to ease into supporting remote work and intentionally design the right culture, processes, and systems to support it. What matters is that they consciously examine what will work for them, and plan to revisit that as their company grows and plans change. There are a few common pitfalls to look out for as this happens.
cautionWhen no one in management or a leadership position is remote—as often happens in many hybrid remote companies—you’re more likely to be missing key pain points or cultural problems for remote workers. You’re also more likely, (although not guaranteed) to have a system where decisions are made centrally and remote employees feel they are “out of sight, out of mind,” and left out of what’s happening in the office.
cautionThe corollary pitfall when everyone isn’t remote is treating remote work as a privilege. Remote work is sometimes offered as a perk or gift to more highly valued or tenured employees, and not offered equally for everyone. It is important not to treat remote work as a privilege, but instead to understand that it is a two-way, mutually beneficial relationship that both sides continually invest in.
It’s worth noting that plenty of people simply prefer to work in an office. They may thrive on social connection, and be more energized working face-to-face with their colleagues. They may appreciate an emphasis on collaboration over autonomy, or freewheeling discussion over planned agenda meetings. Whether or not someone prefers an office environment or a remote one is often couched in terms of extroverts vs. introverts, but it’s more complicated than that. In reality, the likelihood of a person’s success in and happiness with one environment or another is influenced by a variety of personality and work style factors. For example, those who prefer not to work remotely can express concerns about isolation, distractions at home, or a dislike or discomfort with video conferencing.
importantHow sophisticated a company’s remote policies are can influence whether someone who considers themselves an extrovert would actually thrive in a remote setting. But remote work is not for everyone, and no amount of evangelizing can change someone’s mind when they just want to be around other people.
cautionAn ironic corollary to the myth that you can hire people anywhere is that if you don’t have a hybrid model with an office people can work from, you might also be missing out on talented employees who much prefer an office environment over working from home.
Not everyone is compatible with remote and that’s okay. We’ve had numerous people over the years quit HashiCorp saying ‘loved the work, loved the people, but I just need in-person social interaction.’ That’s totally normal.Mitchell Hashimoto, co-founder and CTO, HashiCorp*
When companies or managers say this, what they really mean is, “When people are in the office, I think I know when they’re working.” But presence doesn’t guarantee productivity, and it certainly doesn’t mean employees have clarity about what they should be working on. As we discuss in Key Channels and Tools for Remote Communication, the practices of clearly setting team goals and establishing more asynchronous channels of communication allow remote teams to thrive without constant managerial oversight.
cautionInstalling monitoring software will not help your company know for sure if people are working instead of slacking off. In fact, it will erode trust, which is the backbone of a healthy remote team.* A properly aligned remote team with clear goals and autonomy won’t require tracking. (See more in Managing Distributed Teams and Remote Company Culture.)
This is true in principle, but complicated and not always possible in practice. Hiring outside your home base, especially once you start hiring internationally, raises a whole host of legal, financial, and operational concerns that may constrain how aggressively you pursue this. Additionally, managing time zones turns out to be one of the more thorny problems that remote companies face, which may also impact how you choose to approach hiring from afar.
There’s a grain of truth to this concern about remote work, but only if your company doesn’t intentionally design how it will support remote workers. The way co-located teams collaborate doesn’t translate to a distributed model. Teams can’t rely on being in the same space to get context, share ideas, give and receive feedback, and iterate or brainstorm. The nature (and, sometimes, timeframe) of collaboration shifts when people move outside an office. But it’s not necessarily ineffective. Remote collaboration requires rethinking how remote teams work together, and also designing practices to support more asynchronous progress while still helping team members trust and learn from each other. (See more in Remote Collaboration Ground Rules.)
Much like workplace communication norms, company culture has been heavily shaped by physical presence. Proximity has long been a proxy for what constitutes culture, despite not being the primary factor that establishes any given culture, nor a guarantee that a culture will be healthy. The belief that remote teams won’t have a cohesive culture is the same belief that maintains that co-located companies have good cultures to begin with. As we cover in Remote Company Culture, shared values—and the specific practices of communicating and promoting those values—largely shape a group’s culture whether group members are co-located or not. Values can and should be written down, shared liberally and regularly, and revisited as a company grows and changes. Like many other written, asynchronous practices, values—and the culture built from them—can survive, and even thrive, in remote settings.
importantWe don’t intend to downplay the difficulties involved with establishing and scaling a healthy remote culture. But like any other aspects of remote work, it’s a matter of doing the work. And most importantly, it’s a matter of realizing that culture isn’t a set-it-and-forget-it phenomenon. Darren Murph, Head of Remote at GitLab—arguably the fastest-growing all-remote startup out there—acknowledges the work required to maintain their culture:
It’s a daily, intentional challenge. I’m working a lot on onboarding right now. One of our biggest risks is “losing the values that bind us.” When we have too many new people coming in too fast, they are figuring out where they fit in. If you’re not careful, they don’t realize they have permission to do things differently. If too many of those people come in and “talk louder” than others, then the culture starts to tip in that direction. Any leader who appreciates the culture they’ve built has to continually watch out for that. Your natural inclination is to get them in and working quickly, so you don’t have the time to teach them to do things differently. The thing that GitLab has going for it is that stuff that we let people leave behind is what people usually want to leave behind. It’s like hiring a new soccer coach, someone who views the field the way the old coach taught them. If you take that person and then add a flood of new players, it’s hard for the existing players to teach them their playbook.*
Digital nomads can and do thrive in some cases, but traveling consistently consumes more time, money, and energy than staying in place, and many remote companies still are not willing or organized enough to support nomadism for one or more employees. The unique demands of digital nomads (along with other remote work factors like isolation and lack of social support) are some of the inspirations for organizations like Remote Year, which puts digital nomads into cohorts and provides logistical and on-site support for people traveling and working remotely.
contributeWe aren’t covering digital nomads in this Guide, but we’d love to hear more from people working this way to help us inform potential future updates.
60% of remote workers still work a fixed-schedule job five days a week, involving meetings, video calls, and plenty of collaborative work. It’s likely that this schedule correlates with the majority of remote companies still being hybrid, which could constrain remote team members to more traditional in-office schedules. But even if your schedule is not a traditional 9-to-5 routine, that doesn’t mean you truly get to do whatever you want, whenever you choose.
caution In some remote teams, handling time zone differences can mean occasional odd hours for meetings. Distributed teams often work across time zones, and you’ll be collaborating with people on the other side of the country or the world. We’ve provided ways to manage that later, but differing time zones can be either a benefit or a drawback. Managed well, time differences let you get stuff done in your working day with fewer interruptions; but managed badly, they can lead to long lead times, misunderstandings, or meetings at undesirable hours—and can even exacerbate feelings of isolation and loneliness.
Despite favoring remote work over an office environment for reducing distractions, many people who work remotely end up managing a whole set of surprising new distractions. Barking dogs, construction next door, family or friends wanting to visit, door-to-door salespeople—they can be just as frustrating or disruptive as colleagues tapping you on the shoulder, especially when you’re on a video call with a group of people. A few consistent examples include:
Family and friends. It’s important to set strong boundaries on your availability with your loved ones—just because you’re working from home doesn’t mean they can turn up any time for coffee, or treat you as an emergency babysitter. Having a separate office space where you live helps significantly with this, though we realize that’s not always possible. That said, getting the balance right with friends and family can be excellent for your mental health. As with any other possible work distractions, balance is what really matters.
Digital distractions. While these are an issue for office workers as well, digital distractions (social media, e-mail, IMs, et cetera) can be particularly tempting when you’re on your own and don’t have as much built-in social interaction as you would in an office. We’re big fans of Cal Newport’s Deep Work, which helps people set aside distractions and get into a flow-based focus mode. The Society for Human Resources Management (SHRM) also has a set of helpful tips for managing your digital appetite, and Zapier lists a few apps you can try as well.
Environmental distractions. That pile of laundry in the next room, a sink full of dishes, weeds popping up everywhere outside—home offices are full of unique ways to get off-track and waste time. The sections on Time management and Productivity have concrete suggestions for managing your time, while still giving yourself space to take some breaks and knock out a few chores or the like.
I have a dedicated office, which cuts down on a lot of distractions. I know that when I go into my office, there’s nothing to do but work! If I’m feeling really distracted, I’ll give in to that. If there’s something on my mind, like an urgent errand I know I need to run or a huge pile of laundry that needs to be folded, I’ll take a break and take care of whatever needs to be done. I’ve found that if I try to work while I’m distracted, I usually end up getting very little actually done. It’s better to just address it head on and then come back to my computer feeling more relaxed.Jenn Leaver, Senior Manager of Product Documentation, GitHub*
In a healthy remote company, there is no “out of sight, out of mind.” Remote teams have to have high levels of trust, and individuals need to be able to work autonomously without constant oversight. But that doesn’t mean there’s no accountability. Most remote workers still have clear reporting structures, goals, meetings, and so on. (In fact, many companies unintentionally overcompensate for the lack of in-person interaction and end up having far too many video-call meetings.)
cautionRemote work makes it harder to communicate and collaborate with the rest of the team, with 20% of respondents of remote workers saying it’s their most important issue.* Whether or not your company addresses this problem with more meetings or more emphasis on asynchronous communication depends heavily on your company’s philosophy and communication practices. If fewer meetings are the default, be prepared to trade off that time for more writing and documentation. Although managers and supervisors have a part to play in cross-team communication and collaboration, it also requires individuals to take the initiative.
The negative corollary to the benefit of working from home and having more time and flexibility is that work and home are more entwined. Many remote workers report difficulty detaching and stopping work at the end of the day. When you work from home, it’s easy for work and personal time to blend together, and many remote workers report working longer than if they were in an office—up to 43% more.
cautionIt’s not as easy for remote employees to maintain strong social connections with work colleagues, which can cause feelings of isolation. Distribute Consulting notes that isolation isn’t necessarily about being physically isolated:
We find that remote work isolation is more informational than it is social. Meaning, workers don’t miss sitting next to someone; they miss having access to someone. They miss being able to spontaneously ask a colleague a question, or celebrate a small victory, or brainstorm a solution or a problem, or even just chatting about weekend plans. If remote workers are craving some daily physical interaction, that’s where social hobbies, coworking spaces, and dedicated relationships with friends and family can be utilized.
Avoiding loneliness (or dealing with it when it does crop up) requires a proactive approach—you need to take the time to connect with colleagues, friends, and others, and to protect your mental health. More importantly companies must do their part to encourage healthy behavior, through both values and policy.
This section was written by Steph Smith.
Remote forces you to do the things that you should be doing anyway, earlier and better.Sid Sijbrandij, co-founder and CEO, GitLab*
From the outside, a successful remote team looks like a successful team. They hit their goals without burning people out; team members understand what they should be working on and feel ownership and pride in their work; they have open and honest communication and can positively resolve conflict; they are resilient and can adapt to failure and change.