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Updated January 14, 2025You’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.
“To remain productive, effective remote workers need to be able to give themselves structure without the crutch of a standard office environment.”—Greg Caplan, CEO, Remote Year*
The characteristics of people who will thrive as remote workers mirror the practices of successful remote teams that we laid out earlier (and we cover in more detail in Being a Successful Remote Worker). You’re looking for candidates that are:
Clear and frequent communicators. Written, asynchronous communication is a cornerstone of successful remote teams. While you can teach this, depending on the size and makeup of your team, you may not want to dedicate time to building this from the ground up in a new employee.
Intrinsically motivated/self-disciplined. While this is a positive characteristic in any employee, it’s table stakes for someone on a remote team. They won’t require the external structure of a physical office, and can autonomously manage their time productively.
Capable of taking initiative. With clear goals, a remote member of your team will be able to get the necessary work done without needing to regularly check in, and are capable of unblocking themself.
Comfortable with longer periods of solitude. Many remote workers seek this out, but someone new to this style of working may be surprised by its impact on their mental health.
When assessing someone’s ability to work remotely, they don’t need to have remote experience per se. You can look for proxies of remote success by screening for specific attributes. Some common ways these can manifest are:
A nontraditional background
Previous roles that required a lot of autonomy
Unusual or uncommon skills
These things tell you that the candidate didn’t have a path laid out for them to simply follow; they needed to take a lot of agency in figuring out their path. This level of agency correlates well with remote work success. (There’s nothing wrong with a traditional in-office background; it just doesn’t provide any insight on this specific point.)
If a candidate has worked remotely, it’s much easier to ask them about their specific experience and determine whether they’ll succeed. If they have not, you can ask them about what challenges they expect, and what adjustments they plan to make. You’re looking for thoughtful, specific answers. Successful remote workers tend to be self-structuring people who prefer to make plans and stick to them.
cautionIf candidates are blasé about the unstructured elements of remote work and have no experience with it, they might not have the skills to create their own structures and routines; or, worse, they might have no idea what they’re getting into. You’ll want to probe more for how they might handle these challenges.
Another tack is to ask candidates questions about how they like to work when they’re happiest during the workday, and about times they’ve felt especially fulfilled or frustrated at work. It’s important to listen carefully for whether you can provide that. Long stretches of quiet time, alone in a room with music? Remote work might be a good fit. Lots of team whiteboarding and brainstorming over lunch or a happy hour? This person might suffer in a remote team. Do they get frustrated when they’re alone with a difficult challenge (and so will struggle when they get blocked in a remote role), or do they prefer the chance to mull over problems independently? Do they get most frustrated when a colleague interrupts their focused work with a question, or when they have nobody around to collaborate with?
importantOf course, your team structure will make a difference here. Some remote teams do a lot of collaborative work, and others are more asynchronous. Some are essentially teams of one, with each person working on a discrete project, and others are very collective. It’s likely that the work will require a combination of autonomous focus and decision-making, and collaboration. So someone who has the self-discipline, focus and initiative to succeed in a remote environment, but prefers a more collaborative work style, might be very happy in a remote team where teamwork and collaboration happen daily.
When you’re discussing your team, it’s always best to be very upfront about what it will be like, and what kind of challenges someone might experience. For example, if your team is chaotic and communication is haphazard, you would candidly share this. Some people might respond gleefully that they thrive in chaos and enjoy the problem-solving that chaos necessitates. Others might be visibly put off, or even withdraw. Or you might be looking for people who will help make your system more streamlined, and some candidates may be excited by that challenge, while others will be looking for a company that already has a sophisticated remote communication structure. The additional reason to do this is that you’ll want people to know what working at your company is really like, so that if they know they won’t succeed there, they will filter themselves out. The alternative is replacing them and hiring again for that role in a few months. In sum, to help candidates reflect on what will make them happy and successful, it pays to be honest, explain your motives in sharing challenges, and that you’re truly seeking to understand whether they will enjoy the environment. This includes clarifying that it’s not a test and there’s no hidden agenda; you both want to find a situation that works for everyone.
If a candidate will be remote, it’s important to assess how they come across in the context of your remote team. You’ll want to create a hiring experience that in some ways mirrors how the candidate will end up working, to test whether the candidate will succeed in the remote environment. For example, if the position you’re hiring for calls for mainly written communication, some video discussion, and a lot of audio-only calls (for example, conference calls), then it’s important to get an idea of how successfully they use these communication mediums. Hiring based on a phone screen and an in-person interview for this role wouldn’t be a realistic measure of their on-the-job performance. Instead, we recommend that at least some part of the process be done online, via video chat and, ideally, using written communication as well.
importantIf your company has co-located employees as well, it’s important to use the same methods to interview candidates who won’t be remote. They’ll have to be working using the same mediums as remote employees, and will be communicating more asynchronously and in writing as well, so you wouldn’t want to presume they’ll need a different skill set.
An onsite-only interview process can obscure communication issues, because some candidates will compensate for their weaker verbal and written communication with effective body language. Body language—nonverbal communication competence—directly affects communication: research shows that people are judged as competent based on factors like what clothes they wear and how confident they appear.*
Nonverbal communication competence is a person’s ability to transmit or interpret information via nonverbal communication, such as clothing, body position, gestures, and facial expressions.*
cautionThe risk with an onsite or in-person only hiring process for remote workers is that you hire someone who comes across as a strong communicator on the basis of their body language and appearance, rather than the content of their communication. In this scenario, the new employee then fails in the remote context, because they can’t use the body-language skills that they rely on to communicate, and their written and verbal communication—which didn’t get assessed—turns out to be inadequate.
To avoid this trap, you’d need to assess how well the candidate performs without those extra body language signals by evaluating their verbal and written communication abilities, which are the main avenues of communication available to remote workers.
For assessing written communication skills, a written assignment can be helpful. This can take a number of forms:
A sample email. Ask the candidate to describe their expected work progress for a small task, as well as its outcome.
Take-home assignments. These could include a documentation component like a coding assignment that includes writing (like creating a README file and instructions), or a plan for getting user feedback on a new feature.
A text-based interview. Have the candidate and interviewer communicate over instant message chat instead of phone or video. Automattic, a fully remote company of several hundred, interviews over text-based chat only.
It’s important to look for clarity and tone in written communications: the most common failure modes are rambling, unclear writing that will make working with the person a drag, and tone that reads as negative or unprofessional. Tone is notoriously hard to convey in text, and teaching this skill is possible, but arduous. It’s critical not to underestimate the value of a candidate who is able to come across as positive and professional in a written context.
In order to assess verbal communication, a paired interview over a video call can be helpful.
In a pair video interview, two interviewers simultaneously assess a single candidate. Typically, one interviewer leads the interview while the other observes. Microsoft’s Developer Division and Twitter, among others, use pair interviewing exclusively.
A pair video interview allows you to re-create a small-group meeting dynamic. This setting allows one person to observe more closely and take notes while the other interviewer asks and answers questions. It gives a second perspective on answers, so you can compare notes. This means that subtleties in how the candidate communicates and performs in the remote interview are more likely to be noticed.
For example, did the candidate consistently refer to a hypothetical software engineer as “he”? This can be an English as a Second Language dynamic, but it can also indicate an inclusion problem you need to dig into. Did they answer very differently when asked questions by one interviewer compared to the other? This can indicate that they’re not equally comfortable or competent communicating well with different people.
Other common examples are engineering candidates treating more technical interviewers differently from those who may be less technical. Conversely, a strong candidate in this situation will not assume they should only talk to the more technical person, and will purposely aim their answer at the appropriate depth for both. You will want to note whether the candidate changes the way they communicate when the interviewers present different genders, races, ethnicities, or other statuses; are at different organizational levels; or have different roles.
controversyA common attitude when hiring remote roles is that it’s not possible to have these positions filled by less experienced junior candidates. The tenet that remote work only works for highly experienced, senior hires does have some truth, but isn’t the full picture.
When companies say things like “it’s basically impossible to have a junior remote worker,” what they often mean is “a remote worker who lacks strong communication skills and professional skills like goal setting and independent action will fail.” And to some extent, that’s true. Junior hires often lack necessary professional skills because they tend to be younger. However, this is correlation, not causation. The simple act of being more junior doesn’t by itself imply lower professional and communication skills. In some cases, it can be the opposite: career changers, for example, often bring highly developed professional skills, even though their specific experience is low.