Hiring Remote Employees

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Beyond cost savings, easier access to talented employees is one of the biggest reasons employers consider supporting remote work. Especially for startups and high-growth companies, the talent supply is limited and in high demand, making hiring very competitive, especially for technical roles. Being able to hire outside traditional tech hubs like the San Francisco Bay Area or greater New York City means people can find the talent they want almost anywhere in the world.* Even in less competitive industries, advances in technology make remote work feasible in many roles, granting those employers access to a much broader and more specialized workforce.

A lot of hiring best practices are similar across in-office and remote roles—for example, clarity about the role, sourcing a high-quality applicant pool, and being explicit about cultural values. These practices become even more important when hiring for remote roles. Candidates will be working in physically isolated locales, so small issues can be magnified. We won’t cover all the ins-and-outs of standard good hiring practices, which you can find in our Guide to Technical Recruiting and Hiring as a companion to this section.

Remote Job Postings

Along with all the key elements of a good job description, a remote role position announcement will need to include the following additional information:

• Clarity around geography. As we’ve already seen, there is no single flavor of remote. You will want to make clear in the description whether the role is fully remote, whether there’s an office they can/will need to go to occasionally, and any other details (for example, “U.S. remote only” or “time zone agnostic”).

• How remote works at your company. Strong remote job descriptions clarify the values and practices around distributed work. They make clear that skills like communication and collaboration are required. This is your chance both to sell applicants on the premise of the role and to make clear how you expect them to work with the rest of the team.

• Specific keywords. People searching for remote jobs are more likely to find you if you include terms that applicants are likely to search for:

  • Remote

  • Distributed

  • Work at home

  • Work from home

  • Work from anywhere

​important​In the title of the job post title, it’s best practice to list “Remote—(geographic region)” in the location field of the job posting. For example, where a non-remote job posting might advertise “QA Analyst, Atlanta GA,” the remote version would be “QA Analyst, Remote within the USA,” “QA Analyst, Remote within Eastern Standard Time,” or “QA Analyst, Remote (global).” The geographic region indicates where the employee would be located, not where an office location might be.

In the case where a role could be either in-office or remote, some companies have two separate listings. Many candidates who prefer in-office work won’t reply to a remote position, and of course, candidates who aren’t in that location won’t apply unless the remote option is obvious.

Having separate listings for the remote version of a position also allows you to tailor the job requirements to include the different skills that a remote position demands, and for you—the employer—to customize perks and benefits (for example, instead of “catered lunch,” perhaps you offer a lunch stipend).

Assessing Remote Candidates

Attributes of Successful Remote Workers

“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.

Assessing Ability to Work Remotely

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.)

Key Questions to Ask

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.

​caution​If 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?

​important​Of 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.

Interview Via Video, Audio, and Text

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.

​important​If 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.*

​caution​The 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.

Hiring Junior Remote Employees

​controversy​A 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.

Professional Skills vs. Seniority

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.

For now, let’s restrict the discussion to junior staff who also have strong professional and communication skills, presuming this is what you’ll screen for. In this context, it helps to clarify what “junior” means. A helpful concept is task-relevant maturity.

Task-relevant maturity (or TRM) is an employee’s experience level for a given task, reflecting a combination of how achievement-oriented they are, their readiness to take responsibility, along with their education, training, and experience. Andy Grove popularized the term TRM in his book High Output Management.

Grove noted that the amount you train and monitor someone depends on their TRM, and should change as they learn and their TRM increases:

How often you monitor should not be based on what you believe your subordinate can do in general, but on [their] experience with a specific task and [their] prior performance with it—[their] task-relevant maturity… As [their] work improves over time, you should respond with a corresponding reduction in the intensity of the monitoring.*

Someone who is “junior” has low task-relevant maturity in most of the key competencies for their role, meaning that most of their activities need to be monitored as they are being actively trained. Someone who is “senior” in this sense has relatively few areas of low TRM, and thus rarely needs monitoring or training.

​important​When people say it’s impossible to hire junior people to remote roles, the underlying truth may be that the company hasn’t set up the necessary tools and documentation to help people thrive in a remote environment. Whether a junior person can be remote or not is really a question about whether the organization has the capability to provide monitoring and training to someone during the majority of their work tasks. If the company can’t do that, there are likely to be other problems down the road for their remote staff, no matter their experience.

The Burden of Training Is Higher

Monitoring and training a junior employee will be harder in a remote context. When you can’t look over at what they’re doing and offer help, there must be a system in place for them to know what they should be working on, but also to ask questions—or their manager will need to regularly check in on them. This consistent communication is a bit more challenging when it needs to be done via chat message and video call: managers can’t just say, “How’s it going today?” as they walk past the new employee to get a cup of coffee, and they can’t glance over and see whether they look frustrated or confused.

These challenges can be overcome by making sure the junior hire is comfortable asking lots of questions, and knows where to ask them (in email, in a call, in a Slack channel?); that they have access to company manuals and handbooks; and by pairing them with a kind and genuinely interested mentor or peer. If your company doesn’t have these kinds of communication paths and documentation set up, it won’t just be the new junior person who suffers.

Figure: Employee TRM and Company Structure

Source: Holloway

Here, consider your environment overall. Is it low or highly structured? Remote workplaces will tend to skew toward being low-structure workplaces, but they don’t have to be. It’s completely possible to be a structured, remote workplace.

If you’re remote, you’re by default less structured. You can change this default if you want to. If you care about hiring and developing junior (low-TRM) staff, you may need to impose structures for them to do well. If you remain low structured and you hire low-TRM employees, you increase the chances that they will fail. This is not because you’re remote per se, but rather is because you didn’t provide the structure that a low-TRM person needs to learn and succeed.

If you’re unwilling to make your environment more structured, then hiring senior (high-TRM) staff and letting them figure it out probably works better. Conversely, if you keep your senior (high-TRM) employees too constrained by structures optimized for junior folks, beware of bored people leaving for a role with less structure and more freedom.

​important​The point here is that the level of structure a workplace provides should best be tailored to the remote worker’s role; if your organization is willing to adapt its structures, you will be able to hire successfully at any level of seniority.

Doist overcame some of these challenges by sending new employees to the same location as their onboarding mentor, to spend two weeks working with them in person. This can be a worthwhile investment to get new employees onboarded quickly and to ensure they have all the context and cultural understanding to be productive when they return home. It’s also worth noting that an exhaustive handbook with timezone-agnostic detail for onboarding new people is critical when spanning large temporal gaps.

Can You Support a Junior Remote Worker?

When evaluating whether you can support a junior remote worker, consider how will you provide the monitoring and regular support that someone with low TRM in most of their job functions will need.

There are certainly ways to do this remotely. Being willing to invest the time of a dedicated mentor and a skilled manager will go a long way here, though some roles may be more difficult to train than others. Here are a few things to consider as you evaluate supporting junior team members:

• Can you get a meaningful sense of their work output remotely? For a job like writing code, the answer is likely yes. It’s feasible to read the code and run it yourself locally to test it. For a role like going out and pitching a client for a contract, the answer is more likely no. To observe how your junior sales hire is doing out in the field, you probably would need to go with them to client meetings for quite some time (unless these are done virtually, and you’re able to join the call in addition to the client).

• Are you able to provide coaching and training on their work output remotely? Even if you can get a good sense of the output, you likely still will need to evaluate whether the organization can provide remote coaching to help the junior hire progress. Can you provide input through shared online documents? Through video calls that walk through problems? By using instant messaging to answer questions? For many types of roles and departments of a company, these tools are well developed, making it relatively easy to provide this support. However, if the role has specific elements that are hard to coach over a video call (for example, the whole-body language of giving a live presentation to a large audience), then you’re unlikely to be able to support that junior hire as well.

• What is your organizational commitment to junior and remote hires? If you’re highly committed to having remote workers, and you’re building a large enough team that you need many junior hires along with senior hires; or if you’re committed to training junior staff on principle, then hiring junior remote workers who have strong professional skills and potential is feasible. If your commitment to remote work is more a case of convenience—you need to fill specialized roles, or you can’t hire enough in any one geographic center—then hiring at the intermediate level and up may make more sense for your remote team.

• Is your organization truly optimized for remote workers? Junior staff members will find their performance more strongly affected by organizational challenges than senior members, who will have developed the ability to get the job done despite challenging environments. If your organizational environment is generally difficult for remote workers, a junior person is unlikely to succeed. Junior staff can navigate role-based challenges, given a supportive mentor, a good manager, and a functional, remote-friendly organization. On the other hand, senior staff can navigate organizational messiness (for example, unskilled management, communication challenges, or a lack of mentorship), given role experience and task-relevant maturity. It is not realistic to expect any hire to navigate both role-based and organization-level challenges at the same time.

​caution​When you add in timezone differences, communicating consistently with a new employee can go from friction to crisis if not handled properly. If time zone overlap between the junior hire and their mentor is low, they will experience long stretches of time where nobody is able either to check in on their progress or to answer their questions. This also constrains task pairing and “showing how it’s done” to a limited time window. Obstacles that might have been overcome with a quick question can derail an entire day. In these cases, a junior team member could take months or even years to become independent at their core job competency. The resulting long learning curve likely has too high a cost to the organization to be worth the training, compared to hiring someone more senior.

There are certain circumstances where hiring is not fair to an inexperienced person with low TRM. These include:

• Your managers are not yet terribly skilled. (For example, if you’re a fast-scaling startup, and many managers were promoted from within and learned through a ‘trial by fire’ experience.)

• Your communication patterns are somewhat ad hoc and chaotic (some things are offline only, lots of different channels, many implicit norms and assumptions).

• Your team isn’t currently able to provide training (everyone is learning as they go and wearing many hats).

A senior remote worker might be a brilliant hire in the exact same situation: no hands-on managers! Lots of opportunities in the chaos! Everyone is trying new things so they can really flex that broad skill set!

​important​This isn’t a case of a “bad” culture. Toxic cultures are harmful to all employees, regardless of experience. This is simply a highly unstructured environment, which is unsuited to low-TRM employees. Remember, higher-TRM folks do better with lower structure. Lower-TRM folks do better with higher structure. Remote workplaces can often be lower-structure workplaces. But it is the degree of structure in your organization that drives your ability to hire junior staff, and not seniority of the staff in question.