Youβre reading an excerpt of The Holloway Guide to Remote Work, a book by Katie Wilde, Juan Pablo BuriticΓ‘, 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.
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 rolesβfor 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 wonβt 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.
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 weβve 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 thereβs an office they can/will need to go to occasionally, and any other details (for example, βU.S. remote onlyβ or βtime zone agnosticβ).
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
βimportantβIn the title of the job post title, itβs best practice to list βRemoteβ(geographic region)β in the location field of the job posting. For example, where a non-remote job posting might advertise βQA Analyst, Atlanta GA,β the remote version would be βQA Analyst, Remote within the USA,β βQA Analyst, Remote within Eastern Standard Time,β or βQA Analyst, Remote (global).β 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 wonβt reply to a remote position, and of course, candidates who arenβt in that location wonβt 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 youβthe employerβto customize perks and benefits (for example, instead of βcatered lunch,β perhaps you offer a lunch stipend).
βTo remain productive, effective remote workers need to be able to give themselves structure without the crutch of a standard office environment.ββGreg 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). Youβre 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, itβs table stakes for someone on a remote team. They wonβt 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 someoneβs ability to work remotely, they donβt 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 didnβt 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. (Thereβs nothing wrong with a traditional in-office background; it just doesnβt provide any insight on this specific point.)
If a candidate has worked remotely, itβs much easier to ask them about their specific experience and determine whether theyβll succeed. If they have not, you can ask them about what challenges they expect, and what adjustments they plan to make. Youβre looking for thoughtful, specific answers. Successful remote workers tend to be self-structuring people who prefer to make plans and stick to them.
βcautionβIf candidates are blasΓ© 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 theyβre getting into. Youβll 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 theyβre happiest during the workday, and about times theyβve felt especially fulfilled or frustrated at work. Itβs 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 theyβre 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?
βimportantβOf 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. Itβs 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 youβre discussing your team, itβs 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 youβll want people to know what working at your company is really like, so that if they know they wonβt 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 youβre truly seeking to understand whether they will enjoy the environment. This includes clarifying that itβs not a test and thereβs no hidden agenda; you both want to find a situation that works for everyone.
If a candidate will be remote, itβs important to assess how they come across in the context of your remote team. Youβll 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 youβre hiring for calls for mainly written communication, some video discussion, and a lot of audio-only calls (for example, conference calls), then itβs 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 wouldnβt 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.
βimportantβIf your company has co-located employees as well, itβs important to use the same methods to interview candidates who wonβt be remote. Theyβll have to be working using the same mediums as remote employees, and will be communicating more asynchronously and in writing as well, so you wouldnβt want to presume theyβll 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 languageβnonverbal communication competenceβdirectly 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 personβs ability to transmit or interpret information via nonverbal communication, such as clothing, body position, gestures, and facial expressions.*
βcautionβThe 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 canβt use the body-language skills that they rely on to communicate, and their written and verbal communicationβwhich didnβt get assessedβturns out to be inadequate.
To avoid this trap, youβd 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.
Itβs 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. Itβs 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. Microsoftβs 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 βheβ? 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 theyβre 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.
βcontroversyβA common attitude when hiring remote roles is that itβs 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 isnβt the full picture.
When companies say things like βitβs basically impossible to have a junior remote worker,β what they often mean is βa remote worker who lacks strong communication skills and professional skills like goal setting and independent action will fail.β And to some extent, thatβs 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 doesnβt 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, letβs restrict the discussion to junior staff who also have strong professional and communication skills, presuming this is what youβll screen for. In this context, it helps to clarify what βjuniorβ means. A helpful concept is task-relevant maturity.
Task-relevant maturity (or TRM) is an employeeβs 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 itβ[their] task-relevant maturityβ¦ As [their] work improves over time, you should respond with a corresponding reduction in the intensity of the monitoring.*
Someone who is βjuniorβ 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 βseniorβ in this sense has relatively few areas of low TRM, and thus rarely needs monitoring or training.
βimportantβWhen people say itβs impossible to hire junior people to remote roles, the underlying truth may be that the company hasnβt 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 canβt do that, there are likely to be other problems down the road for their remote staff, no matter their experience.
Monitoring and training a junior employee will be harder in a remote context. When you canβt look over at what theyβre 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 questionsβor 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 canβt just say, βHowβs it going today?β as they walk past the new employee to get a cup of coffee, and they canβt 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 doesnβt have these kinds of communication paths and documentation set up, it wonβt just be the new junior person who suffers.
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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 donβt have to be. Itβs completely possible to be a structured, remote workplace.
If youβre remote, youβre 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 youβre remote per se, but rather is because you didnβt provide the structure that a low-TRM person needs to learn and succeed.
If youβre 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.
βimportantβThe point here is that the level of structure a workplace provides should best be tailored to the remote workerβs 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. Itβs also worth noting that an exhaustive handbook with timezone-agnostic detail for onboarding new people is critical when spanning large temporal gaps.
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. Itβs 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 youβre 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 youβre unlikely to be able to support that junior hire as well.
What is your organizational commitment to junior and remote hires? If youβre highly committed to having remote workers, and youβre building a large enough team that you need many junior hires along with senior hires; or if youβre 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 convenienceβyou need to fill specialized roles, or you canβt hire enough in any one geographic centerβthen 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.
βcautionβWhen 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 βshowing how itβs doneβ 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 youβre a fast-scaling startup, and many managers were promoted from within and learned through a βtrial by fireβ 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 isnβt 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!
βimportantβThis isnβt a case of a βbadβ 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.
βcontroversyβCompensation for remote employees is a controversial topic. What happens if someone changes locations as a remote worker, moving from an expensive city to a much cheaper location for a better cost of living? If another worker were already in that location, would you end up with two people doing the same relative job, but getting paid vastly different amounts? Thereβs no surer way of undermining the trust between distributed team members than having an inconsistent, unfair compensation structure.
Ultimately, there are two broadly consistent approaches to modeling compensation that you can use for distributed teams:
A global salary model for compensation of remote employees pays everyone the same fixed amount for the role and experience level.