remote work guide

What is Remote Work & How to Find It

Want to give your business a competitive advantage? Hire remote workers. Opening up your applicant pool to the entire world with remote work makes it far easier to find, attract, and retain great talent. Many people are thrilled at the chance to work from home or wherever they’d like, so you can get the highest-quality candidates without needing to invest in typical perks like office baristas or complimentary catering. In addition, with remote work, virtual teams save money on physical office space, infrastructure, and other overhead—not to mention fewer sick days, increased productivity, and higher engagement.

As you can see, the willingness to bring virtual team members on board (whether they make up one-fiftieth of your total team or all of it) will definitely help you stay ahead of your co-located competition.

This guide will teach you everything you need to know about remote work. By the end, you’ll understand how to set up your virtual team, hire remote workers, be an awesome remote manager or find your own remote job!

Let’s dive in.

The rise of remote work

It’s worth understanding why remote work has even become possible. It all comes down to one thing: the tools available.

Not that long ago, if you wanted to see whether your employees were being productive, you’d have to physically walk over to their desks and talk to them. Now, thanks to time-tracking apps like Hubstaff, you can monitor their productivity from anywhere in the world (and way more accurately.)

That’s not all. If you wanted to collaborate on a document at the same time as your colleague, you’d need to be sitting next to each other at a computer. These days, you can simultaneously edit the file from thousands of miles away (plus, see exactly which changes each person made, and when).

These examples are just scratching the surface—and later on, we’ll discuss the best tools to use to organize, motivate, and guide your remote force. However, if you have any reservations about remote work, it’s worth knowing there’s probably an app or software program that can solve your specific issue.

How to set up virtual teams

Remote team structures

Before you can do anything else, you have to decide which form you want your organization to take.

On one end of the spectrum, you have completely distributed companies like Buffer, Zapier, Automattic, InVision, and Hubstaff. “Completely distributed” means these companies are operated 100% virtually; you could have one employee in Asia, another in Australia, another in Europe, you get the drift.

In the middle of the spectrum, you have partially distributed companies like Workable and GitHub. A partially distributed team might work across two or three hubs and employ a large proportion of remote workers. Workable, for example, has employees in Boston, Massachusetts and Athens, Greece, along with many who work virtually across the globe.

At the end of the spectrum, you have on-site teams that hire remote freelancers and contractors . Most startups, at some point, fall into this category. They’ll hire a freelancer to do a specialized task; then once they get a little bigger, they’ll bring someone on the team to execute that task full-time. However, some companies build their business model around freelancers. For example, Affordable Staff (a Hubstaff customer) is an outsourcing agency that helps businesses solve their IT issues. The firm’s supervisors work out of a physical office in the Philippines, but the contractors work from home. (Learn how Affordable Staff saved $22,000 a year with Hubstaff.)

Ultimately, the form of your company should depend on your product, business objectives, personal preferences, and more.

You should also take into account the differences between hiring full-time workers and freelancers.


Never before has finding great temporary talent been so easy. With resources like Hubstaff Talent, Upwork, and other popular freelancing sites, you can usually find plenty of people qualified to tackle your work.

Of course, hiring freelancers has other perks as well, including:

  • Flexibility: You can hire someone mere hours after you’ve decided you need help. If you no longer need their services, ending the relationship is simple.

  • Efficiency: Unlike a regular employee, you shouldn’t need to spend a long time onboarding or training a freelancer.

  • Reduced costs: Without insurance, taxes, paid time off, and other benefits, you’ll see your payroll shrink.

What about the cons of hiring freelancers?

  • Lack of control: A traditional employee owes you certain contractual responsibilities, while a freelancer has much more autonomy (for better and sometimes worse).

  • Lack of trust: You’ll usually be working with freelancers whom are new to you, which means it’s really hard to know whether that project estimate or hourly rate they quoted you is fair.

  • Lack of reliability: Just like you can easily let go of freelancers, freelancers can easily let go of you.

While some of these issues come with the territory, using Hubstaff or another time-tracking app can definitely mitigate many of them. Instead of wondering what your freelancers are doing, you can keep up with their work via Hubstaff’s activity dashboard. Rather than going with your gut on rates, you can see just how much each freelancer is accomplishing per hour and make your pay decisions based on that info. Ultimately, you’ll have much more transparency and trust when it comes to your temporary workers.

Full-time employees

On the flip side, you’ve got full-time remote employees. Hiring traditional staff members has many benefits as well, such as:

  • Familiarity: The more you work with someone, the more you understand about their strengths, weaknesses, working processes, and so on.

  • Dependability: Full-timers are usually far more committed than freelancers.

  • Growth potential: By investing in your full-time workers’ skill sets, you can make them even more valuable to your company.

But they’ve got drawbacks too…

  • Higher costs: You’re on the hook for medical and dental, vacation time, software and tech equipment, and other costs.

  • Less specialization: When you hire a full-time employee, you’re probably not looking at how well they can complete a single project—which means looking for people with slightly (or significantly) more generalist capabilities.

  • Inflexibility: The process of hiring and firing a traditional worker is much longer, laborious, and complex than hiring or firing a contractor.

Optimal combination

Questions you should ask yourself to settle the freelancer-versus-in-house debate, include:

  1. “Do I have a sustainable need for a full-time employee?”

  2. “Do I have time to find a good contractor?”

  3. “Is hiring a full-time employee really the answer to my needs?”

Most SMB owners discover a mixture of freelance and full-time talent is the optimal solution.

Structuring your team

Once you’ve begun bringing people on board, you’ll need to figure out how to arrange them. But don’t be surprised if your internal structure shifts as you scale. Take Buffer as an example. In six years, its team management structure has changed four times.

Potential team structures

team structures

Functional Teams

Buffer began with a “one team,” functional approach: one team for product, one team for customer support, one team for marketing, and so forth.

This configuration makes sense when A) you’ve got a relatively small staff or B) you’re not heavily focused on a specific element of your business. To give you an idea, maybe you’ve got four different technical teams, but only a two-person HR team.

Product Teams

If you’ve got several discrete products or services, consider assigning a holistic team to each. This model was actually Buffer’s second. Each team represented one of Buffer’s six products; the team-members were all from different areas of the company, so an engineer might be collaborating alongside a customer support rep and a marketer. Also, there were no bosses: only “decision-makers.”

While the company quickly realized the no-boss policy wasn’t productive, the idea of holistic teams is still very applicable. As Alexander Grosse, Issuu’s VP of engineering, explained, blocking your employees into highly specialized teams leads to delays and information silos. While Grosse was at Soundcloud, he attacked this problem by creating teams that included people from multiple departments.

Task Forces

Next, Buffer moved to task forces. Traditionally, you establish a task force to tackle a temporary or short-term project. For example, you might form a task force to investigate plunging customer satisfaction rates or explore the feasibility of a potential new product.

At Buffer, you could be part of multiple task forces at once.

The benefit of this structure: stuff gets done. When everyone’s working toward a clearly defined goal, the entire organization starts making progress very quickly. Unfortunately, this structure doesn’t work well for responsibilities or functions with no clear end date, like “drive revenue” or “keep customers happy.” There’s also a lot of value in long-term teams: people get used to working together, they establish processes, they become more efficient, and so on.


Hudl, Spotify, and now Buffer use the squad system. Squads consist of five to eight people, each of whom has a distinct and specialized role. Every squad has set goals, but those goals are constantly updated—so it’s like a better version of a task force.

Buffer also uses “chapters.” There’s a chapter for engineers, a chapter for designers, and so forth; these chapters let people with the same roles share what they’ve learned in their respective squads and dive deeper into their specialties.

Incorporating freelancers

incorporating freelancers

As this HBR article by Jon Younger and Rishon Blumberg explains, most organizations do a mediocre job of managing freelancers.

For example, imagine Claret Design Agency just hired a freelance content strategist to develop an editorial strategy for its blog. Since this project falls under marketing, Claret asks its VP of marketing, John Doe, to manage the freelancer. Unfortunately, John has never supervised a freelancer before and has no idea what he’s doing.

Meanwhile, the agency has also hired a freelance developer. This programmer reports to Claret’s technical lead, who’s worked with dozens of freelancers before. The relationship is far more productive than John’s.

See the problem? If you assign contractors to the functional or project manager, your results depend on that manager’s individual strengths.

Fortunately, Younger and Blumberg offer several workarounds.

You can:

  • Assign a roving project manager: this person supports individual managers in planning for, hiring, onboarding, training, and communicating with freelancers.

  • Hire an “external talent officer”: this person is responsible for building and maintaining a strong freelancer network, making sure the existing freelance relationships go well, and promoting the organization as a top choice for freelancer talent. If you hire (or are planning on hiring) lots of freelancers, this option may be ideal.

  • Train your managers: alternatively, you could give your employees in leadership roles lessons in working with contractors.

Finally, when incorporating flexible workers into a full-time structure, look for a tool that’ll provide visibility into their work. For example, with Hubstaff, multiple employees can stay up-to-date on what an individual freelancer is doing—both on a high level and granular level. With this type of information access, managing freelancers doesn’t have to be a single-manager job.

How to post remote jobs

Hiring a remote employee? Fairly easy. Hiring a great remote employee? Much, much harder. To help you find and secure the best remote employees, we’ll walk you through the process from start to finish.

Write a great job description

A job description is essentially an ad: you’re selling a role at your company to a select group of people. But a ton of companies are still writing boring, bland, overly specific ones. That’s great for you, because it means putting energy and time into writing your job post will help you attract the most competitive applicants.

The title

First impressions matter, so don’t blow this one. Your title should include the role’s main function, as well as its seniority level (if applicable).

For example, rather than asking for a “Product Manager,” Plated is searching for a “Senior Product Manager of Operations.”

job title

Anyone who’s browsing a list of open jobs will know instantly if they’re applicable for this one, meaning Plated will get fewer unqualified candidates.

You should also avoid trendy job titles, like “ninja,” “hacker,” “rockstar,” “‘pirate”; basically, if you could just as easily be talking about a character in an action movie, you shouldn’t use that title in your description. As this Recruiter blog post explains, these buzzwords make candidates raise their eyebrows—not apply for your job.

Plus, they’ve become pretty cliche, so you’ll turn off candidates looking for the highest-quality companies.

Key responsibilities

Choose the five to 10 most important things this person will be doing. Zapier recommends filling the job yourself for a week to see exactly what’s required—a tip borrowed from Basecamp co-founder Jason Fried.

Whether or not you do this, make your descriptions as readable as possible. Use friendly, human language (not jargon); use a bulleted list; and start each part with an action verb.


In this role, you will actively contribute to the success of a portfolio of high-value customers; develop a fool-proof success plan to ensure organizational adoptions and expansion of our product; close renewal business on a monthly basis, meeting or exceeding your quota; and develop and close new add-on sales to our existing customer base.


Here’s what you’ll do:

  • Create a plan to help new customers start using our product

  • Make sure our existing customers stay

  • Get new customers

  • Meet your sales quota

See how the second one is infinitely more readable—and appealing?


Here’s where even the best job descriptions usually screw up. You shouldn’t be describing your ideal candidate, because honestly, that ideal candidate probably doesn’t exist—and if you load your requirements with a ton of unrealistic expectations, almost-ideal people will probably skip it.

Basically, as this Workable article explains, you should only include things that you would reject a candidate if he or she didn’t have.

The company & culture

Here’s where you can really sell the job. You want to describe in some detail what your organization is like, your values, and most importantly, how you function as a remote team.

For example, as this Apartment Therapy job description says:

Imagine for a moment...
You wake up in the morning.
Your commute is 45 seconds.
You wear what you like.
You hop on #slack and say what you're going to get done soon (meaning today), your coworkers wave.
You might find yourself answering questions of a junior developer or bouncing ideas off your co-workers about the best way to modularize a piece of functionality you're working on and the benefits of including vs. delegating.

Not only does this list (which goes on) highlight the unique benefits of a remote job, it also shows people what Apartment Therapy’s team is like.

Job search sites for remote work

Once you’ve put together a solid job posting, the next step is distributing it. There’s a long list of sites you can use; however, to get the best results, focus on a legit online job board where the most appropriate people tend to look.

Coding jobs

If you’re hiring programming talent (either full-time or freelance), check out these developer focused sites:

  • Stack Overflow Careers

  • PowerToFly

  • AngelList

  • Toptal

  • Authentic Jobs

Graphic design jobs

If need creative skills for web or print, check out these designer job sites:

  • Dribbble

  • Behance

  • Working Nomads

General remote jobs

Telecommuting only job sites to post opportunities ranging from executive, marketing, IT or data entry work:

Find the best candidates


Hopefully, once you post your job description, the applications will start rolling in. Here’s what to look for during the interview process.

Highly self-motivated

Your workers will be controlling their own schedules, which means they need to be independent and ambitious.

To screen for this trait, ask candidates what management style they prefer. If they say they like autonomy or minimal supervision, that’s a good sign. You can also ask them to describe their working style; look for answers like, “I look to my supervisor for high-level goals, but I prefer to figure out how to achieve them,” or “I like checking in with my boss every once in a while, but in general I’m fairly independent.”

Good at writing

Most remote team communication takes place over writing, whether that’s in a Hubstaff Tasks project, Asana thread, or Trello card. That’s why, as Sujan Patel explains, it’s crucial your remote workers can write well: miscommunications will quickly slow down your projects and even lead to personality conflicts.

First, when you’re reviewing a candidate’s application, look for evidence they can write. Even if you’re hiring an engineer, maybe they wrote a post for their company’s blog or discuss tech on their Medium account.

During the interview, ask candidates how comfortable they are with writing. You can also ask, “How do you make your written messages clear and understandable?”


Because your remote workers will be collaborating across thousands of miles, it’s even more important to hire people who work well with others.

Look for candidates who have experience in team settings. Furthermore, you should ask each person you interview to share a time they successfully worked with a team, along with a time things didn’t go so well. Follow up by asking which factors made the difference, and how they’re applying those insights.


Many remote work experts will tell you to look for highly trustworthy candidates; after all, you’ll be relying on these workers to do their job even without any oversight.

But “trustworthy” is hard to define and even harder to spot. It’s not like candidates will advertise their dishonesty or disreputability.

Luckily, Hubstaff and other time-tracking apps mean you can prioritize the other traits we’ve discussed. These tools keep track of your employees’ work-time activities and productivity levels, so you don’t have to worry that, say, your freelance developer is charging you $1,000 for a $100 job, or that your full-time community manager spends all his time playing online poker.

That’s not to say you should hire anyone who sets off internal alarm bells. But you can relax a bit knowing Hubstaff will save you from slackers or demotivated workers.

To make sure you don’t hire anyone who will feel uncomfortable with remote work software, say, “We rely on Hubstaff to keep track of individual and team progress, keep productivity high, and make sure you’re paid for every single second you work! If we brought you on-board, would you have any issue using this tool?”

Managing virtual teams

You’ve invested a lot of care and time into the hiring process, and as a result, you’ve got a great group of people ready to turn your vision for your organization into a reality. Yet managing a remote team is different than running a co-located one. Here’s how to onboard new members, virtual team building activities to create a strong culture, and resolve issues.


Don’t underestimate the power onboarding has to make—or break—an employee’s experience. Imagine you’ve never worked remotely before, and you’re a little apprehensive about the transition. On your first day, you receive clear, detailed instructions, get a warm welcome from the team, learn exactly what you’ll be doing in the coming months, and discover which tools the team uses. You’d probably feel far more confident and empowered to do well, right?


First things first, send your new hires the forms you need them to sign and complete. If you’re working with freelancers, you’ll need a contract outlining the project or assignments; deadline(s); rates and payment details; and an ownership clause, if necessary. Full-timers, on the other hand, will require your standard forms for employment, insurance, compliance, and so forth.

DocuSign and HelloSign are both fantastic options for sending files back and forth. And if you want to make the process more seamless still, check out Zenefits’ onboarding software.


Your new hires should clearly understand two sets of expectations:

  1. Your universal expectations for communication, behavior, quality of work, etc.

  2. Your role-specific expectations, i.e. what you’d like to see them accomplish in their first 30, 60, and 90 days on the job

So, at some point during their first day, set aside an hour or so to have a video-call and discuss both.

Ideally, your team-wide expectations would be recorded in a company manual. (Check out this When I Work article for tips on writing an employee handbook!)

Your individual expectations for each employee should be recorded as well; try putting them in a shared Google Doc or other mutually-accessible file.


At HubSpot, there’s only one policy: use good judgment. However, not every company takes such a broad approach; you may find it necessary to establish multiple policies, from social media best practices to your stance on side gigs.

Those guidelines will be covered in-detail in your team handbook, but it’s worth covering the most important ones face-to-face (that is, webcam-to-webcam).

For example, if you use Hubstaff, you’d probably want to discuss that again. You might say:

As we talked about during the interview process, the team is a huge fan of Hubstaff’s time-tracking software. Rather than having to submit daily reports or create invoices, all you have to do is download Hubstaff to your computer and start the timer when you begin working. It runs invisibly, so you’ll only remember the app when you’ve finished work and want to stop the timer. Your manager will see what you’ve been working on and how much time you spent—and great news, we’ll pay you through Hubstaff. You’ll never get a too-low or late payment again. Finally, one of the Hubstaff features we use is screenshotting. While you’re working, the app will take a screen-grab at random moments. If you don’t want the screenshot saved, you can choose to delete it. The app will simply deduct the corresponding chunk of time from your records.

This explanation is effective because:

  • It clearly outlines the company policy

  • It provides the rationale behind the policy

  • It describes how the policy benefits the employee

Virtual team building activities

With a little creativity and thought, you can create a remote culture that’s just as healthy and impactful as a traditional one.

Traditions that foster unity

Even though your team will be working from all over the map, you want them to feel like their company friendships are just as strong—if not stronger—than if they were all in the same town. Traditions are a great way to accomplish that: not only can you build employee bonding into your regular work life, but you can also promote a sense of fun and free-spiritedness.

The Help Scout team stays connected by hosting "Friday Fika". Each week, the Help Scout team members talk with another randomly chosen coworker for 15 to 30 minutes on any topic they’d like. To make things feel even more fun, each person shows up to their “coffee date” with pastries and a caffeinated beverage.

You can borrow tons of ideas from Buffer. The company uses a shared hackpad to publicly track each individual’s goals, so everyone can support their team members’ growth. In addition, Buffer has “theme” days on Sqwiggle, a chat and video app; one day, everyone took a picture wearing sunglasses, while another day, they all posed with thumbs-ups. The team’s “mastermind” tradition is also pretty cool and unique. Every seven days, each employee gets together with the same partner to talk about high-level challenges and accomplishments. Since their fellow mastermind never changes, they can really create a sense of trust.

You may want to take a page out of Trello’s book as well. Twice a year, the company holds Remote Week: a chance for the 50% of its team that works remotely to meet the 50% that works out of the NYC offices. In addition to plenty of food and fun activities, Remote Week involves meetings, planning sessions, special breakfasts, and design sprints.

Issue resolution

No matter how much time and thought you spend designing the optimal remote work environment, conflicts are inevitable. If you want your team to weather these conflicts like champs, set up the right methods for dealing with them.


As Keith Ferrazzi, author of Never Eat Alone, explains in this HBR article, people tend to have way less restraint in virtual environments than real-life ones—meaning it’s easy for a task-related conflict to turn personal.

Ferrazzi suggests having conversations out in the open is the solution, for several reasons:

  1. When everyone has access to the same information, you can resolve conflict before it turns toxic.

  2. Your team members can tackle an issue as, well, a team. Each employee can study the question on their own time and then propose ideas.

  3. The more transparent you are, the more trust you’ll create.

Being transparent can also help you preemptively avoid conflict. For example, when Yesware hit 96% of its revenue goal, the team could’ve been worried about the reaction from the board of directors. However, since the company’s CEO always shares the deck and board feedback from his meetings, his employees trusted him when he came back and said, “We came very close to an ambitious goal—they’re pumped.”

Video calls

It’s really easy to interpret other people as angrier or more upset than they really are when your only context is their words. If two or more members of your team are clashing, insist they hash things out over a video call.

You (or another higher-level employee who can act as a mediator) should guide this call. Here’s the basic process for conflict resolution:

  1. Explain that you’re a neutral third party, and the goal of this call is resolve any disagreements or differences that’ve cropped up.

  2. Lay out the ground rules: each person must be respectful and give the other time to talk.

  3. Ask one employee to share his or her perspective; then, without commenting, ask the second employee to voice his or her own perspective.

  4. Lead both employees in creating a shared agenda. For example, if one person is annoyed that her co-worker never responds to emails in time, one goal might be for the co-worker to message back within 2 days. A second goal might be for the first employee to send timely requests earlier, so she gives more warning.

  5. Have both employees verbally commit to these goals.

  6. Schedule a date for a check-in meeting, at which you’ll discuss their progress.

Using the Right Tools

remote management tools

Running a remote team might be difficult, but it gets way easier when you introduce the proper tools into the mix.

Tools that enable teamwork

In the section on hiring remote workers, we talked about how important it was to hire people who can write well (or at least clearly). Luckily, you can go way beyond the written word with communication and collaboration tools.

First, you’ll need a chat platform. Slack is one of the most popular chat tool used by companies that are embracing the remote work methodology.

You’ll also want a project management tool, which’ll help you organize ongoing work, delegate responsibilities, keep track of deadlines, and most importantly, keep the team in sync. We’re big fans of Asana, Wrike, Trello, and Liquidplanner, but honestly? You’ve got a wide range of options. Check out our guide to 30 online project management solutions.

Next, figure out which app you’ll use to share and collaborate on files. Some teams, for example, love using Google Apps for Work, which lets you easily send around and co-edit spreadsheets, text documents, photos, and videos.

Tools that enable productivity

To guarantee your employees are putting in their best efforts, download Hubstaff or a different time-tracking app. With Hubstaff’s lightweight solution, your workers will always have a reason to stay on-track. Plus, they’ll gain increased understanding of their work habits—to give you an idea, maybe your graphic designer realizes she always has trouble focusing around 3 P.M. With that knowledge, she can decide to take a one-hour break in the afternoon and then return to creating graphics completely refreshed.

Hubstaff also streamlines the invoicing and payment process. It integrates with PayPal, Payoneer, Bitwage, and QuickBooks, so as soon as your freelancers or full-time employees log their time, you can pay them in less than five clicks.

However, that’s not the only app that’ll boost your (or your team’s) efficiency. We’re big fans of Alfred, a Mac app that lets you use hotkeys and keywords to do everything more quickly. You can even set up customized workflows using Alfred’s powerpack.

LaunchBar is another solid option (thanks Todoist contributor Zachary Sexton for the tip!). First create your own keyboard commands, then use them to launch apps, files, bookmarks, and more. Whenever you need to find something (literally anything), bring up the search bar to quickly perform a desktop or web search.

By never lifting your fingers from the keyboard, you’ll save tons of time. Gift Alfred or LaunchBar to your employees to make them speedier as well.

Focus@Will is worth the investment as well. It’s like Spotify or Pandora, but specifically for music that’s scientifically proven to boost your concentration. It also comes with a productivity tracker, so you and your employees can see which music was most effective at getting you in the zone.

Finally, everyone on your team should have some sort of time zone app. The SuperheroYou folks like WorldTimeBuddy, which gives you a handy dashboard of locations around the world with their respective times. When you’re trying to coordinate meetings between people several hours off from you (and each other), being able to instantly calculate their local time is invaluable.

Congrats—you’ve reached the end of our guide to remote work! At this point, you’re equipped with all the knowledge you need to manage your distributed team.

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