Running and growing a business can consist of a barrage of growing pains, awkward conversations, and a desperate searching for the right partners, hoping that things will work out. In the entrepreneur’s world, your partners are your employees. Virtual employees can be quick, efficient, produce top-quality work and help your company gain new ideas and fresh talent. By utilizing strategy in your approach, you can find excellent new members for your team.

Comic strip from autodesk360

Comic strip from autodesk360

Our remote hiring and management experience at Hubstaff runs deep, with decades of winners and “not quite winners” to boot. Hiring remotely is its own special animal.  Here’s our process for finding and hiring awesome virtual employees.

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1. We look for skill first and foremost

Skills are the number one, top identifier in qualifying your remote hiring prospects. However, if you don’t know what you’re looking for (i.e. can you tell if a coder’s php is up to snuff?) then you may not be asking the right questions. Read more about evaluating technical skills here.

Spend some time assessing how you can qualify candidates in a field you don’t fully understand, and if you hit too many road blocks think about contracting a specialized recruiter to vet them for you to start. Have them coach you in what to look for.


In the spirit of outsourcing – let the prospect make the first move. Look at how they identify themselves in professional arenas. If they label themselves as a graphic designer, then why are they applying for your bookkeeping job?

As a general rule at Hubstaff, we recommend that virtual employees be specialists, hired contractually for very specific purposes. Chances are they’ll be great at it and you’ll get more for your money, faster.


How does his or her presentation vary across professional networks? Is the messaging the same, or at least intentionally segmented? Is their profile complete? Think about this logic – if they half-ass for themselves it’s very likely they’ll half-ass for you.


Does the prospect give any indication that they actually care about their trade? Have they blogged about it, spun it off into a side project or joined any trade groups?

Their work history doesn’t have to be cohesive, but it should convey a trajectory that positions them where they are now – facing towards where they want to go.

Next Step: If a prospect has perked your interest either in his or her portfolio, work experience or overall conveyance of skill sets then it’s time to get them on the horn.

A Note About Communication

Keep a hierarchy of mediums ranging from highest fidelity to lowest. If a remote hire happens to be in your city, then it behooves you to meet them in person. You don’t have to go overboard in your interview or time commitment, but face to face will teach you more about their presentation, personality and future growth prospect (hopefully in your company) than months of remote ping pong. Here’s a list of preferred medium from best to worst:

  • In-person meeting
  • Video Chat
  • Phone Call
  • Chat
  • eMail
  • Smoke signals (still with us?)

2. Pay Attention to Personality Traits

It might not be as important for your cave-dungeon coder to be as chipper as your Sales Associate but it also doesn’t mean you go out of your way to hire the developer equivalent of a cat lady just because they can rock out on a DVORAK keyboard while listening to Meatloaf.

When you engage a prospect, several factors will race through your head – all of which are important. As a final tie breaker, never be afraid to go with your gut.


It’s not ethical on your part to try and entrap a candidate, but does their story make sense? Are they accurately conveying a firm grasp of their subject matter? How about this one: are they actually as excited about the work as they say they are?

Don’t break any HR laws (do they exist in the remote world and when you hire online?) but a candid professional question on your part can often be the defining moment that not only breaks the ice, but brings out the truth in a candidate. i.e. “do you like resizing ads all day?”


You’re an entrepreneur. I’m probably not the first person to reveal to you that it’s highly unlikely anyone will ever care about your company as much as you do. But, that doesn’t mean you should accept a staff of workers who are bleeding you dry while putting in the minimum amount of effort possible to get by. You need to hire a freelancer who will put effort into his or her work and devote all the time needed to get a job done well.

Some freelancers rarely take days off

Some freelancers rarely take days off

How can you tell if an employee cares about your company? One easy solution is to hire your customers, specifically someone who is an existing user or someone who “fits the bill” of your target audience. The value of doing this is that as the hire grows in your company they’re much better positioned to add value to your customers (if outward facing) and can be a stronger part of your brand story.


In my past life before Hubstaff, when I was young lad coming up the ranks, sometimes I would leave an interview feeling great and then never heard back. I never knew why. Now that I’m on the other side of the “desk” I realize that questions are hugely important for validating how much interest a prospect has in working for you.

But the questions your candidates ask should be about your company and the work – NOT, the hourly rate, the work hours, the benefits and everything else that’s directly benefiting them. Candidates that can’t get past “what’s in it for them” aren’t interested in partnering with you, they’re looking for a transaction.


Forgive the fancy term, it was too good to pass up. Depending on the role that you need to fulfill and what stage your company is in, having multi-faceted team members is a solid way to grow your company. These virtual employees can easily adapt to your growing needs, and may be able to stick with you as you move to the next level.

Death by Questionnaire

As mentioned above, questions are a great qualifier in bringing on a new hire. But, everything should come in moderation. It can get to a point where your potential hire is asking so many questions that you beginning to question his or her competency and ability to fulfill the role.

Keep in mind that in a virtual setup, more questions may be necessary to understand different processes. It is more challenging to communicate online than in person in many ways. However, there is a limit to how many questions are useful in an interview or in a working process.

The Stickler

If someone can’t get past the fine print of your offer before you even start talking about getting work done, they’ll only get worse. Good remote employees are notoriously good at finishing the work now, and figuring out the details later. That doesn’t give you a license to scrap your workflows with reckless abandon, but it does mean if someone shows up to the interview with a magnifying glass then it’s time to dip out the back door (kidding…kind of).

Sweet 16

This is a prospect, and maybe even new hire that right off the bat you can tell is so uptight they’re going to treat every task and project like their Sweet 16 party with pony rides, gift bags and ultimate “bridezilla-esque” nightmares for everyone involved. They time-suck every task with monotonous details that don’t benefit the end customer or the team. You gotta crush those dreams, sooner than later. Easy going, pleasant and flexible is the name of the game. Remember: #sempergumbey

3. Remember… You Can’t Change People

We say this a lot. This is not to be confused with “people don’t change.” Do yourself a favor and be brutally pessimistic about any hope that an “okay” prospect will ever convert into a top-performer by any action of yours.

Drive. Drive is what will elevate a remote worker more than any outside force. Mentoring is great, plus communication and relationship building are all essential to growing a distributed company, but you have to recognize drive.

What does it look like? It’s easier to identify than you think, just don’t confuse it with its evil cousin, folly.

One candidate shows up on your digital doorstep and has a cornucopia of well-intentioned but half-baked projects. They’ve got ambition, but they’re not closers – and are lost in folly.

The other candidate with drive may show up seeming like she or he has a ton on their plate but they are crushing it on all fronts and you can smell the synergy dripping from their samurai sword. (Man, that was a ton of corporate lingo mixed with Kill Bill…)

Recognize that good hires who show drive still need your guidance and advice. If you’re doing your part, you’re bringing them along for the growth and they’re adding skills along the way.

If you’re seeing red flags, even tiny ones, it will never be worth the headache or risk. This would be your opportunity to present candid feedback. Ideally they’ll appreciate it, and who knows – maybe they’ll prove you wrong down the road.

4. Show Me Whatcha Got

No, this doesn’t mean each candidate provides you with a video of their winning urban dance-off, but it does mean you should think about easy exhibitions for your prospects to demonstrate their abilities.

Dealbreaker Skills

In the online world, writing is everything. They don’t have to be Proust on pixels, but if you’re in a communication-heavy industry, the inability to write on a somewhat enticing level needs to be a dealbreaker.

What are the skills that every hire in your company needs to represent? Maybe you’re in a specialty business and each hire should be an aficionado. You have to figure that out.

Test Tasks

It never hurts to give a prospect a small project (pay them of course) to see not only the quality of their work but what their process is in achieving the goal.

Tests might be literal, ie. solving a block of code or designing an ad. But what could you have them do that not only brings out their skills, but their personality as well?

A conceptual test might be “send us a mobile phone video tutorial on how to tie a shoe – bonus points if you can add effects to it.” Small hurdles, like adding the effects, are immediate qualifiers in who makes it to the next round.

Ammunition vs. Barrels

This concept came up in an edition of Y Combinator’s “How to Start a Startup” and it’s a great funnel for testing, categorizing and keeping your top performers.

Basically Keith Rabois explains that adding people at a rapid rate, which often happens in startups, is adding ammunition. But, ammunition is essentially unrealized firepower until it is coupled with a barrel (and a few other parts but let’s keep it simple) to ignite it and bring it out into the open (ie. the market).

“The definition of a barrel is they can take an idea from conception and take it all the way to shipping and bring people with them.” [Tweet]

Every “round” of ammunition should be given small tests as opportunities to find out if they’re actually barrels. Barrels tend to be very specific to a culture, and therefore you should do whatever it takes to retain them – better relationship, more pay, equity, a space in front of the Tesla charger, they name it.

5. Go Where the Fish Are

We’ve been diving deep into what to do with the hires when we find them, but…where does one find them in the first place?

The acquisition process can be broken down into two categories: active arenas and passive arenas. It’s essentially hunting and fishing.

Passive (Fishing)

These are the sites that allow you to post an opportunity, and you wait for the talent to come to you. We’re big fans of Angel List for finding top talent that’s tech savvy and adept at working in the remote environment. They also have a really streamlined application process that makes it easy for people to connect.

Our approach to this is generally posting a job with a base salary and then through our interviewing and vetting process we test applicants and negotiate an hourly rate. Read more about why we prefer hourly work vs. salaried in one of our guides on remote team management.

Angel List is not the only place where you can find great freelancers. Here are another 10 sites where you can find your next star employee.

Active (Hunting)

Social Networks

One of the key benefits of a LinkedIn Premium account is the feature that allows you to search for persons outside of your network and message them directly with opportunities.

Another benefit is that you can target your search towards professionals in countries with a favorable arbitrage with the dollar (e.g. The Philippines, Jordan or India). This is useful if you have budget considerations since you can capitalize on low cost of living in different areas.

Popular Sites

Does your industry center around several key sites that tend to drive the trends and content? For Hubstaff, we like to look at who’s making waves on sites such as Stack Overflow, Growth Hackers or Quora. Who’s answering questions and being preemptively helpful? Hey – that sounds like a good employee, right?

Always start small – ask if they’re up for doing some freelance work, get them on the “phone” and see if they’re a good fit.

6. The Law of Attraction

The best virtual employees don’t seek out boring, disdainful working environments. And if top performers do happen to land in that kind of environment, they don’t stick around for long.

Want the best virtual employees? Create a good environment and attract them with respectful communication, a good title and an acceptable rate of compensation. Also understand that compensation is only one component of what makes a job desirable. The quality of the work, opportunity and working arrangements are all important variables.

It’s A Numbers Game

Remote recruiting often comes down to getting a handful of candidates and hiring the best two or three. When sourcing, we often find that our passive pursuits might yield one good candidate out of 10 applicants, whereas active search might require contacting 10 professionals before one reply. It’s important to mix your approach so that you can hone it, and also to get a more diverse pool of talent.

When you have a firm grasp on what’s working for your business, it’s time to systemize it.

7. Outsource the Outsourcing

As an advanced digital recruiter, you should have records of your optimal pitch post and your best testing tasks to vet applicants.

How can you take your time investment out of the equation? Could a virtual assistant (VA) post the jobs for you, then send job applicants an automated email with a task to perform?

By the time an applicant reaches you, they could go through two to three stages of automated vetting. Scheduling time to meet with prospects is hugely time consuming, so why not create a final step where they schedule a block of your time though a calendar program?

Look for the opportunities to step out of the away and let your experience do the work for you in the way of smart systems.

Learn how Hubstaff Talent can help you find awesome virtual employees.

8. The Bonus Section

We wanted to include this section of “miscellaneous realities” that we’ve found helpful in bringing in top remote talent.

Don’t be afraid to offer a better job

If you have an applicant whom you recognize as being undervalued in his or her current position and you want him or her on your team, then you have a perfect opportunity to offer a step up, a better title, more flexible workflow or better pay. Think about what the person on the other end of the line is really looking for.

Good workers always have a job

It’s definitely best to trust this as a constant. Many of your best remote workers will have full time jobs or ventures of their own, but are looking to branch out or hone some additional skills. Propose a starter project with them to see how it goes, and if it plays out well, then that becomes your opportunity to hire more of their time and efforts.

Reiterate: Don’t Hire Pains

People don’t change, and people who are hard to work with at the onset will likely only get worse. Trust us on this one.

Happily Ever After?

If you’re up for the challenge, the rewards of remote management are obvious and the opportunity is growing. You and your virtual employees can enjoy the ultimate freedom of time and place, with work expense directly tied to productivity. Continuing to develop yourself as a remote manager will make the cycle of hiring, growing and progressing even easier.

Stay focused on skills, personality and the basics of management and you’ll be well on your way. For more advice on how to hire online and maintain remote teams, check out: