How to Hire Remotely

Hiring Remotely

I previously wrote on How to Work Remotely. Now, I throw some tips out there from the other side. While I’ve worked remotely for over a decade, I’ve also hired and managed teams remotely on several occasions in that time as well.

I would have to say that the most important lesson that I’ve learned by having experience on both sides of the hiring process is that it’s very much a two-way street. In other words, a hiring manager, as much as they like to think they do, don’t actually hold all the cards. It’s just as important that a potential employee actually find their work and work environment to be a good fit. I’ve lost count of the rude and arrogant hiring managers that I’ve had to deal with. Don’t be one of them.

The way most people think about the interview process is probably a little dated. It shouldn’t be one-sided; it should be more of a conversation than an interview. With that said, both sides certainly need to have a filtering process to narrow it down to hopefully find a mutually good fit.

Step 1: Get Over Your Insecurities

Most white collar jobs these days can be done remotely, including jobs in industries like: web design, graphic design, marketing, writing, photography, consulting, teaching, trading, betting, music, video game development, real estate, running an online store, product, or service, etc. Of course, this no doubt doesn’t really apply to blue collar jobs, service industry jobs, engineering, etc., which will always require someone in-person.

However, I still see it daily, people that can hire remotely, but limit themselves by screaming “LOCAL ONLY!”, “Must come to my home!”, and other stupid, counterproductive and counterintuitive shit from the rooftops. I generally keep my language pretty clean on this blog. However, this is a huge pet peeve of mine and requires some serious emphasis. I see so many dinosaur companies with dated methodologies and control issues, unnecessarily paying overhead for office space, materials, electricity, internet, company computers, etc., because they’re just too afraid of change or that their workers will slack off if allowed to work from home.

Drum roll please… if you’re limiting the talent you can reach to just your hometown or cutting into your profit with ridiculously unnecessary overhead, you’re fucking stupid! Knock it off. Knock it off right now. It’s time for you to come into the 21st century, dragged kicking and screaming if necessary.

Step 2: Where to Look

This isn’t as easy an answer as it used to be. Try to avoid middlemen as much as possible. That is, these services that force you to communicate with professionals via their website and also take a cut of payments you send to professionals. This is just a really shitty way to work both for you, the employer and the employee.

Honestly, I recommend avoiding some of the most popular job boards like: Monster, CareerBuilder, Indeed, etc. I also recommend avoiding more niche boards like: Freelancer, Upwork, Guru, etc.

craigslist, on the other hand, even with all the spam, scams, and garbage you have to navigate through, still remains a very worthwhile place to find people. craigslist is a double-edged sword in that the reason it’s so popular among legitimate people, is the same reason it’s popular among shady people: it’s free. If you can condition yourself to see through the BS like I have and see just the legitimate headlines, it’s a resource that will always be useful.

If you can’t or don’t want to, however, there are some hybrid sites that have been popping up where they charge hiring managers a fee to list jobs, which effectively cuts out all the spam, while still allowing clients and professionals to connect with each other directly without any middleman interference. The only remaining problem, they charge too much! We’re talking $100, $200, and more.

So, as they say, if you want something done right, you’ve got to do it yourself. With my over ten years of experience both hiring and being hired remotely, I feel that I’m in the unique position to build the best remote job site there’s ever been, pulling all the best parts of what makes connecting people work together and keeping it affordable. I created:


A beautifully simple and to the point job listing site that only asks $30 for a listing and then gets the hell out of your way.

Step 3: The Filtering Process

Now that you have a hundred or more applicant emails in your inbox, the real work begins. The extent to which you would like to make applicants jump through hoops is up to you, but remember not to be an asshole about it. The process shouldn’t just help you find candidates that are a good fit for you, but for them to learn if you’re a good fit as well.

Step 3a: Introduction

Personally, I like to keep the first test simple. Just allow them to email you and go from there, deleting emails with immediate issues or red flags at just a glance, things like:

  • Issues with literacy or fluency in the primary language the position calls for
  • Really sloppy emails with poor presentation and grammar
  • Canned responses (depends — see below)

At least for me, canned responses aren’t necessarily a deal-breaker, if it’s craigslist. The way craigslist is set up, the sheer number of listings generally calls for canned responses. There just isn’t enough time in the day to personalize every email. For RemotelyHireMe, however, and similar sites, a email that isn’t personalized should be seen in poor taste.

Step 3b: Research

Now that you’ve deleted all the garbage emails and have your keeper emails, it’s time to take a closer look:

  • Google the person’s name
  • Go over their resume and portfolio
  • Review their social media profiles, especially LinkedIn
  • If they’re a digital professional, but don’t have their own website, I generally consider that a red flag

Step 3c: Discussion

Now that you’ve narrowed it down to your most wanted candidates, it’s time to actually discuss with them. What’s their schedule like, what the work entails, the pay, etc. There’s a saying, something like:

As it begins, so shall it end.

In other words, if you’re having a difficult time communicating, finding a good rapport, maybe it’s best just to go with your gut feeling and pass. You have no obligation to “try someone” just because.

Step 3d: Trial

This is perhaps the most important piece in the whole process, and yet the most ignored. There are no guarantees in life. No matter how much you vet someone or how much they vet you, there’s no way to know for sure if it’ll still be a good fit once the work has actually begun. In fact, when I’m being hired, I strongly recommend that we do a week trial.

Some people get it and understand it’s a good idea. Others are a bit more stuck on “how they do things”, wanting you to just commit. Anyone who commits to something they haven’t even tried yet are simply lying to make the boss happy and get the job. But, you know what, if after a week, they’re miserable and are thinking they made a big mistake, there’s really nothing to stop them from walking right out the door.

It’s always better to just be honest about such realities and put the pretend niceties aside.

It’s Never Been About the Lack of Work or Workers

Whether you can’t land a job or you can’t find workers, it’s never been because they weren’t there. That was never the struggle. The struggle is finding and building relationships. And like any relationship, a working relationship is difficult. You’ve got to find each other and it’s got to be a good fit. In other words, as hard as it is for people to find good work, it’s just as hard for others to find good workers. Once you find it, hold on tight.

Pay and treat your workers well and they’ll give you good work.