For many companies in our now-more-than-ever digitally enabled society, for cost-savings or a myriad of other reasons, many are beginning to embrace the idea of utilizing remote workers. The prospect of using a freelancer has become pretty common, but it used to consist of hiring your friend or brother-in-law. Minimally, someone within a stone’s throw. But with advances in tech, the world has gotten smaller and good help further away all at the same time.

Recently, I hired a freelance remote worker to assist on a project my team was working on for a client that required specific expertise. Unfortunately, our engagement didn’t go that well. However, the good news here was that there were a handful of learning opportunities throughout worthy of sharing to help others make educated decisions when hiring resources online.

The reasons for going with a remote resource are many and honestly deserving of an article on the subject alone. But for this piece, I’ll explain the choice we made. Our company is what we have lovingly called for north of a decade a “virtual agency.” Mostly we are a small team of in-house resources (account management and senior art direction) and masters of a broad network of skilled contractors from every discipline you can imagine. For each client project, we develop bespoke teams of professionals suited to achieve their goals and ensure excellent results.

Occasionally a project comes along that needs a skillset that our current network isn’t chock full of, usually experts in new or burgeoning technologies. This was the case with our recent hire. We use several resources on-and-offline when we start our search. Most commonly, its word of mouth or referrals which we have found net out the best talent and the best relationships. However, when our network runs dry, we use other tools of the trade to track down talent. In this case, we used a platform called Upwork (formerly Elance) to find prospective help.

Within 15 minutes of posting our position, we had more than a dozen applicants from which to choose. Time was of the essence, so after a quicker-than-usual vetting process, we made a selection and got started. Please note: there is generally a lot of decision making that goes on in our vetting process. However, I’m simplifying the choice here in the interest of brevity.

Thoroughly vet communication

The project started smoothly enough, but things took a turn during our first round of review. It quickly became apparent that our freelancer’s ability to speak English (our native language) was not as strong as we’d first been led to believe. He responded to our initial requests with what must have been canned responses in which he or someone else had put together clear, concise answers that caused us to overestimate his ability. We commonly work with people who speak English with varying degrees of proficiency. Usually, this wouldn’t have been an issue. However, it was the quick presto-chango between expectation and reality that drew our first red-flag.

Setting and living up to expectations

For remote workers and those who hire them alike, setting and living up to expectation is key. In our example, as the project continued, we found rapidly that our freelancer’s skill set wasn’t as he’d purported. We had particular skills and requirements which had been described in great detail in our ask. However, in practice, it was clear this guy wasn’t the pro he’d claimed to be. Our second red-flag came when he delivered our project after the first round of revision. With thorough and detailed feedback in hand, our “expert” provided a second round that was a dramatic step backward from the first. And further, when prompted to fix it, he was at least honest in saying he couldn’t do anything more. That brings us to our third and final flag…

Beware of flakes

If I had a dollar for every time a client, business associate, friend, or family member told me a horror story about working with a contractor I’d have many, many dollars. We’ve been using remote freelancers as long as I can remember, so thankfully, we don’t run into situations like this very often. Nonetheless, we got bit this time. And despite our freelancers (finally) honest appraisal regarding his ability to fix the problems he’d created for us, he was out of here and we were in a pickle.

One reason this experience is so common is that when bringing someone in for a one-off job, you typically have little or no relationship to speak of with the provider. It’s purely transactional. I have money, and you have skills. Let’s trade. But this lack of real connection is the root of the problem. Without it, you are at the behest of a person you don’t know and relying wholly on them to meet and achieve expectations. There are tools in vetting you can use to hedge your bets (reviews, testimonials, past-projects, etc.), but ultimately you don’t really know.

Well, crap. What can I do to avoid a situation like this?

Understanding that these issues are somewhat unavoidable and recognizing that they occur to varying degrees is essential. Sometimes you’ll get lucky and get a great freelancer. God knows there are millions of them. But in an attempt to avoid the baddies, let's revisit the tools I've mentioned throughout for vetting your remote worker.

• Communication. Communication is critical. You must be able to communicate effectively with your remote worker to ensure that scope and project requirements are understood completely. Whenever possible, have a kickoff conversation in-person — or some digital equivalent — before commencing work. This will go a long way towards building the often overlooked interpersonal relationship with your remote prospect. Additionally, be sure that you are available and able to communicate with your worker using mutually agreed upon modalities. Conventional methods include email, Slack (or other instant messaging platforms), Google Docs, PDFs, etc.
• Say what you mean and act accordingly. The expectations you set for your contract worker need to be addressed clearly and in advance. There is always room for deception, as was described in my example. However, clarity in need, in addition to clarity regarding the means by which said need is to be accomplished, must be effectively communicated. Further, aspects of any given project, for example, timeline, milestones, deliverables, budget, etc., should all be discussed in advance and adhered to by both the buyer and seller.
• The back-up Plan. Responsible project planning should at a minimum, always include thoughts about a “plan B.” Knowing freelancers can be flakey, plan for resources to take over should the worst-case scenario be played out. This is especially critical when doing work for a client or any situation where crap will hit the proverbial fan if your resource goes radio silent.
• Reviews, testimonials, past-projects, oh my! Take time to review and use what information is available to you while interviewing your freelancer. Sites like Upwork.com feature several ways for their users to share testimonials, past-work, and reviews from previous clients. Of course, like everything in life, these safety mechanisms won’t entirely eliminate the kinds of issues I’ve described here—as is evident by the fact that we have this article. But minimally, they help reduce risk and give potential buyers a little peace of mind.

Ever been burned?

Of course you have. But what did you learn from your experiences, and how have you avoided subsequent drama? Any tools, tips, or hacks you’ve found particularly helpful in your experience hiring outside help? Share them here or find me on the socials and let’s continue this conversation wherever the audience most suited to hear it can get involved - I am @ryanroghaar here on Medium, Twitter, and Instagram and click here to for my LinkedIn.

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