How to Hire Feelancers on UpWork So You Can Relax

You saw an advertisement for UpWork on YouTube that gave you the bright idea to hire a freelancer to do your work for you. You think hiring a freelancer is fun and easy, and you can’t wait to relax more now that someone is working for you. WRONG, think again.

Maybe you’ve even tried hiring freelancers on UpWork, but it didn’t quite go as planned. Check out these tips for hiring freelancers and managing projects remotely.

Enter Procrastination Man

It was late, and my to-do list wasn’t getting any smaller. I had been up late the previous night working on a deadline coming up, but I wasn’t even close to finishing. I remember early in my career, I would dream of the day where I could find enough work to sustain myself, but now I have a much different problem; I can’t get the work done fast enough! I’ve heard people say things like, “If you want to grow, hire more help.” So, I thought I’d give it a shot, but it turned out different than I anticipated.

For some reason, I assumed that every freelancer I spoke to would possess the necessary amount of drive/motivation/technical capability to solve problems according to project requirements/guidelines that I’ve provided. That’s what I do for my clients, and usually everything runs smoothly.

I listen intently, take notes during a “discovery” phase, write project requirements, plan/design, and then execute. It’s a pretty straightforward process that always results in a solution and a happy customer. However, finding someone like me has proved to be very difficult, unfortunately, and now I can see why so many clients have told me they were happy to find me. That’s because I’m very responsive, pay close attention to detail, and I always deliver what is expected of me – surprisingly, this is not something you will find in every freelancer you talk to.

Hire a freelancer they said… it will help you they said…

In only a few weeks of managing a team of freelancers, I’ve had to fire two of them for misrepresenting their skills and not moving forward quickly enough. One of the guys I fired would say “yes” to everything I said, and eventually I learned the hard way that he wasn’t a good fit, effectively wasting about 3 weeks of time and several hours. It was rather infuriating, mainly because when I hired this particular freelancer I asked him could he do it repeatedly (because I had my doubts), and he assured me that it would be no problem. Eventually, I just didn’t see the results I wanted and got tired of waiting around. I expected this to go a little more smoothly. It seems simple, right? Just hire someone to do your work for you, but it’s definitely not that simple.

Don’t get me wrong, I’ve even told clients “I can do that” when I wasn’t exactly sure how, but I’ve never had to go back to a client and tell them I couldn’t do it, or even worse, have the client remove me from the project because of poor performance. If he had come to me, and let me know that the project was over his head and he would be better suited on a different project – then, I would have been much happier and perhaps maybe would have even reassigned him to a more suitable task. So, if you are a freelancer reading this, remember that transparency and communication are key. If you are going to miss a deadline, or you are having some trouble then let the client know sooner than later. Trust me, it’s infinitely better to tell the client as soon as you can if you are unable to do the work or if something comes up, don’t wait until the day of. If your freelancer pulls this sort of thing regularly, it may be time to find a replacement.

Story Time with Anthony

Now, back to my story… In terms of management, I knew exactly what they needed to succeed because I’m a developer myself. I wanted to minimize the amount of snags or hangups, so I made sure not to leave any stones unturned. I wanted consistent execution until the project was complete, and in my experience that is much easier when you have all the necessary documentation and assets from the very beginning.

I provided several in-depth videos explaining project scope, ideas for solutions to some of the problems within the project, instructions for using git, etc. I also provided very detailed instructions, project requirements and guidelines, and I loaded all tasks into Asana so that my team could easily review assignments and it’s details. Despite me going out of my way to ensure my freelancers had detailed instructions, I was still very disappointed by their efforts (or lack thereof)

Where did I go wrong?

“How could they fail with everything they needed to succeed?” I thought to myself, while sitting in my office trying to figure out where it all went wrong. I know my instructions were clear and very detailed, but what did I do wrong? Something certainly could have been done to prevent this, but what was it? Then, it occurred to me. This all could have been avoided if I had vetted the candidates properly and defined the tasks and project guidelines more clearly. I provided instructions, but I didn’t clearly define every little thing – but you have to!

When vetting candidates here are a few things to consider:

First off, you can’t work with people you can’t connect with. If your freelancer is unwilling to get on a phone call with you, or you can’t really communicate with them – how will you work together to overcome challenges? (Freelancers: this goes for clients too!)

Secondly, let’s not forget about how many people want to learn how to code and are trying to get into the field but aren’t actually prepared to deliver work for your clients. Everyone says that they are a programmer, but the sphere of software development is massive. Writing simple programs that display”Hello World!” doesn’t prepare you for solving real world problems with software design.

College Daze

I’ll never forget one of my favorite Computer Science professors, Dr. Sauls, reminding us of this sentiment regularly: “There are a lot of copy/paste programmers in the world”, and then she would explain to us the importance of learning the vocabulary, the fundamentals, best practices and modern standards, etc. This was her go to response whenever we complained about her teaching us the “boring” parts of software design.

After nearly a decade in the industry, I realize that she wasn’t kidding around and I’m grateful for my formal background in software design because learning how to write code isn’t enough. You need to hire someone that can do more than write code with the correct syntax, that’s something you can learn in a few hours, or days, depending on the language.

The Bottom Line

So, let’s recap… To hire a good freelancer you need to:

  • Interview as many candidates as possible: I prefer video interviews to gauge personality and soft skills.
  • Don’t hire someone because you need the work done badly. In order for the work to get done right, you’ll have to find the right person and that may take some time.
  • That brings me to my next point: Be patient! You may not find the perfect fit during the first round of interviews but don’t give up and/or settle for a candidate that’s less than qualified.
  • Hiring intrinsically carries a lot of risk. You must hire SMART. Why? Because hiring costs a lot of money, that is why you have to go through multiple rounds of interviews when getting a full-time job.
  • Be thorough when vetting candidates: check their portfolio, review their source code, ask questions about their capabilities, and prior work experience. If they are talented and capable, it will show in their portfolio. If they have a bad portfolio, they will probably deliver bad work. If they don’t have a portfolio, don’t judge them right away but if they can’t show you some of the projects they’ve worked on then you aren’t talking to a freelancer, that seems more like an intern.
  • Interns aren’t necessarily bad, but you don’t want to pay an intern the same rate that you would pay a specialist. You’re trying to hire a specialist unless the task is very simple, then an intern may workout fine, actually. I’ve never hired an intern, but it seems like a good deal for all parties involved.
  • Documentation, documentation, documentation: You can never provide too many details.  You can, however, provide to little details – don’t do that.
  • If you give requirements without guidelines, then your freelancer may steer way off course. Don’t micromanage, but you must guide the project through all the stages of the software development life cycle.
  • If you give guidelines with no requirements, then you will end up with features you didn’t ask for because the developer thought it was “cool” or something. It’s important that your instructions are followed, and that developers stay within the scope of the project.
  • Watch out for “red flags” like weird excuses, no portfolio, saying they understand but it seems like they don’t, only working ~1-2 hours at a time, working less than 3 hours a day, etc. All of these are warning signs of a bad freelancing experience. Listen to your gut instinct. If you have a bad feeling about it, there is probably a good reason for it. After all, no one ever says “I shouldn’t have listened to my gut instinct”… Right??

I hope the information in this article proves to be useful for you, and as always thank for reading. Try to continue the conversation on your own, and apply what you’ve learned here. Ask yourself questions like: What kind of traits do you look for when hiring freelancers? What kind of traits do you avoid, or would consider “red flags”?

Have something to say about this article? I’d love to hear your thoughts in the comments below! Thanks again for reading, catch you on the flip side!

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