Working with freelancers can be a super effective way to support any business. Or, it can be a waste of money and a terrible experience. It depends on your level of preparation and often, pure luck.
Who am I to tell you this? Over some 15 years, I’ve hired and worked with hundreds of freelancers. With some, we’ve worked on creatives: animation, billboards, TV ads and the like. I also managed a crazy number of digital products. Mobile apps, websites and portals, enterprise information systems, APIs, virtual reality, games. Any type and size of software product you can think of.
Anything from a budget of $10 to six big digits.
We’ve also helped companies build 100% remote organizations, all based on freelance talent. I personally believe that this is the future of work. And it’s a bright future as well. We just need to gain a little experience and caution to get it right.
The wild wild west
Freelancer portals can be intimidating at first. They are the wild wild west! When you browse through profiles, bad candidates can have excellent descriptions, while otherwise great freelancers might have terrible ones.
You’ll find honest errors and borderline scam. You may or may not be able to trust degrees, certificates and reviews. And even when you find someone truly wonderful, there’s a question you can’t answer from the profile alone. How could you tell whether they are a good fit for your idea and your management style?
The test of the pudding is in eating it
The old saying is 100% applicable here: the test of the pudding really is in eating it. Once you’ve shortlisted the top candidates, the next step would be to get started on the job. At least according to the job portals.
But, as in a romantic relationship: you should see if you can enjoy a short vacation first, and only then move in together with.
A small trial project is the best way to test the working relationship. You just don’t know what you don’t know. The trial project can discover red flags that you couldn’t possibly see on interviews.
And, as a hugely positive side effect, it can also confirm your own assumptions about the project. You’ll see whether your original timelines and guesstimates will be realistic going forward.
Choosing an appropriate project to start with
Don’t go far to choose the project: it should be a small, confined part of the main project. Perhaps one of its core features, but something that the freelancer can do within a week.
Mind you, it’s important to focus on a core feature first.
Developers, for example, have written the same login & signup mechanics many times. Todo list apps. Cameras. None of these would work well as a test project, because all they will do is to take an existing app off the selves. Or grab one from Github. You can’t test their speed nor ability, and more importantly, you don’t know how well they’d translate your ideas into code. Ask them to write a core feature. The calculator, the main interface, the business logic.
If you work with a copywriter, don’t ask them to write the first introduction chapter or a first few paragraphs of something. Rather, ask them to capture the essence of a story or the creative. You want to test real abilities with the trial project.
Even better if you can break the main project into milestones, and use the first milestone for the trial. Freelancers hate to look for a new gig every minute. So, if your project has a predictable scope of work and clear milestones, they will be happier to do a great job for you. Just make sure to pick a module that’s similar in complexity to the rest of the project.
The trial is a real job
The rule of doing any business is: always cap the downside. If you’re not completely happy working together, then all that’s lost should be a couple of days of work.
If the trial project is successful, the freelancer can move on to the next milestone right away. Soon, the project will be ready to roll on autopilot.
Every opportunity to work with a freelancer will make you a better project manager. Even if the project fails and you lose some cash, you’ll still have earned a super useful experience. You’ll be better at managing projects and spotting talent who fits your style the most.
A paid test project is a real job. It gives you a preview of how someone performs when they’re doing real work for you. It also helps you align the expectations and timelines for the rest of the project. Make trials part of your process, and your projects will be set up for success.
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