Top 3 Problems When Hiring Freelancers (and how to solve them)

I’ve been in freelancing web-development world for about 10 years — both being hired and hiring. And, boy, I’ve seen a lot of failures on both ends. Quite often companies are even afraid of hiring remote help, because of past mediocre (to say the least) experience with outsourcing. So let’s talk about some myths and truths — who are these people called “freelancers”, how they think and how to deal with them effectively?

Problem 1. Choosing a freelancer is painful.

Usually when people need external help, they post an ad on job boards like Upwork or Freelancer. And then get bombarded by dozens of contest participants who all seem to present themselves in a professional manner. How to choose? Not even that, how to find time to read all those quotes and introductions? Panic mode, huh?

Relax, it’s not that bad. 
Here are some tips to eliminate some candidates on the spot:

  1. If the offer is sent only 5 minutes after you post a job. It usually means two things: they copy-pasted their text and probably didn’t even read your job description. And in general, I find difficult to trust people who play that “speed” game too obviously.
  2. Similar: if the offer is clearly copy-pasted. You can easily sense an advertisement tone from a mile these days. More and more I see job descriptions which end like “Please start your offer with words ‘Star Wars’ (just as an example) to prove that you have actually read this”. That means something — those copy-pasters need some kind of filter.
  3. If they are selling THEIR services, not solution to YOUR problem. If the offer says hundred words about how great and professional freelancer is but doesn’t say a word about your particular project, again it usually means that they didn’t bother reading it all. Or, worse, they don’t care about your project — they just care about getting job/money.
  4. If you get a short answer and non-detailed quote. If you read something like “I can do this job for $500” (whatever the amount is), that means the person didn’t bother to prepare a detailed explanation of why it costs that much or what exactly will be done for this amount. Usually it means they try to save time on preparing the offer. Which often leads to saving time on doing the job as well. Professional candidates tend to send less offers but for jobs they particularly fit for.

Ok, so these are four disqualifiers to take on board. With these you can safely turn down 50% or more of the offers, but there are still a handful of candidates to choose from. Who tend to perform better and how to sense the best of the best?

  1. Proven track record and past projects. Usually freelance job boards show history of candidates, with ratings, feedback or sometimes even prices of work. Look for five-star reviews and happy clients before you. Now, keep in mind that there are new freelancers who don’t have ratings yet and they MIGHT be a good fit — but then ask them for some testimonials or work examples from outside the job board.
  2. Understandable language. You would think that for a web-developer perfect English is not really an important thing, right? Wrong. If you are a freelancer, you have to express your thoughts freely and communicate with a client without any barriers. So if you, as a client, sense that their offer lacks clarity of language in the offer, that could be a red flag during project itself. And I’m not talking about grammar, a few typos and missed commas here and there are actually OK, I mean that you have to understand the text easily and don’t have to spend extra time on “translating” it in your mind.
  3. Right questions and suggestions. If freelancers want to invest their time in your project, they would ask some questions — not only to clarify the task, but to understand the ultimate goal of your business. If you need a website, you actually don’t need a *website*, your goal is probably to sell more stuff, website is just means to do it. Next level — after asking the right questions, a professional would suggest an alternative way to achieve goals or maybe even would offer to withdraw some functionality as unnecessary, therefore saving your time/money.
  4. Talking about project first and only then about the money. It might sound silly, but money should be the outcome and the reward for the professional work, not the price for the time. So a reliable freelancer would first talk about the project and your goals and only then evaluate the final cost. And be prepared that the first quote might change quite significantly after more details come up.

So here are the tips on how to choose a freelancer from dozens of candidates. Now, second problem is related to actually working with them.

Problem 2. They are unpredictable.

Seems that most freelancers are selfish, lazy bastards who tend to work whenever they want, not when you need them. Which is partly true. Quite often projects go like this:
- You hire a freelancer, yay
- Both parties are excited to work on interesting project
- Somewhere in the middle you face first serious challenges/disagreements
- Freelancer gets a little demotivated to work further
- They get invited to more interesting/profitable project
- Shiny object syndrome (or simply a squirrel)— and they’re gone. Not answering emails, not picking up phone, ignoring Skype etc.
- Basically, you’re doomed.

Sounds familiar? Let’s think WHY this is happening. Couple reasons:

  1. Freelancers often think they are free to work whenever they feel like working. Otherwise, why freelance?
  2. Freelancers are often over-optimistic about project estimates and how much they can actually get done. To be fair, all people are bad at time estimates.
  3. More experienced freelancers realize that they are valuable asset and therefore become “divas” — which means you have to constantly motivate/ask/convince them to actually do the work.

Now, let’s think about what we can do with it.

  1. Agree on all the terms before starting the work — how much time per day is needed, what will be a communication channel (at least weekly), what are clear deliverables, milestones etc. In essence, the less freedom of thoughts you leave, the more chance of actually productive work.
  2. Be realistic about estimates yourself. If you want to build another Facebook in a week — I have good and bad news for you. Good news — you will find freelancers who will promise to deliver. Seriously. Bad news — they won’t. As it is said, “nine women can’t make a baby in one month”.
  3. Constantly communicate and don’t disappear. Always ask “how’s it going”, make it a habit to participate in the project — give feedback, quickly respond to questions and be visible. A client who gives the task and then disappears for a week is one of the worst motivators ever. And it’s not about the money — freelancers want to feel valuable and heard.
  4. After all, it is about the money. Let’s be completely honest. If you are looking for the cheapest work force — again, you will find them. And then you will be looking for more expensive people to fix their work, or even to do it from scratch. Sure, there is some brilliant talent in Middle East countries, but even there the most valuable ones don’t work for 10 $/hour. You get what you pay for.

Right, so we’ve touched on 2 problems already — how to hire and how to work with freelancers. And here’s the third and final one.

Problem 3. They are terrible at FINISHING.

Have you heard about a 90–10 rule of software development? It says: “The first 90 percent of the code accounts for the first 10 percent of the development time. The remaining 10 percent of the code accounts for the other 90 percent of the development time”.

Actually, this rule can be applied not only to this industry, but to the most of longer-term projects, especially with remote freelancers. But before blaming the other party, look at the reasons why delays happen:

  1. Lack of exact scope upfront. As I’ve mentioned before, you have to deal with all the details before starting the work — if you think that you just need to start and then discuss the details along the way, then you will never reach the finish line. Moreover, there’s a good chance of re-doing the project because of wrong strategy at the beginning. So the blame here is on both sides — on a lazy client (yes, you) for not spending time on preparing the scope/spec, and on a freelancer who didn’t raise correct questions.
  2. Lack of communication during the project. That goes back to some thoughts above, but the thing is that you have to constantly discuss milestones and progress, at least once a week, if not daily. And more professional freelancers will give the updates themselves, without you constantly asking or chasing them. The way I work, for example, is constantly thinking: “If a client is first asking me how are things going, it means that I don’t communicate enough/properly”.
  3. Not clear final goals. When does a freelancer get paid? When the project is done, right? But the problem is that DONE can be understood really differently by parties — for example in web-dev world, deliverable might be code pushed to the repository, project deployed to the server, project launched completely live etc. These are all similar but slightly different stages, so if you both don’t have a clear understanding what the FINISH is, you will hardly reach it.
  4. Lack of competence. This is a really hard one to spot until it’s too late. It seems that the project is going smoothly, until you reach final stages and then a freelancer has problems with deploying everything, setting it up on your server, making it all work without bugs etc. It usually means lack of real-life experience with bigger projects or in that particular area. There’s nothing more to comment here — the only cure here is not hire such a freelancer in the first place. By this stage you would have to hire additional help to finalize the things.

As you probably noticed, 3 out of 4 problems are mutual for both sides, and you can solve them at least partly, so do your best to help them finish the work. Yes, as a client, you are also required to work. Sometimes pretty hard.

Conclusion — so what should you do as a client?

To summarize those all thoughts into several main points, what you can do when hiring a freelancer:

  1. Take your time to choose the right candidate — quick hire is rarely a success.
  2. Have realistic expectations — about money, time and deadlines.
  3. Have a clear final goal — what you want to achieve and when you are happy with the result.
  4. Be involved — prepare task description properly, communicate constantly, give feedback.

I hope that these thoughts will help you to find, hire and manage freelancers more effectively, if you have any more questions or comments — hit me on Twitter or by email

One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.