6 Signs You Shouldn’t Make That Freelancer Hire

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Internal hires are the best, right? Just click that little box in your applicant tracking system and it makes a world of difference. And having freelances is almost exactly like having an internal hire, isn’t it? You’re just taking on someone who already works for you in a new capacity!

Not quite.

Freelancing for a company is very different from a full-time position with the same company. (I say this as someone who’s done a lot of freelancing, in case you were wondering.) The challenges and demands are different, and while sometimes the fit is great, just assuming that a freelancer will fit right in is a mistake.

Here are six signs you should keep an eye out for if you’re wondering if your freelancer is a perfect match or a potential dud.

1. Deadlines are more of a vague suggestion for your freelancer hire

A huge problem that some employers have with freelancers is work coming in late. The reasons that a freelancer might run late are numerous. Maybe they’re bogged down with way too many clients, maybe your project took longer than their original estimate, or maybe their time management skills are lacking.

Whatever the reason, it’s a bad sign if a freelancer you’d like to hire full time is chronically late.

But there’s hope!

If you work with an often late (or even occasionally late) freelancer, talk to them about it. Avoid being accusatory or judge-y, at least in your tone or email text by being open and asking how you can work on this problem together, rather than blaming the freelancer right away. Try to find out if there’s a reason for the ongoing lateness. If they have too much on their plate, they may fare way better with only one dedicated employer instead of a slew of clients.

2. There’s too much back and forth

Every project is going to involve some degree of back and forth between freelancer and client. You’ll need to communicate to figure out the parameters and details of your project, and you may need to edit or tweak the freelancer’s work a bit.

“A bit” does not mean endless weeks of email chains and phone tag while you try to figure out every single detail of a project that should have taken two weeks, tops.

If your freelancer isn’t listening, is ignoring your commentary, or can’t seem to give you what you need no matter what you do, pause before working with them full time.

But there’s hope!

Look at the chats or emails you’ve been sending. Is it possible that the freelancer is the one holding up the process? Or is it possible that you haven’t been listening, understanding, or communicating clearly yourself?

We never want to think of ourselves as being in the wrong, but sometimes it happens. And if someone else knows a lot more about a topic than you do (and they do, that’s why you hired them, right?) it’s usually smart to take their advice.

Don’t be like these guys.

3. Their bandwidth is too narrow

A perpetually stressed-out, to-the-wire freelancer is a problem.

I hear you now: “But Halden, it’s not my problem!” And that’s fair. But if you hire that stressed-out freelancer, their bandwidth is going to become your problem.

You should watch out for a freelancer who has a narrow bandwidth for reasons that aren’t their job.

Many freelancers are full-time employees elsewhere using freelancing as a side gig, or are full-time students going for a degree. Those third-party obligations are probably going to come before you and your projects, even if you’re offering steady employment.

But there’s hope!

You don’t have to know exactly what’s going on in your freelancer’s life. And you may have no idea if they’re only able to take one project a month because of other projects for different clients or because they have a physics final due on Friday.

But if they’re stressed because they’re taking on too much work they, like the freelancer who’s always late, may actually benefit from steady single-source employment. Have a chat with them to find out what’s what.

4. You’ll only need them infrequently

Enough about their bandwidth; let’s talk about yours.

Have you considered why you’re hiring one of your freelancers? Is it because you think you can get the same work out of them but with more dedicated details, or because you want to have them on-call for you all the time? Or do you truly need someone in your office working on these projects every day?

If you don’t think you can create enough tasks for an in-house writer or designer or editor or whatever it is you have a freelancer doing, then don’t make the hire.

But there’s hope!

So maybe you do need a more dedicated focus on your project. Have you considered giving your freelancer more time and paying them more to prioritize your work?

As a former freelancer, I assure you that giving them advance notice and a bonus for the extra planning time will may a world of difference in the speed at which projects get completed.

Or maybe you need someone more frequently. Consider hiring the freelancer part time instead of full time, or hiring an additional freelancer and dividing the workload between them. Making a full time employee out of a single freelancer isn’t a panacea.

5. They’re a poor culture fit

Freelancers are great because they’re rarely or never in your office! No desk upkeep, no physical presence, and no way to know if they’ll fit in with your company culture.

Take a long, hard look at your company’s culture. Are you a traditional office where everyone shows up in pencil skirts and ties every day? A graphic designer with a ring through their septum might not be the best match. (And I say that as someone with a ring through her septum.) On the other side of the issue, if you’re a tech startup trying to launch out of a tiny rented office, will a hyper-formal freelance accountant gel with the rest of the team?

But there’s hope!

You can say stereotypes are there for a reason, but then you’d be ignoring how complex and multifaceted humans really are.

Appearances, from age to number of piercings, aren’t as important as personality when it comes to culture fit. A few long conversations with your freelancer about their work style and approach can tell you if they’ll be a seamless addition to your office staff. There’s a lot to be said for hiring blind!

6. You wouldn’t hire them if they’d applied the old-fashioned way

This is probably the most important sign on this list.

If your freelancer would never make it through your ATS or would bomb your interview process, you may want to think twice about hiring them full time.

Take a look at why you think they wouldn’t have done well if they’d applied traditionally. Is their resume lacking? Perhaps they have nothing but freelance experience right now, or maybe their academic record has a few scratches.

If it’s not their work history, perhaps your freelancer is painfully shy or reserved, or might come on way too strong and excitable, both qualities that can spell doom for an interview. If your intuition is telling you you’d never have hired them normally, listen to it.

But there’s hope!

Applicant tracking software is only as good as the humans that design it. If you’ve gone wrong in setting it up, it’s no wonder that the best candidates might get filtered out.

You may have contracted with your freelancer never imagining them in a formal office setting, but if they’ve done nothing but excellent work for you and you’ve never had a personality problem with them, who cares if they wouldn’t have cut it in a formal application process? They may be the perfect hire after all.

So should you make that freelancer hire?

You want to hire your freelancer. Heck, I want you to hire your freelancer! I hope you can and that everything works out for you both.

But if they showed any of these signs, you may want to think twice before starting salary negotiations. Sometimes, people are just better suited where they are, and that’s ok. It’s up to you to determine if the hire is a right fit, so watch for these tells.

Looking for Talent Management software? Check out Capterra's list of the best Talent Management software solutions.

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About the Author


Halden Ingwersen

Halden Ingwersen is a former Capterra analyst.


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