Managing an independent contractor or freelancer isn't like managing a full-time employee. You may never see each other face to face. This may be the first time you've worked together, or you may work together on a regular basis. Whatever the case may be, the situation comes with different management challenges. Here are the dos and don'ts.


1. Don't be a micromanager.

Especially if your freelancer is working off-site, you may be tempted to manage every step of the process. What is she doing anyway? For all you know, she's charging you $300 an hour to watch TV and eat chocolate frozen yogurt. The fact of the matter is you don't know what she's doing, and you can't control it. Hired guns don't necessarily work like your other employees. They may work all-nighters, in spurts, or do everything in the last couple of days. If you've done your research and found a great freelancer, you have to trust she will get the job done—by any means necessary.

2. Don't be a dictator.

The relationship between an employer and an independent contractor is a particularly symbiotic one. You didn't have an employee to handle the project at hand, so you've had to hire someone outside your business to do it. This means that while this person is working for you, it's a bit more like he's a paid, lone wolf consultant than one more person who does your bidding day in and day out. Therefore, it's important that you listen to what he is telling you about this project and how best to do it. He's the expert. Tune into his creative solutions, and you may find yourself with a better product than what you thought you wanted.

3. Don't be a harpy.

One of the most nerve-wracking aspects of working with an independent contractor is meeting deadlines. Still, regularly checking in with high-pressure tactics—i.e., sending hourly emails asking, "Is it done yet?"—means your contractor is spending all of her time—and some of your money—babysitting you and not meeting the deadline.


1. Nail down your work process before the project gets going.

You shouldn't be reinventing the wheel every time you hire a freelancer. Have a phone consultation, agree on the terms, the project, and the deadline, and settle on the amount and method of payment. If you want to have regular meetings as the project progresses, set those up at the beginning. If there may be cost changes along the way, discuss that upfront. If you'd like to see how it's going along the way, create a shared calendar to stay on the same page. Talking through all the possibilities upfront will anticipate most problems before they happen.

2. Pay on time.

One of the great agonies of being a hired gun—and I've been one for over 10 years—is getting paid. It's as if employers think that because you're not on their regular payroll, they can pay you however and whenever. In addition to settling on the fee, decide when and how invoices will be submitted, as well as when your freelancer can expect payment.

3. Trust her vision

Especially if your contractor is a creative—say, a graphic designer or a writer—you are going to go out on a limb together. You may see drafts at an early stage or similar work that this creative has done for other companies, but art and prose are not the same thing as coding and accounting. Have faith in your knowledge that you hired the right person and that her creative mind will bring to life the vision in your head.