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8 Questions To Ask Yourself Before Hiring A Freelancer

September 10, 2011

From American Express OPEN ForumQuestions to ask yourself before hiring a freelancer

By Katie Morell – Contributor, OPEN Forum Editors

Original Post-Sept. 8, 2011

If today’s struggling job market has produced anything positive, it’s an influx of highly qualified freelance workers. This is a win-win situation—great for the small business owner who needs help and can’t pay overhead costs, and favorable for the job seeker who needs a few extra bucks while searching for their next full-time gig.

These situations can also turn ugly, though, if a good match is not made between company and contract worker, so it’s important for small business owners to go in with their eyes wide open. Here are a few questions to ask yourself before handing over a contract.

1. Can you delegate?

No one likes to be micromanaged, so before you post an ad on Craigslist, consider which tasks you are comfortable delegating, suggests Carolann Jacobs, founder and president of Vivid Epiphany, a business coaching consultancy based in Plano, Texas.

“Only delegate what you can really let go, if you can’t delegate, the relationship isn’t going to work,” she says.

2. Have you outlined the job description in meticulous detail?

Whenever Logan Hale hires a freelancer, he dumbs down desired job tasks to an almost fifth grade level—and not because he assumes his hired help will have the I.Q. of a 10-year-old.

“I write things out in black and white and am clear about the objective of each task because I don’t want there to be any confusion; being vague is deadly,” says Hale, founder of YourLittleFilm, a Los Angeles, California-based business that produces films for families and small businesses.

3. What are the labor laws in your state?

This is a tricky one that can come back to bite you. Some states don’t allow employers to set specific hours for freelancers. Others require you to pay payroll taxes if a contract worker is based in your office.

“This is one of the most important things to know; many people hire contractors to avoid paying payroll taxes and benefits but then break the law in the management of them,” says Dylan Whitman, co-founder of Flank Digital, a digital marketing agency based in San Diego, California.

4. Will you check references?

While this may seem obvious, it is an easy step to bypass especially if you are in a rush for some help.

“Instead of checking references, a lot of people will just go on oDesk, read a couple reviews, hire someone based on those reviews, and then have a bad experience,” says Whitman.

5. Are you prepared to communicate daily?

Yep, daily—in no way does this reflect negatively on the competence of the contract worker. Instead, it shows that you are invested in their success.

“If a freelancer has a question, make sure to get back to them in a timely manner; communication is essential when managing this relationship—make sure you are a participant in the process; if you step away and don’t make yourself available, resentment can build,” says Jacobs.

6. What is your termination policy?

It’s easy to keep an underperformer on too long—you don’t want to hurt feelings, you may feel too busy to deal with the situation—so before hiring someone, write out your desired result metrics and prepare yourself to act on them, suggests Jacobs.

“If things aren’t working out, don’t wait. Sit them down for a frank conversation about how the arrangement can no longer move forward—just make sure to do it in a neutral tone, not when you are angry or resentful,” she says.

7. Are you prepared to pay a competitive rate?

Before posting a contract job, do some research on pay rates for various skill sets. This will help you easily weed out the highest and lowest bidders, says Whitman.

“Be wary of people who are too inexpensive because you may end up paying a lot more in the long run when you have to hire someone else; instead, go for someone whose prices are in the middle of the road,” he recommends. 

8. Are you ready to build your ‘bench’?

Hale believes it’s vital to have a “deep bench” of freelancers—one who may operate as your main go-to, and two or three others that can take on smaller projects when needed.

“You don’t want to find yourself scrambling if you get an influx of work; having a deep bench helps keep you in the power position of asking for help from a number of freelancers you trust,” he says.

Image: digitalart /

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