How To Hire And Manage Freelance Professionals

Freelancers now comprise over one-third of the American workforce: Here’s how to work with them.

How To Hire And Manage Freelance Professionals
[Photo: Flickr user University of Michigan School of Natural Resources & Environment]

Even if you’ve never worked with a freelancer in the past, chances are you will pretty soon.


Freelance professionals can be found in nearly every corner of the country and in nearly every industry. This cohort of independent American workers is now 55 million strong–an increase over the 54 million who reported freelancing in 2015. That comprises approximately 35% of the entire country’s workforce, according to a recent independent workforce study by the Freelancers Union and Upwork.

Working with a freelancer requires unique considerations distinct from typical employees or a typical vendor. Whether it’s finding, vetting, and onboarding a freelancer, maintaining clear expectations, or having a process for conflict resolution, there are certain considerations employers need to maintain when working with a freelance professional.

How To Find And Vet Freelance Professionals

While there are a number of online resources and databases containing freelancer profiles and portfolios, those should only act as a starting point, explains Rachel Zimmer, the cofounder of 5Crowd, a two-sided marketplace that connects freelance professionals in 150 cities around the world with Fortune 500 companies.

“It’s really important to do your homework when vetting an individual, and vetting an individual goes so much beyond just their portfolio,” she says. Zimmer adds that while online portfolios can be a strong indicator of the freelance professional’s quality of work, certain intangible yet equally important elements, such as how they respond to feedback, whether they have long-term potential, and whether they deliver on time, can only be discovered through a more thorough vetting process.

Zimmer explains that 5Crowd typically puts its freelance professionals through a brief paid pilot project to “test the waters” before diving in with a longer-term contract.

“Whether it’s the portfolio or email correspondence, all the way through to the pilot project, those are all pieces that we use to vet for a whole bunch of different criteria based on the required skill set,” she says.


Communication Is Key

Communication is a key consideration in any business, but it becomes especially important when working with freelancers, particularly those who work remotely. Maintaining clear expectations and milestones, invoicing and payment procedures, and timelines for deliverables can help prevent disputes between freelancers and their employers later on.

“The more each party can share up front, the smoother sailing it will be,” says Zimmer. “Set expectations from an employer perspective on how fast you’re going to pay someone, and what is required up front,” she says. “From the freelancer’s perspective, make sure you set expectations on what you’re going to deliver and how you’re going to deliver it,” Zimmer adds.

It’s also important for employers to share the institutional knowledge they retain on the specific project or client with the temporary staff they’re onboarding for that project.

“It’s important to provide context in order to get the best work and the best results,” says James Loftus, the vice president of strategic communications for CO-OP Advertising, a Toronto-based full-service creative agency that employs up to 40 freelancers on a regular basis.

“Remember that freelancers haven’t been living and breathing your client for the last year or more like you have, so it’s important to frame up the project or the challenge that’s ahead of them,” he says. “Take the time to do that instead of just sending off a quick email saying, ‘I need your help.’”

Pay Your Freelancers On Time

Freelance employers have a tendency to treat their temporary staff like any other large vendor, providing payments on a 60- to 90-day cycle. However, research has shown that the primary concern among freelance professionals is receiving payment in a timely fashion.


“We know from our research that this is a problem that affects seven out of 10 freelancers,” says Caitlin Pearce, the director of member engagement for the Freelancers Union. “That’s my number one piece of advice: pay your freelancers on time,” she maintains.

Just as employers carefully vet their freelance partners, explains Pearce, freelancers often vet their employers, both within their personal networks and online. Not paying a freelancer on time or at all can therefore lead to a negative relationship with the freelance community at large, and make it difficult to find qualified independent workers in the future.

Show Freelancers The Love

While freelancers are not full-time employees, Pearce emphasizes that it is important for employers to treat them with the same level of respect that they would any other team member.

“Remember to include your freelancers in your social events,” says Pearce, such as holiday parties and other gatherings. Pearce says this way they can continue to make the connections that employees make, “which will ensure great working relationships.”

5Crowd, for its part, publishes a Freelancer Spotlight video blog highlighting the life and work of its freelancer community around the globe, while CO-OP Advertising hosts a quarterly meetup group to discuss trends in the freelance advertising industry. CO-OP also recently announced the Freelancers Unite awards, providing employers from across Canada the opportunity to nominate their creative freelancers.

“The meetups and the awards are opportunities [for freelancers] to not only engage with the organization as more than just a solution for a particular timeframe,” says Loftus, “but also to actually bring them into the fold of the cultural organization, which is key.” Loftus says that the Freelancers Unite awards will extend to the U.S. next year.


“Treating freelancers like they are members of your own staff is a guiding principal that we use day in, day out,” says Loftus. He believes that doing so is vital for maintaining long-lasting relationships with individual freelancers as well as establishing a positive reputation in the freelance community at large.


About the author

Jared Lindzon is a freelance journalist and public speaker born, raised and based in Toronto, Canada. Lindzon's writing focuses on the future of work and talent as it relates to technological innovation, as well as entrepreneurship, technology, politics, sports and music.