How to help freelancers make the transition to being full-time employees

Kelly K. James had been a successful freelance writer for more than two decades. But, as a single mom with two teenage children, a growing health insurance bill, and looming college tuition, the pressures of freelancing’s ebb-and-flow income patterns were stressful. James, on a whim, decided to apply for a full-time job.

James landed the job and has remained part of the W2-form-receiving crowd ever since, even writing a memoir about the experience, entitled The Book that (Almost) Got Me Fired: How I (Barely) Survived a Year in Corporate America. But it hasn’t been without its adjustments.“One of the hardest parts was having to sit at a desk all day. When I was working at home, I’d also get out a lot to walk the dog or run an errand,” she recalls.

The strength of freelancers

The number of U.S. workers employed as independent contractors has grown. Jobs platform Upwork estimates freelancers comprise 38% of the U.S. workforce. However, like James, the lure of a steady paycheck, paid time off, and benefits such as health insurance and an employer-sponsored retirement plan can be strong motivators to rejoin the 9-to-5 crowd.

For employers and managers, freelancers bring some distinct skills and advantages that may not be as well-honed in people who haven’t worked for themselves—but you also have to know how to manage them, says workplace expert and career coach Diane Rosen, founder of DR Squared Consultants, a workplace and HR consultancy.

“The employee is used to working on their own schedule and with contractual parameters for the assignment . . . ” Rosen says. “[Becoming a full-time worker] may alter the nature and dynamic of the relationship for the employee who will now be on a different schedule, must follow company HR protocols, may have less autonomy or flexibility, and may have to deal with hierarchies that were avoided as a freelancer.”

However, some best practices can help you ease the transition for freelancers returning to full-time employment and help you reap the rewards of self-starters who were able to make it on their own—at least for a while.

Don’t forego onboarding and training

Three years ago, Rachel Sklar was hired as a vice president at membership club SaksWorks. She says there was no formal onboarding in the rush to get her up and running. And while she was a skilled and experienced executive and entrepreneur, shared calendars were a new experience. “I was completely confused by meetings just popping up on my calendar out of nowhere without any actual invitation,” and she missed a few because she didn’t understand the tool.

“This extreme basic of corporate America was so foreign to me, a person who had founded, built, run, and sold a company built on Google Groups,” she says. She says the upshot is to make sure your team has used the tools you rely on and to onboard them as you would other employees.

Assess their skill sets

Similarly, Rosen says that former freelancers may have high-level experience in doing the work, but may not have experience managing a team or large budget, for example. “It’s very different to be the expert in something versus being the boss,” she says. So, you’ll need to understand where they need upskilling or additional support and development and be prepared to provide that.

Understand their work style

When you freelance full time, you often have more control over your time and how you structure your work than if you work as an employee in the office. And freelancers may learn to be efficient with their time, as they not only have to do their work, but they have to find clients and run the administrative needs of their business, including invoicing, marketing, administrative work, etc., says Wendy Hanson, cofounder and chief of culture and community at coaching and training platform New Level Work.

Hanson says it’s important to get to know the individual’s work style. How do they like to communicate? How much autonomy and flexibility do they need? What is their process for approaching the work? “Freelancers work differently, and you need to know their style,” she says. Doing so will help you create the structure they need to thrive.

James agrees. “The number-one thing you need to know about most freelancers is that they have the ability to get work done without needing to be micromanaged. Freelancers can only succeed in their businesses if they are able to multitask, manage their time well, figure out ways to solve problems on their own, and work with a variety of different types of people in different organizational settings and with different kinds of content and subject areas,” James says. Get to know what they need to deliver those strengths to benefit your business.

Agree on ground rules and a feedback process

Hanson says it’s important to find the balance between checking in regularly—necessary to help manage the transition from freelance to full-time—and not make the individual feel micromanaged. Share clear expectations about work hours, communication-response times, and other business-culture norms at your company. Find out how they prefer to receive feedback and set some ground rules for delivering that feedback regularly.

Hanson suggests one-on-one meetings weekly, at first, just to check in. After the first couple of months, the meetings may be less frequent. She also suggests pairing your new employee with a mentor to help show them the ropes.

Listen to their contributions

By nature, freelancers are problem-solvers with more insight into the big picture of running a business. Take time during your meetings to encourage suggestions and feedback, Hanson says. Your new team member may have ideas about how to do things better or more efficiently.

Help them get comfortable sharing ideas in meetings and provide professional development programs or coaching to help them continue to grow. “Be patient as they adjust and celebrate their freelance learnings and experience,” she says.

The transition from freelance to full-time may hold some challenges. However, trying to understand and overcome them can help you develop a valuable team member.