Should you include freelancers in your talent development program?

Increasingly, contract workers are integrated into teams. It may make sense to invest in developing them, too.

Should you include freelancers in your talent development program?
[Photo: Christina Morillo/Pexels]

Freelancing is on the rise–and so is integration of freelancers into organizational teams. The “2018 Future Workforce” report from freelancing website Upwork, released in February, found that 59% of hiring managers are using flexible talent–freelancers, temporary, and agency workers–which is more than double the 2017 percentage (24%).


At the same time, Americans have embraced freelancing as a career choice. Upwork’s “Freelancing in 2018” report, released on October 31, 2018, found that 3.7 million more people began freelancing between 2014 and 2018. The report also found that freelancers place more value on skills training. The U.S. freelance workforce is growing faster than the overall U.S. workforce, outpacing overall U.S. workforce growth at a rate three times faster since 2014. Upwork’s report predicts that the workforce will be majority freelance by 2027.

Winning the Freelance Talent Wars

While it may seem counterintuitive to invest training resources in people who are not employees, the lines between W2 workers and 1099 workers can be blurry sometimes. As freelancers take on new responsibilities in your organization, it may be time to consider investing in them, says Mike Boro, a partner in PwC’s Workforce of the Future practice. “I do think there is a war for talent, there is a war for independent contractors, so the better you can do to get your independent contractors integrated and then learning something which advances their skill set is actually a positive as well,” he says.

And freelancers are likely to welcome those opportunities. Seventy percent of full-time freelancers participated in skills training in the past six months compared to only 49% of full-time non-freelancers.

Kari DePhillips, owner of digital marketing firm The Content Factory, integrates a period of freelancing and training into her hiring process. If she’s interested in hiring a candidate, she’ll hire them as an independent contractor and pay an hourly rate for them to complete several of her company’s extensive online training modules. After a 60- to 90- day trial period, if she’s satisfied with the training results, she hires the employee. This leads to very little turnover, as she and her employees have already had a “trial run,” and she has the added assurance that the people she’s onboarding have the skills her clients need, she says.

Creating Criteria

To train or not to train depends on the duration of the contractor’s tenure and the role they’ll play, says Diane Domeyer, executive director of The Creative Group, a division of staffing firm Robert Half that works with creative agencies. “It depends on the duration of that contractor’s tenure or anticipated tenure with your organization. It starts with especially if it is a longer-term freelancer or contractor, they will be even more valuable to your organization if you provide them first and foremost training on your company,” she says.


From there, you have some decisions to make, Boro says. It’s also a good idea to train contract workers who are integrated into your teams in the same onboarding training that your employees receive. This may include the compliance-related areas in which your employees are trained, such as sexual harassment and any other code of conduct training, as well as an introduction to your brand and its standards, processes, tools, and systems, etc. That training helps set up your contractor for success, he says. One employer he knows allows employees and contractors access to training materials before they’re formally “in the system.” As a result, they can access the training before they’re officially brought on board and hit the ground running once they start working with the company.

From there, you need a good understanding of the roles these workers are playing within your organization, Domeyer says. If they’re completing defined tasks and don’t have client interaction, then you may not need to invest in more training. However, highly skilled freelancers might end up taking on more responsibility, in which case it may be wise to invest in the same soft skills and leadership training you’re giving your employees, especially if they will have client contact or important roles on key teams.

Reaping the Rewards

March 2018 research by Robert Half discovered the top challenges advertising and marketing executives have when working with creative freelancers. They included:

  • Making them feel like part of the team: 25%
  • Negotiating pay rates: 22%
  • Communicating or collaborating effectively with them: 19%

Strategic training could help overcome at least two of those issues–integrating them into the team and communicating and collaborating more effectively. Domeyer points out that many companies don’t invest enough in training overall, but that it can help teams overcome key challenges in attracting and retaining high-level freelance talent. “Simply by opening access to your freelancers, you can give them exposure to some of the skills-based training or soft-skills training without a lot of incremental expense,” she says. Boro adds that if contractors are valuable enough to be trained, they should also be compensated for that training time.

More people are working freelance because it gives them control, diversity of work, and allows them to keep their skills current and fresh, Domeyer says. “Take advantage of what you have for your existing employees and loop them in, especially if it’s an in-demand skill set, because that’s what professionals are looking for,” she says “Since there’s a diminishing supply of top talent and increasing demand, to the extent that you can include in the training your freelancers or contractors, you’re more apt to be able to move them from project to project and build upon the value as they learn about your company and are able to be that much more effective.”

About the author

Gwen Moran is a writer, editor, and creator of Bloom Anywhere, a website for people who want to move up or move on. She writes about business, leadership, money, and assorted other topics for leading publications and websites