As more freelancers enter the job force, managing them is an art form in and of itself. Here are the secrets to managing independent workers.

I’ve been a freelancer for more than 15 years. Here’s what all clients should know

For the past several years, there has been a steady stream of research indicating that companies are increasingly turning to freelance labor to fill talent gaps and create more flexible teams. Recent research from freelance website Upwork found reports that more than one in three Americans freelanced in 2018, and the freelance workforce grew 7% from 53 million to 56.7 million in five years. Full-time freelancers make up more than one-quarter (28%) of freelancers—up 11% since 2014.

And while hiring specific, on-demand talent may seem like a perfect solution to gaps in your workforce, learning how to manage freelancers and independent contractors well is essential to making the relationship the most fruitful it can be.

As someone who has worked for myself for most of my career and spent more than 15 years as a freelance writer and editorial project manager, I can tell you that some people have great freelancer management skills—and some are just awful. As someone who has hired and managed freelancers, I can say that there are some secrets to making the most of the relationship. My “ride or die” clients share these attributes and, in exchange, have independent workers who care about them and are committed to their success.


Most of my long-term clients are good at vetting the people who work for them. They get referrals from people they trust and work to build teams of trusted freelancers to whom they turn again and again rather than hiring and training new talent all the time. They want people who are skilled and reliable and who don’t need a lot of hand-holding.

For freelancers, finding a good “anchor client”—a customer who delivers repeat business over time, alleviating some of the hustle that goes along with working for oneself—is motivation for delivering excellent work and added value.


Talent management isn’t just for full-timers. Of course, your independent workers are just that—working on their own. But you can still get to know them and what motivates them. What are their goals? What types of work do they like to do and do best? One of the advantages of using independent contractors is that you can choose exactly the right person for the project you have.

At the same time, working with freelancers on stretch assignments and encouraging them to advance their skills is also a recipe for loyalty. The clients who show an interest in their independent workers as people and work on building strong, long-term relationships are the ones who can rely on their freelancers to help them out when they have an emergency.


Of course, there must be a level of trust—and, often, a nondisclosure agreement—to do so, but if you have the right freelance team members, involve them in brainstorming or strategy sessions. They may bring fresh perspectives. You may even find that your freelancers can handle bigger projects in your organization. Brainstorming and collaboration led to a big website development project with one client and helped me land a fascinating and fulfilling project management gig with another.


Into every life, some rain will fall. Like everyone, freelancers have emergencies and disruptions. Whether it’s an illness, natural disaster, or a death in the family—I’ve lived through all three during my tenure as a freelancer—having clients who are understanding and who will work with you during trying times is valuable beyond measure. I have clients who stuck with me through cancer treatments several years ago, adjusting deadlines and ensuring I had enough work to get me through that terrible time. When they need something, I will do anything I can to accommodate them.

Conversely, I’ve walked away from a few clients who treated the relationship as a commodity, constantly seeking lower rates, demanding impossible turnaround times, or acting unprofessionally. The most productive relationships are based on mutual respect.


Many freelancers work remotely and don’t have insight into the rhythms of the office. When they submit work that needs no revision or comment, the process just keeps moving. If your freelance workers only hear from you when there’s an assignment and when something is wrong, that stream of negative news can wear on their psyche.

Be sure to give positive feedback, too. Periodically, schedule a call for a “state of the union” check-in. You may be surprised to find out that your freelancer developed new skills or has new ideas that your team can use. And, most of all, don’t “ghost” your freelancers. Few things make independent workers feel more undervalued than unanswered emails, texts, or phone calls. Even if you’re busy, send a courteous response like, “Thanks for checking in. We’ll likely be in touch over the next couple of weeks.”


Most freelancers love what we do, but we work to pay our bills. Fair payment is the hallmark of a good client and shows that the client values the work. When freelancers take out taxes (including self-employment tax), expenses, and lost revenue because of downtime, their hourly rate plummets. And, when an invoice is 75 days late being paid and you’re on your fourth round of the accounting department asking you to send it one more time, good faith goes bad quickly. Chronic late payments will likely wear on the relationship and may even be illegal depending on the terms on your contract and state where the work was commissioned.

Keep in mind that there are some times when cash flow can be particularly challenging for freelancers, especially around the end-of-year holidays and estimated income tax deadlines. Freelancers who operate as sole proprietors or some pass-through entities may have to write big checks to the government on or around January 15, April 15, June 15, and September 15. Be particularly sensitive to paying on time—or even a little early—around those dates.

If you treat them well and manage them properly, your freelance team members can be an invaluable, on-call part of your workforce. As more companies opt for independent talent, learning how to make the most of these relationships will be a valuable skill set in and of itself.

Via FastCompany