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How to Manage a Freelance Workforce


The freelance workforce has been growing steadily for decades and it’s estimated that The Great Resignation will add 10 million more people to the self-employed. With more people than ever going out on their own, employers are able to access flexible, highly-skilled talent like never before.

This is benefiting them in HUGE ways.

Instead of having to pay for a top-tier expert full-time (or settle for the non-expert that you can actually afford), businesses (especially small businesses) can now hire elite talent for specific projects and tasks. This means you’re getting someone at the top of their game who you don’t have to develop, manage, and hand-hold in order to get the results you need.

Employers can also shop around and “date” freelancers instead of having to “marry” a full-time employee. Need your website designed but want to manage it yourself? Want someone to make you a slide deck but don’t need a full-time graphic designer? Hire a freelancer. You can have them do small, one-off projects and then form longer-term relationships with the ones you really like.

While employers are reaping these rewards, they’re also having to learn what it means to manage a freelance workforce instead of a full-time, in-house staff.

Freelancers go out on their own for a lot of reasons, but many of us do it so we can have more flexibility and autonomy over what we do and how we do it. We’ve made a deliberate decision to take care of ourselves instead of expecting a manager or company to take care of us. That means we actually don’t want you to treat us like employees — if we wanted that, we’d go back and work for someone else.

Now, before I tell you how to treat freelancers like freelancers instead of employees, and why that will benefit both you and them, let’s address the elephant in the room — worker misclassification.

There are big financial, tax, and liability reasons why businesses want to hire freelancers instead of employees. That’s a thorny issue and I’m not giving you professional advice on how to classify your staff, but I will say that I stand in solidarity with workers who are misclassified as freelancers and are demanding the worker protections they deserve. True freelancers choose independent work for themselves vs. the employer making that choice for them.

Freelancers Union said it best, “Worker misclassification is a serious issue, and we stand in support of the hundreds of thousands of app-based workers, delivery and construction workers, and others who are being denied their basic rights by businesses that fraudulently classify them as “freelancers” to avoid having to pay taxes or provide them any benefits or protection against harassment, wage theft, or other unlawful treatment. This deceitful practice creates confusion about freelancing as a legitimate professional choice, also harming genuine freelancers in the process.”

OK, now that we have that out on the table, here’s how you treat freelancers like freelancers so you can build and maintain relationships with the top talent you need.

Treat them like fellow business owners

Employers, you don’t get to have your cake and eat it too. If you want to buy a piece of a CMO, COO, or CFO you don’t get to claim that they’re yours. They built a business model that allows them to do this work for other people so honor that when you represent them externally. In practice, this looks like introducing them as a “fractional” member of your team or a “partner,” mentioning their business name, and letting people know that they’re awesome and work with a variety of clients.

Respect their boundaries

When you have an employee they are at your beck and call for whatever you need (hopefully within reason), that’s not the case with freelancers. A good freelancer should be upfront with you about their response and turnaround time. You are not their only client, so check your expectations when you’re asking them to respond within 5 minutes, join your team’s Slack channel, or have a company email address. 

Don’t let the scope creep

You hire a freelancer for a specific project, they are not here to solve all of your problems or fix your business from the ground up. If you fall in love with a specific freelancer and want them to do all of the things, then have a conversation with them about expanding their scope, what they’re interested in, and their capacity to take more on. This should, of course, come with an adjusted rate. The caveats here are consultants that you have literally hired to analyze and solve your problems or virtual assistants who may have more flexible roles. But even with these types of freelancers, you need to be clear with them upfront about what they’re there to do and let them do it.

Consider them part of the “team”…sort of

Solopreneurship can be lonely. Personally, I like to form long-term relationships with my clients. This gives me the perks of being part of a team (AKA genuine relationships) without all of the top-down control that comes with being an actual employee. In practice, this could look like knowing people’s birthdays and sending them a gift, including them on cool company swag distributions, and just having conversations about real life from time to time.

Don’t try to “develop” them

Part of the beauty of hiring a freelancer/consultant is that you’re getting someone at the top of their game. You’re not hiring for potential, you’re getting someone who knows exactly what they’re doing and can do it at the highest level. I’m not going to speak for all solopreneurs but personally, I hated most of the “professional development” that I had to go through when I worked for other people. Now that I work for myself, I seek out and pay for growth opportunities that feel like a good fit for the direction I want to go with my business and life. When you include your freelancers as “part of the team” this does not extend itself to professional development. If you find yourself needing to “develop” a freelancer, you hired the wrong person.

Treat them like the expert they are

No one likes to be micro-managed, especially top-tier freelancers. You are paying for their expertise, let them guide you through the process and manage their own work. Same as above, if you have to micro-manage a freelancer, you hired the wrong person. 

As the economy shifts to include more independent workers, employers can either embrace this new wave of flexible expertise or get stuck trying to fit freelancers into systems and practices that were built for employees. Freelancing is the future — if you want to leverage it to make your business better, use these practices to get better at managing your freelance workforce.


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