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How to Build an Unbeatable Team of Freelancers — and Help Them Reach Their Potential

How to Build an Unbeatable Team of Freelancers — and Help Them Reach Their Potential

Throw a stone in any direction, and there’s a good chance you’ll hit a freelance worker. (But real talk: My lawyer has asked me to tell you not to throw any rocks.)

For the past five years, Upwork and Freelancers Union have commissioned a comprehensive survey of American workers to better understand the state of freelance work in the United States. The most recent report, published in October 2018, revealed that since 2014, 3.7 million additional U.S. workers have taken the leap into the freelancing world — bringing the total up to approximately 57 million Americans. (I’m not playing anymore; put the pebble down.)

They’re spending over 1 billion hours freelancing every week. That’s billion, with a “b.” Sixty-one percent of them aren’t freelancing just to make ends meet but because they find the work creatively fulfilling, and another 42% freelance because it offers the flexibility a traditional 9-to-5 can’t.

Whatever the reason, more people are answering the call to join the gig economy, and the companies that work with them must learn how to build and manage a geographically dispersed team of collaborators and creators. At Influence & Co., we’ve used a pool of freelance writers to craft high-quality content at scale since just about day one, and make no mistake, it’s been one of our best business decisions.

We’ve never aspired to be a content farm, pumping out articles with little thought or care, and we take the same conscientious approach when recruiting, hiring, and working with freelance writers.

For tips on how to write content with care, download The Ultimate Guide To Content Marketing

It’s a Freelancer’s World — We Just Live in It

It’s not difficult to see why modern companies can benefit from working with independent contractors. For one thing, it expands their access to top talent beyond city limits. Some of our own freelancers are local, but others live overseas. Geography plays little to no part in how well we can work with them!

More importantly, hiring freelance writers allows companies to build up an army of micro-specialists. From web development to personal finance to graphic design, you can bet there’s an expert out there.

Under the gig-economy model, you don’t have to hire that expert for a full-time position in order to work with him or her. These are just a few reasons to consider working with freelancers, but if you’d like to know how to build an unbeatable team of them, check out these tips.

1. Recruiting

There’s a reason more companies are relying on referral programs as a major recruitment tool: They forkin’ work. Your employees understand the skills needed to be successful at your company. They also know that, on some level, the referral’s performance will reflect back on them. So they’re more apt to be thoughtful about who they recommend. Referrals, for their part, are less likely to quit and are more likely to be high performers.

Why not apply that same strategy to recruiting independent contractors? If you already work with a handful of trusted freelance writers, ask them whether they know other writers who would be a good fit. Your full-time employees might also know talented writers who would complement your full-time employees’ efforts. Most referrals (41%) are family members or friends, followed by business contacts (32%) and individuals in the referrers’ personal networks (22%).

Don’t forget to share a well-written job description that clearly outlines what success looks like. For instance, our description specifies that we’re looking for writers with specific knowledge in industries such as technology, marketing, and finance. Good candidates must be open to learning new things and have a solid grasp of AP style. Finally, supplement referrals by distributing your job listing on networking platforms such as LinkedIn and freelancer-specific sites such as Upwork.

2. Vetting

When evaluating applicants, it’s key to match your needs to their experience. I’m talking concrete experience that helps fill your skills gaps. Consider what kind of content you need to produce (blogs, whitepapers, guest-contributed articles), who will read the content (business leaders, healthcare executives, Gen Zers), and the subject matter (experiential marketing, capital markets, Lizzo’s flute).


You should also consider the writer’s tonal strengths. For instance, if a candidate’s talents lie in crafting big honkin’ whitepapers for academic institutes, then she might not be the best fit for your short, snappy infographic on the merits of having Pumpkin Spice Lattes available year-round.

Of course, many writers are versatile professionals who pride themselves on being able to write across multiple mediums, topics, audiences, and tones, so don’t confine yourself to hiring only one specific type of human. These are just guidelines to give you a good starting point.

Our vetting process at Influence & Co. also includes a writing exercise. Our writing process is unique, and we’ve found that a test article is a great way to determine whether the candidate and our type of writing are a mutually good fit. We give prospective writers all the materials they’d normally get from our team of editors (a brief description of the article, the goal of the piece, writing tone, target audience, publication guidelines, and an answer set to use as the foundation of the article) and set a deadline for completion. Once the piece is back, we evaluate the work against our quality standards and determine whether the candidate fills an existing need.

3. Setting Expectations

If you decide to onboard a candidate, it’s also important to negotiate the ownership of writing projects upfront via a formal writer agreement. Who will the completed work belong to, and in what capacity can a freelance writer use the work in his or her portfolio? These are important questions you have to be prepared to answer.

Another key consideration is the payment structure. Will you pay by word count, by the hour, or by deliverable? How often will payments be issued? We offer per-article payment, and we issue one payment for all the articles a freelancer completes over the course of a month. However, your answers will depend on the volume of work you need completed, how many freelancers you work with, how your accounting department is structured, and so on.

When you’re ready to assign work to the freelancer, it’s imperative to take a few steps to avoid confusion and frustration. More often than not, you’ll only be communicating with a freelancer via email, Slack, Skype, etc., so you need to clearly outline the scope of the project, provide well-defined writing guidelines, and set a reasonable deadline for its completion.

For instance, at Influence & Co., our writers work within our proprietary system, ICo Core, to complete assignments. We’ve found that it’s much easier to set clear expectations by working within this system because it can house all the project information and support back-and-forth discussion between the writer and editor. We also give our writers 48 hours to complete a standard writing assignment (e.g., an 800-word article for a general business publication). However, we may extend those deadlines based on the scope of the project.

Signed, Sealed, and Delivered

Once you’ve sent out the assignment, you can’t just disappear.


It’s important that you be available for clarifying questions or other concerns. Some of our best work is produced when the editor and writer can have an open discussion around the direction of the content. And once that piece of work is completed? Give the writer some feedback (louder for the people in the back)!

Remember why you started working with freelance writers in the first place: to supplement and complement your full-time employees’ expertise. You need to invest in these individuals in order to continue to help them grow in their craft and, in turn, deliver work that just gets better and better.

There’s no perfect formula for working with freelancers, and we’re still learning — every day — how we can get better. But we’re fully aware of how important independent contractors are to our business. They help us create content: our product! It’s critical that we encourage them and provide them with thorough feedback so the relationship continues to be mutually beneficial.

For a deep dive on how to build a process for content creation that actually works for your company, check out "The Ultimate Guide to Content Marketing" today.

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Picture of Diane McGraw

About Diane McGraw

My life revolves around drinking coffee, reading new books, painting, and working with my editorial teammates, and that’s the way I like it.


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