Working with Freelancers: A Two Part Guide

Working with Freelancers - Part 1

If we’ve learned anything over the past few months, it’s that no two work environments are the exact same. While they may share industries and goals, like the often described snowflake, there’s a uniqueness to each born of culture, outlook, and staff. Speaking of staff, one of the things that have been especially notable is the way the traditional workspace has been drastically updated, and that includes freelancers in every possible position.

An evolved workplace

The evolved workplace

In the past couple of years, entirely new industries have sprung up, and along with them, new support staff. While we might toss around expressions, including gig economy and teamlancing, what we’re essentially talking about is a workforce that’s in large part made up of freelancers.

For anyone who hasn’t freelanced or worked with freelancers, it can be a daunting prospect. After all, how can you choose someone who isn’t part of the team to support the team? And once you do hire someone, how can you keep things seamless so your clients have the best possible result without any interruptions or confusion?

The first thing to realize is that the role of a freelancer has evolved. The freelancers I know (including myself!) don’t consider freelancing a casual decision, but rather regard their freelancing as a business. As such, they take their work very seriously, including everything from attracting clients to retaining them and keeping them happy. From the agency side, things look a bit different. Working with a team of freelancers means that an agency could theoretically expand its offerings or branch out into additional markets.

In this two-part article, we’ll be discussing some of the challenges of being a freelancer or working with them, along with advice from those in the know. To begin with, we spoke with two agency heads who work exclusively with freelancers to help understand some key elements involved in successfully working with freelancers.

A virtual PR agency primarily staffed by freelancers:

April Margulies began her career working at top agencies including Weber Shandwick, Edelman, and Rubenstein Public Relations. When she started her own PR agency, Trust Relations, she considered it almost an extension of her successful freelance career. After she landed a big account ($10K/month) Margulies needed help staffing it and turned to other freelancers she knew from previous agency jobs to help.

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tips for working with freelancers

11 tips for working with freelancers

Margulies considers this move to be a smart business model and shared some of her tips for working with freelancers.

Qualifications over availability.

Margulies said that by working intentionally with freelancers, “You could staff each account with the most qualified people for that client, based on their industry experience, etc. (rather than just matching a new client with someone who has the capacity, regardless of the fit, which often happens).”


Margulies considers working with freelance staff to be “a safe way to scale an agency.” You can bring in freelancers when you need them.” And you can also work with them on only the accounts that require their specific qualifications. Margulies said this approach “prevents the mismatched client team that otherwise often happens, as well as the layoffs that are all too common at agencies when the firm loses too many accounts.”

Full-time doesn’t appeal to everyone.

“Many of the most talented publicists I know are no longer interested in working full-time at an agency,” Margulies said. She added that “Freelancers also tend to be happier since they’re setting their own hours and have the freedom to pursue other hobbies and side hustles.” Interestingly enough, Margulies said she knows the freelancers are happier with their current arrangement because she asked almost all of the existing freelancers to join her full-time. She said, “they’re happier with the current arrangement —  even though we offer the standard benefits including health insurance, time off, etc.”

Freelancers invite their networks along.

When starting out, Margulies reached out to freelancers she knew personally. “Eventually, they introduced other freelancers and those freelancers did the same.” When her team needs a specific skillset the team doesn’t have, Margulies turns to word of mouth, LinkedIn job posts, and networking, to find additional team members.

Have someone manage the freelancers.

Last fall, Margulies hired Chief Client Officer Lana Dao, who she credits with implementing processes, including an onboarding process and account management processes. Margulies also has a points system in place, to ensure clients know the agency’s priorities for the month and where their budget is being spent.

Create easily shared templates.

Margulies said her team has templates for everything, including biweekly meeting agendas, recaps, monthly reports, press releases, messaging documents, etc. And,  anyone working with the team in any capacity gets a Trust Relations email and email signature, as well as their bio posted on the company website.

Have meetings only when necessary.

While staff meetings are often the butt of many a corporate joke, they also help a group of freelancers feel more like a team. Margulies believes these meetings ensure there’s also a sense of “camaraderie that leads to a consistent voice.” Be mindful of meeting fatigue though and only schedule as necessary.

Stay connected throughout the project.

For Margulies, that means staying in touch via Slack and Zoom, regardless of location or time zone.

Create perks people will be excited about.

 Margulies and her team send out hand-picked gifts best suited to each team member for their birthdays and work anniversaries. She also has a happy hour every other month and buys everyone lunch remotely by giving them a credit for lunch or paying for their food delivery. She also offers a client referral program in place for anyone who brings in a new client. In addition, she’s been known to give spot bonuses and gifts for great work, including gift cards, silly gifts appropriate to the situation, and even, in one case, an iPad.

Create test projects and pay attention to results.

Before hiring freelancers, you might want to have a trial run, but make sure to compensate them for their time and talents. Margulies brings in new freelancers slowly, so they are on a team with other members the team already knows and trusts. To ensure freelancers integrate into the culture and are a great fit, they begin with limited responsibilities.

Be mindful of finances and your bottom line.

Margulies and her team use something she refers to as T-sheets to plan out how many hours per month can be relegated to every client or project. She then asks freelancers to track their time in T-Sheets on a weekly basis, to see how the actual hours compare with the budgeted hours, to flag any potential issues before they become issues. At the end of every month, freelancers’ tracked hours are converted into an invoice by the HR & finance director, who then sends the timesheets to everyone and has them confirm hours are correct

lessons from.a freelancer collective

Lessons from a freelance collective

Freddie Laker, the co-founder of Chameleon Collective, co-created what he refers to as something of an ecosystem powered by freelancers and careful vetting. He offered some advice on how to attract and retain the top freelancing talent possible.

Hire trusted colleagues. When looking to expand the collective, Laker said he typically seeks out people that one of them has worked with in a prior role. In that way, “someone from within the collective is able to vouch for that person.” But one person’s approval isn’t enough since six separate members of the collective then vet the new hire. Since Laker works in an extremely non-traditional culture, the vetting process is fairly rigid.

Increase diversity. To create a vibrant culture, it’s important to go beyond your traditional networks. Try using your social media networks to amplify your search and encourage others to share your messages.

Decide how interconnected you want your team to be. The Chameleon Collective works with freelancers from all over the world who are teammates operating independent LLCs. “We share resources such as admin, tech, billing, new business, etc but can work as little or as much as we want,” Laker said. And since it’s more like a body of consultants working together for a common goal, Laker said they maintain their independence,  set their own rates, and pick and choose which client projects they want to participate in, and they determine how, where, and when they work.”

Define your collective work style. Laker explained that, at his agency, freelancers are given the ability to work with many of the hallmarks of entrepreneurship. That said, they also all agree to “work collectively in the areas that create value for all.”

Create a feedback program. Working remotely with teams can make it difficult to offer ongoing feedback. Laker said their feedback system is used for both peer feedback and client feedback. “For peer feedback, it’s more about professional improvement for client feedback we use a more traditional net promoter score approach but are always open to direct feedback as well.”

In part two of this guide, we’ll offer ways to manage expectations including setting realistic timelines for each element of the engagement. We’ll also include advice from career freelancers on how to maintain excellent working relationships for the long term.

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About the author

Rachel Weingarten

Rachel is an experienced freelance content creator, content strategist, writer and copywriter, and author of three award-winning nonfiction books. She specializes in business and style and the business of style.