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How To Manage People When You’re Not Technically Their Boss

Freelancers, contractors, and consultants aren’t actually your employees, so managing them takes a different approach.

How To Manage People When You’re Not Technically Their Boss
[Photo: Rawpixel Ltd/iStock]

“This looks terrible,” I heard my manager exclaim from a few desks away, clearly upset with the graphic designer on the other end of the phone–a freelancer who probably wouldn’t be too keen to work with us again.

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The more companies tap the freelance economy to handle major tasks and projects, the more managers have to collaborate with people other than their direct reports. It can be tricky to know the right thing to say when you’re managing a project that’s being done by people other than full-time employees who you see every day.

During my career I’ve helped hire and onboard hundreds of freelancers and outside contractors, and I’ve worked personally with many of them. While I’m still learning, my experience has given me a crash-course in third-party project management. Here are a few tips for making it work.

Be Nice–And Don’t Dictate

  1. “This logo design is bad, please try again.”
  2. “Thank you for your hard work on this. I love the colors you used, but I’m wondering if we could work a bit more on the positioning of the font on this logo.”

In my experience, feedback option #2 will outperform #1 any day of the week. While being nice should be common sense, I’ve heard countless contractors receive soul-crushing feedback about their work; in fact, I’ve gotten it myself. Just because you don’t have a longstanding relationship with a contractor you’ve hired to tackle a certain project doesn’t give you license to boss them around. Not only is it unprofessional, it’s counterproductive.


Related: We Need A Massive Remote-Worker Hiring Spree In The American Heartland


Cary Collier and Doug Chambers, the cofounders of a spa and wellness consultancy called BluSpa, collaborate with freelancers daily. They take the trouble to define a clear work scope and offer examples of deliverables, so as to keep expectations on the same page.

“We do not tell contractors exactly how to do their work–they do not want to hear this,” Collier and Chambers explained to me by email. “We quarterback or orchestrate the process, review work along the way, and strive for joy in the collaboration versus pain.” In other words, they approach their freelancers like a creative braintrust, not a stable of workhorses.

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“We ask our team’s opinions instead of telling them how to do something. This method is simple and productive and helps our creative consultants feel a part of our team and the decision-making,” they explain. Just dictating instructions is no way to lay the groundwork for long-term collaboration.

Pay On Time

When my business was first getting started, I was living from client check to client check. I always appreciated those who paid for their completed project in a timely manner. So now, when I work with contractors, I try to pay their invoices as soon as possible.

From the freelancer’s perspective, a late check is more than just a sign of slow cash-flow. It can make you question your own ability. “Maybe they hated the work” or “maybe they’re mad that I’m billing them” are among the crazy thoughts that have gone through my own mind while I’ve waited on a pending invoice. Paying your invoices on time will keep your contractors happy and more likely to want to work with you again. More than that, it shows you value the partnership, which leads to a more transparent, productive working relationship. In other words, as simple as it sounds, paying on time is a crucial management strategy.


Related: Why Freelancers Need A Nonpayment Law


Yes, sometimes your accounts-payable department is backed up and you need to pay late. But if that’s the case, every good manager of freelancers and contractors needs to communicate the issue and give as solid a time estimate of the delay as possible. Whatever you do, don’t avoid that uncomfortable conversation.

“Apart from the financial aspect, prompt payment shows respect for your time and the work that you did.” Suvdeep Bagui, the founder of marketing agency Storepush, adds. “Paying on time and communicating builds trust, which is essential for a stable and pleasant work arrangement.”

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Invest In Your Freelancers

Freelancers can seem like an inexpensive alternative to hiring a full-time employee. You might think that the whole point of doing so is that you get high-skilled expertise for the one project where you really need it. But that still doesn’t let you off the hook as a manager from bringing your contractor up to speed properly. At a bare minimum, some measure of training is critical to making sure any collaborator understands your company and its goals. Too many in-house managers don’t make even that basic time investment–and then end up paying the price themselves.

“In my experience, the lower the rate someone charges, the more time I have to spend on instruction, editing, and feedback,” says Andy Boyer, founder of a multimedia content agency Scribes and Storycasters. “If I’m working under a tight deadline, the extra few dollars I spend is well worth the value of my time,” he explains.

“When you hire a new freelancer, remember they are bringing with them a style bias toward all their previous work, not yours. Share your branding guidelines and messaging frameworks with them early,” Boyer says, “or you’ll be editing their work for tone later.”

When Someone Isn’t The Right Fit, Don’t Pretend It’s All Their Fault

When I was looking for graphic designers to help me create my retail products, I evaluated more than 300 contractors. While some had amazing styles, their design aesthetics weren’t always what I was looking for. Sometimes it takes a bit of trial and error to find the right team. So whenever I’m about to hire for a big project, I often like to contract for a small project first, just to make sure the freelancer and I have the same vision and working style. This is a good management strategy whenever you’re considering giving anyone on your team an unfamiliar assignment–just start small.

It also forces you to plan properly as the person who’ll be managing that work. When I’m getting ready to hire for a new design project, I try to plan exactly what I’m looking for before sharing my vision with a third party. In my case, that means finding examples of styles I like, choosing color schemes, and even mocking up samples on my own. Yes, that can create some up-front effort, but it leads to a more productive collaboration later down the line.

“Before you hire a freelancer, be crystal clear on your needs,” advises Jon Youshaei of the comics site Every Vowel. “I always ask myself: Do I have a vision of what I want? If I don’t, I can’t effectively communicate it when giving feedback to a freelancer, and it’ll just end up wasting time and money.”

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Working with freelancers can be wildly rewarding and can give managers a fresh perspective from outside the company. But if you don’t preserve these relationships, it can be a pretty disjointed, mercenary experience for everyone involved. “Too many freelancers do work and have no idea what happens to it,” Youshaei points out. “I let them know how much I appreciate their work and how none of this would be possible without them.”

This way, when one contractor turns out not to be a good fit for a certain project, the working relationship is intact for a future one.

About the author

Arianna O'Dell is the founder of Airlink Marketing, a digital agency that helps hotels, restaurants, and travel destinations attract and retain clientele. When she's not working with clients or traveling, you'll find her making fun gifts at Ideas By Arianna.

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