Working with Freelancers on Content Creation? 3 Remote Collaboration Pitfalls to Avoid

By Bethany Johnson on June 26, 2018

Garbage in, garbage out. Most marketing managers already know their people are only as good as the tools they wield. That's why you see so much emphasis on empowering and equipping teams these days. When you give your people the best, they perform. Give them garbage though, and unsurprisingly, they'll produce subpar results.

Transfer this wisdom to remote collaboration with contractors, and you'll see the same outcome. When working with freelancers, especially on content marketing, the quality of what you give will always reflect what you get in return. Simple. The only problem? Most brands assume freelancers arrive on a project with everything they need to crank out engaging content. In other words, no input needed. Many marketing leaders believe there's little (if any) equipping to be done. Why invest in temps the way you would nurture internal content creators?

office workers talking

Image attribution: Charles Deluvio

Glad you asked. By approaching remote collaboration with independent talent as thoughtfully and creatively as possible, you can establish a team of creatives eager to see your brand succeed. Get this right, and you have the potential to ignite passionate, self-fueled brand evangelists. Hit "autopilot," though, and you risk much more than a botched blog post.

Here are some surprising pitfalls companies encounter when treating external content creators like consumables.

Pitfall #1: Entertaining Freelance Pet Peeves

Some of your more risk-averse team members may still harbor concerns about hiring external talent. That hesitation can permeate your department's collaborative efforts more than you'd expect, spoiling more than team spirit and actually affecting your final product.

When working with freelancers, some potential pitfalls are less obvious than others. Here's how to predict and prevent the root cause of three most common snags.

Image attribution: Bernard Hermant

Solution: Address Stubborn Fallacies About the Drawbacks of Hiring Freelance Talent

Bring those fears into the light. Together, tackle each one to determine which (if any) of the risks or hassles of working with remote freelancers truly outweigh the benefits of an agile marketing workforce.

Don't be shy here. Suggest potential catastrophes aloud to determine if these "worst case freelancer scenarios" are more or less detrimental than inaction. Some of these concerns may include:

  • Lack of control. Many managers still prefer to see workers either at their desks or in a green, "online" status. Trusting remote, independent content creators means relinquishing that control in exchange for on-time results. While it's true you cannot force a content creator to sit in his seat until the job is done, you can orchestrate backup plans until you've established trust and built the perfect, well-oiled team of creatives.
  • Excessive back and forth. Internal team members sometimes bemoan the time and energy it takes to bring freelancers up to speed. Again, a little proactivity can solve this easily. Simply keep a living, digital creative guidebook for your internal teammates to edit, and give read-only access to your creatives.
  • Territorial defensiveness. Internal content creators occasionally feel threatened by freelance creatives, a notion that can and should be addressed openly. Reassure your core team that external talent is there to support them and enhance their offerings, not replace them or steal their thunder.

Often, these issues aren't voiced, but instead corrode team-wide relationships. And when that happens, your independent content creators will sense the disconnect. As the outsider, it's never fun working on a brand story when one or two team members don't trust the business benefits of your presence.

Pitfall #2: Failing to Adapt Communications for External Talent

There's no reason to loop in freelancers to every deskside conversation that happens in-office. That's true. However, you can recognize the relational productivity of in-person exchanges and move to offer this same productivity to remote team members. Failing to do so easily results in loss of motivation, creativity, and rapport.

Solution: Communicate Differently with Remote Team Members

First, get clear on the basics. Determine and adhere to technical expectations like:

  • Which remote collaboration software you'll use consistently
  • How your team handles questions that arise after hours
  • Exactly how hungry your internal team is for unsolicited recommendations and how freelancers should submit their suggestions
  • When, how, and why online gatherings take place
  • Where external team members can go to learn more about each employee in the group
  • What resources are available in the event of a misunderstanding or conflict

Next, train your internal team members to recognize the difference between brief communications and clear communications. In today's efficient world, succinctness is often valued over clarity. Really, though, you needn't sacrifice one for the other.

When working with freelancers, some potential pitfalls are less obvious than others. Here's how to predict and prevent the root cause of three most common snags.

Image attribution: Nik MacMillan

Finally, create a space for informal banter, kudos, and birthday celebrations. This move is more than a fun goodwill gift for your people.

"Laughter paves the way for many things," writes Scott Berkun about remote collaboration in The Year Without Pants, his account of his tenure at Automattic. "It's one way to build intimacy between people, something every healthy team needs. Sharing laughter also creates a bank account of positive energy you can withdraw from, or borrow against, when dealing with tough issues at work. It's a relationship cushion."

For example, you might look into creating a fun online forum for swapping cat memes or expressive gifs. It may not sound like much, but it's best if you establish a dedicated place for these (clean) shenanigans instead of letting your remote workers create their own.

So far we've covered remote collaboration as it applies to a presently working relationship. But freelancers are also a wealth of knowledge post departure.

Conduct exit interviews with your favorite freelancers the same way you do when a valued employee is poached by a competitor or decides to head in a different direction. Beyond learning exactly what you could have done to retain that talent, you'll also find out what that outsider believes your team could do differently to succeed. The project-based nature of your past working relationship should not dilute the power of your future potential together, a benefit that could start immediately after parting ways.

From first contact to final payment, communications with your freelance workforce should be valued as the rich sources of information and inspiration they are.

Pitfall #3: Not Investing in Long-Term Freelance Relationships

Many traditional employees still expect yearly merit raises. Hiring managers know better than to anticipate this type of long-term incentive for freelancers, but instead of implementing a replacement perk, companies often passively hope good content creators will simply stick around "just because."

freelance writer working
Image attribution: Hannah Olinger

Solution: Develop, Reward, and Compensate Freelance Talent Competitively

For the last six years, "producing engaging content" has topped the list of B2B content marketers' challenges, according to Content Marketing Institute research. Not budget. Not executive buy-in. What plagues practitioners most is production.

Yet how many of these respondents care for their external content creators as intentionally and resourcefully as they do their internal team? If you treat freelancers as easy-come-easy-go consumables, you'll always have production trouble. Repeat: Don't expect Steven Spielberg-level brand storytelling from a content creator whose name, background, and needs you don't bother to learn.

One of the most popular Content Marketing Institute posts in recent months is a provocative piece called "How to Find a Writer That Won't Kill Your Content." The world is full of self-proclaimed expert writers, yet brands still struggle to find and retain quality contributors. Many times, that's because the best content creators are made, not found. Every marketer who outsources work has had the delightful experience of being pleasantly surprised by a product turned in by a freelancer. When that happens, jump on the opportunity to reward that creative. Why wouldn't you? Compensate potential the minute you see it.

Too often, marketing teams are dismayed to hire a promising freelance trailblazer only to see that unicorn disappear after developing her creative capabilities on your project, proving to you and herself-she's more than a keeper. When one external creative begins to stand out among the others, remember you're not the only one who sees that development. You're competing for the best freelancers the same way you battle for internal talent. Act like it.

Unfortunately, there are thousands of things that can and often do go wrong when hiring and working with remote, independent talent. This is especially true when collaborating with creative people. But if you trace each problem back to its root, you'll find the true pitfall is either culture (allowing your team members to believe less in a freelancer than a permanent hire), communication, or compensation.

To pressure test this theory, run an experiment. Start making the minor changes suggested here, and see what happens to your content production. Feed your creative workforce what they need to produce the kind of brand stories you can showcase.

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Feature image attribution: Andrew Neel


Bethany Johnson

Bethany Johnson is a multiple award-winning content marketing writer and speaker. Her work empowers marketers to ditch interrupt advertising in favor of original content that converts passive readers into active followers. Thriving brands like Tom's of Maine, MasterCard, ADP, Fidelity and the Content Marketing Institute currently rely on Bethany's fresh style to connect with audiences daily. As a consultant, she combines simple change management principles with her insider knowledge of freelancing to show traditional marketing teams how to flourish in today's gig economy. For more, visit