Collaborating with freelancers

Work Culture

How to work better with freelancers


Published on February 09, 2015

Filed under

With freelancers now making up one-third of the US workforce, more and more businesses are tapping into this flexible talent pool. Maybe you need a producer to work on a viral video campaign, but don’t need someone year-round. Or perhaps you’re launching a new company blog, but don’t have the budget to hire a permanent writing staff until you can establish the business case. Going the freelance route lets you bring in extra help when you need it, without necessarily having to hire someone full time. At the same time, managing a freelance team can be challenging, especially if everyone works remotely. At Dropbox, we work with freelancers regularly on a number of different projects, from engineering to design, and we’ve seen many of these challenges firsthand — but we’ve also seen how powerful it can be to have freelancers on board. Here are a few best practices we’ve learned about how to work better with freelancers and be more productive as a distributed team.

Define your goals

Before you start assembling your dream team of freelancers, take a step back to think about your overall business goals. What are you trying to accomplish, and how will the addition of freelancers get you across the finish line? Asking these questions will help you scope out your project, identify the staffing gaps on your team, and plan your budget. After all, the last thing you want is to realize too late that you don’t have enough people (or money) to launch a campaign or finish building your company website. Or, you might bring on several freelancers only to discover that you have one too many people for your project. Either way, it’s important to define your needs up front.

Set clear expectations

So you have a team of freelancers ready to dive in to your project. What next? Communicate your expectations. Kick off your project with a brief that clearly outlines your project goals, what each team member is expected to deliver, and deadlines for each deliverable. Project briefs are a quick way to get everyone on the same page and can help you stay on track throughout the project. If your freelance team is remote, it’s also a good idea to communicate how often you want to check in as a team, as well as your expectations for everyone’s day-to-day availability. Do you want the whole team to dial in to a weekly conference call or would a short email update do the trick? Do you expect team members to be on call during work hours? Come up with some ground rules for how you want the team to keep in touch throughout the day. This way, you can avoid pestering each other with unnecessary chats or phone calls, but nobody is left hanging if something does come up.

Create a shared workspace

Maintaining communication when your entire team consists of remote freelancers can be tough enough. Things can get even harder when you try to work on the same docs or files. Let’s say you’re working with a writer who lives in Seattle and a designer who’s based in Los Angeles. You’ve hired both freelancers to help you create an year-end presentation. Instead of emailing PowerPoint files back and forth — which can quickly get confusing — we’re (unsurprisingly) fans of using a file sync and share solution like Dropbox for Business. Just invite everyone to a shared folder, and they’ll be able to add, edit, or delete files in that folder. So when your writer in Seattle adds copy to the report, your designer in L.A. will be able to see those changes when he opens the file from the shared Dropbox folder on his computer. Nobody has to go through the trouble of cutting and pasting the new copy into a separate file with all the graphics — and nobody needs to book a flight just to make collaboration work.

Build relationships

When every freelancer on your team works in a different city, your working relationships can take a hit and sometimes feel impersonal. Since you miss out on regular, face-to-face interactions, it can be easy to forget that there are actual people on the other end of the line. Make it a point to get to know the freelancers you’re working with — even if they may come and go with the completion of a project. A little bit of small talk can go a long way towards making everyone feel like they’re part of the same team. Want to see some of these tips in action? Check out the story of Valiant Entertainment, whose team works with hundred of freelancers to publish millions of comic books.