3 Things To Ask Your Creative Freelancer

Jana Aplin
January 19, 2020

We live during an era with a rapidly growing population of creative freelancers. Whether you’re a thought leader in your industry, a high-level leader in your organization, or an entrepreneur, chances are that you have already worked with or will collaborate with a freelancer at some point. In fact, contracting with a creative freelancer may be one of the best business decisions you can make.

But a creative freelancer doesn’t have an office down the hall or abide by your 8-5 work schedule. They’re often self-employed, and often are trying to capitalize on the flexibility of a freelance schedule as they negotiate life commitments outside of work.

Maybe you don’t have a minute to spare in the office, so you’ve decided to contract a freelancer to help with your overwhelming workload. Or maybe you need a creative person to complement your skills and expand your work. Or maybe you recognize the exponential value of a freelancer who can enhance what you’re already offering to the world. 

How do you—a traditional manager employed by a business—communicate and engage with your creative freelancer?

#1: Ask your creative freelancer for their schedule.

Did you know that some people thrive with daily rhythms, while others work better with weekly patterns, and still others benefit most from monthly routines? Creative freelancers have the benefit of choosing their schedule, but they also need to set one and operate by it in order to succeed.  

Your job may set required work hours, even if you work from home once or twice a week, but you can’t assume your freelancer lives a similar lifestyle. They choose when is the most optimal time for them to work on your projects—which may be eleven on Monday night or ten on Saturday morning.

Ask your freelancer for their work schedule. Don’t hesitate to get specific:

  • What day/hours do you work?
  • When is the best time to reach you via phone, email, or other forms of communication? (Think Slack, Basecamp, coffee meeting, etc.)
  • When should I expect a reply or try to contact you again? (Within 2 business days, by the end of the week, etc.)

#2: Ask your creative freelancer how they track client work.

Now that you have an idea of your freelancer’s schedule, you can discuss how to communicate about your project.

Every worker, from an entry-level assistant to a high-earning CEO, tracks their work differently. Some prefer paper planners with sticky notes or wall calendars that offer a month-at-a-glance view. Digital planners with notifications are a popular option, as are shared online platforms like Monday.com or Asana.

As a self-disciplined independent contractor, your freelancer has to be organized in order to be successful. Find out what method works for your creative freelancer. Ask these kinds of questions:

  • Which days will you spend working on our projects?
  • What platform do you use to track your client work?
  • Is this a shared platform? Will I also have access to this platform?
  • Where can we track our progress and deadlines?
  • How will you share links, images, or research with me?

Why do you care how your freelancer tracks their client work? Because effective communication will enhance your relationship and make your project a greater success. 

For example, your freelancer may give you access to a shared folder in Asana for your project. You can view the freelancer’s assigned tasks and deadline date. Your freelancer can also assign you tasks or tag you to ask for feedback as the project progresses. This keeps all of your communications and information organized and shared in one platform. 

Of course, you can always ask the freelancer to use a system that you already have in place, but by asking them how they work, you may find that you are both using the same platform or, perhaps, discover an easier method of communicating with each other.

#3: Ask your creative freelancer how you can establish expectations and accountability.

We all learn from an early age that reality doesn’t always align with our expectations. A toddler wants a baby brother, until he realizes that the baby takes Mommy’s attention. A teenager can’t wait to own her own car; then reality hits as her pockets empty due to the cost of gas, insurance, and maintenance. 

Adults do this, too, and you should expect some situation to arise with your creative freelancer where expectations don’t match reality. Establish early in your working relationship how to communicate about sticky situations. In fact, don’t hesitate to be bold and lay the groundwork from the start. Consider the following:

  • If you haven’t already talked about the best ways to communicate, now is the time to ask. Email, phone calls, Slack, or another shared platform?
  • Be very clear about your expectations. After a meeting, send a follow-up email detailing the tasks, expectations, and deadlines that you discussed. If your freelancer heard something different from your conversation, you’ll immediately know based on their reply.
  • When expectations are not met, don’t delay talking about it or go radio-silent. Send that email or make that phone call.
  • Ask your freelancer to hold you accountable in return. You’ll check-in when they miss a deadline, and your freelancer should be encouraged to do the same when they are expecting something from you. 

A thriving relationship with your creative freelancer.

Hiring a creative freelancer could be the right decision to make for your project. Their work will complement yours, and you should aim for a complementary relationship too. Ask your creative freelancer about their work schedule, how they track client work, and how to establish expectations and accountability.

There are no wrong questions, but the right questions—like these three—will set you up for a thriving and successful relationship with your creative freelancer.

Editor’s note: Keep reading about how to manage a team of creatives, including freelancers, with this article: 6 Effective Words for Managing Your Creative Team.

Photo by Christin Hume on Unsplash

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