How to Manage Freelancers


Working with freelancers is different than working with direct reports. How do you keep someone motivated when you don’t have formal authority over them? After all, they’re not poised for promotions or bonuses, and the company’s success or failure doesn’t affect them in the same way it affects employees.

Even the most seasoned managers can find it challenging to work effectively with freelancers, but an increasing need for specialized skills and a rapidly growing freelance workforce are making project-based workers a reality for organizations of all sizes.

Here are five tips for optimizing your relationships with freelancers and keeping them motivated to do their best work for your company.

#1: Know the rules.

Relationships between managers and freelancers can quickly go south when a manager doesn’t clearly understand and abide by the legal distinctions between contract workers and employees. Get started on the right foot with a new freelancer by educating yourself. One common misconception is that freelancers can be held to the same schedules and workplace policies as an employee. They can’t. Respecting a freelancer’s independence from the get-go will go a long way toward establishing a positive working relationship.

#2: Set expectations.

Once you understand the rules for working with freelancers, take some time to lay out your expectations for the project, then set up a meeting to discuss them in detail. Put everything in writing. Outline what is expected in terms of output, timelines and quality, and don’t forget to provide context—freelancers don’t have the same insight into the “big picture” that your employees do. If you are looking for something very specific (e.g., a particular style or approach), be clear about it from the beginning. Freelancers are often very good at what they do, but they aren’t mind-readers, and nothing is more frustrating than preventable re-work.

#3: Check in.

An outsourced project can quickly go off the rails when a manager assumes that a freelancer won’t need as much attention as an employee. While it’s true that most freelancers want and expect some degree of autonomy, taking a completely hands-off approach can backfire.

Make yourself as accessible as possible, and ensure that the freelancer knows who to go to for guidance when you’re not available. Setting up a (brief) weekly check-in can be a good way to ensure that questions are answered in a timely manner and that the project stays on track.

#4: Be clear and direct.

The lack of formal authority over a freelancer shouldn’t prevent you from speaking your mind, especially when it comes to job performance. Clear and direct feedback is essential to the freelancer/manager relationship, and should be delivered at every possible opportunity. Remember that positive feedback is just as important as negative feedback—a freelancer may interpret your silence as a sign that something is wrong and inadvertently “fix” something that’s not broken. If you have concerns about a freelancer’s performance, be as specific as possible about what he or she can do to improve. Time is literally money when you’re working with a contractor, and quick performance corrections require concise and honest communication.

#5: Circle back.

Your relationship with a freelancer doesn’t necessarily end with project delivery. Finding, hiring and onboarding new freelancers takes time, so it’s important to invest in ongoing relationships with those you trust. Provide the freelancer with some sort of written assessment of his or her work, even if it’s as simple as “Great job! Can’t think of anything you could have done better.”

Ask for feedback from the freelancer as well, especially if you’re likely to have more work for him or her in the future. Remember that you don’t just choose a freelancer, he or she also chooses you. If you’re difficult to work with, you’ll always be hard-pressed to find the best talent. Be sure to document all lessons learned so that when your next outsourcing opportunity rolls around, you’ll be ready to hit the ground running.