7 Tips for Managing Freelancers and Independent Contractors

7 Tips for Managing Freelancers and Independent Contractors

When people work for you, you want to do right by them. But the rules and expectations are different when you’re managing a freelancer who isn’t fully employed by your company. How do you best motivate someone who you don’t have formal authority over? How do you keep them interested and excited about the work when they don’t get perks like bonuses or benefits? Should you give them performance reviews so they know where they stand?

What the Experts Say
Many managers assume that they don’t need to tend to freelancers as much as they do regular employees—and there’s some truth to that, says Dan Pink, author of Free Agent Nation and Drive. “The relationship is often less fraught, less hierarchical, and doesn’t come with the same expectations,” he explains. But that doesn’t mean that you can be completely hands off. You still need to actively and thoughtfully manage them so that you can get their best output and ensure they’ll want to work with you again. “There’s a growing war for talent for people with specialized skills,” says Steve King, a partner at Emergent Research. Freelancers are often just as valuable as full-time staffers, so employers need to treat them accordingly. Here’s how to successfully navigate your relationship with contractors.

Understand what they want
The first question you need to ask is: Why are they interested in doing this job? “It could be money, the chance to develop new skills, or the opportunity to work with great people,” says Pink. “What are you giving that person in exchange for lending his or her talent to your organization?” Because you won’t know freelancers as well as the people on your team, you may need to put this question to them directly.  (“Just asking is a woefully underused technique in life,” says Pink). You might say, “Tell me what you’re hoping for from this assignment.” Then make sure you’re delivering on that.

Set expectations
At the same time, you need to be clear about what you want in return­—whether it’s a well-designed brochure, a new website, or advice every two weeks. It’s good practice to draft a statement that details exactly what you need and when. It’s also important to provide them with context. Because freelancers aren’t around all the time, “they’re not getting the purpose of the exercise through osmosis the way your employees are,” says Pink. “You have to spend extra time talking about what the goal is, how it connects to the big picture, and why it matters.”

Build the relationship
“It’s fair to say you don’t have to invest as much in a freelancer as you do as an employee,” says King. But, “don’t fall into the trap of making it purely transactional,” warns Pink. Get to know them by asking questions about their family, what they’re interested in outside work, and the other projects they’re working on (assuming you aren’t their only client). This is especially important if you want to work with this person again in the future.

Make them feel part of the team
King’s recent (and not yet published) research on freelancers shows that they prefer to work for employers that treat them like part of the team. So try to avoid all the subtle status differentiators that can make contractors feel like second-class citizens—for example, the color of their ID badges or access to the corporate gym—and be exceedingly inclusive instead. Invite them to important meetings, bring them into water-cooler conversations, and add them to the team email list. Compliance departments in some organizations might worry that doing these things makes freelancers look too much like employees for legal and tax purposes, and managers certainly need to be careful not to overstep any employment laws or HR guidelines. But, King notes: “There’s nothing that says they can’t come to a team lunch.”

Don’t micromanage
Your contractors likely got into freelancing because they wanted autonomy. King and Pink agree that it’s important to give them freedom. “To be a successful freelancer, you need to be self-motivated and able to work without someone looking over your shoulder,” says King. Be flexible with their schedules and other commitments. You’re likely not their only client. And give them space to do their work. “You shouldn’t have to manage the work product of a contractor. If you are, find another one,” he says.

Give feedback
There’s no need to do a formal review with freelancers (“I’m not even a big fan of giving employees performance reviews,” admits Pink) but that doesn’t mean you should skimp on the feedback. Telling them what you think of their work will improve their performance and deepen the relationship. “Besides, most freelancers are starving for that kind of input,” says Pink. It can be as simple as spending five minutes at the end of an engagement discussing what went right and what went wrong but King says continuous feedback is even better. “Regularly revisit the statement of work or contract and be clear about whether they’re hitting their targets,” he advises. “If they’re doing a good job for you, thank them, especially in front of others.” And, if they’re underperforming, don’t beat around the bush. “It’s easy to say shape up or ship out partly because you can boot them at any time and you don’t have to feel as badly about it.”

Pay them well
Don’t think just because the contractor is work-for-hire that you should take advantage. They deserve to be treated fairly. “Pay them market rate,” says Pink, “and if you value their work pay them more.” Even if you’d like to test the person out before committed to a big project with her, avoid asking for work on spec; offer to pay for the time the “tryout” takes.  “People talk to one another,” Pink warns, and you don’t want to risk getting a bad reputation. Your company should “aspire to be an employer of choice—for regular and 1099 employees.”

Principles to Remember


  • Ask what they are looking for from the arrangement
  • Invest time in getting to know them
  • Make them feel like they are part of the team and that their work is valued


  • Neglect to give them feedback on how they’re performing
  • Assume yours is the only project they’re working on—freelancers often have multiple commitments
  • Skimp on paying them what they’re worth—you’ll get a reputation and other contractors may be unwilling to work with you




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