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Surely you’ve heard the overly cheesy “if you love something, let it go” parable. This may be sound advice when going through relationship troubles, but it should by no means apply to your decision making with outsourced staff. In fact, the opposite is usually true: if you love the work an outsourced staff member is doing, don’t let them go. Hold on tight, and maybe even consider the possibility of hiring them on full-time. If they’re doing amazing things for you as a contractor, just imagine what they’ll do for you as an official staff member. Even if you aren’t ready to bring on an additional full-time staff member, it’s important to maintain positive relationships with anyone and everyone who works for your organization. It may sound daunting, but it’s easier than you may think.

Check in (a lot)

While it may seem like a no-brainer, a lot of contract workers and freelancers feel alienated because employers don’t check in enough. It doesn’t have to be extravagant; just shoot them an email every week or so, or, better yet, give them a quick phone call. A few minutes of your time can make a world of difference. Holding weekly conference calls or webinars can also be helpful, especially with ensuring that all workers understand your organization’s mission and goals.

Don’t limit your checkups to work, either. Ask contractors how and what they’re doing outside of work, just like you would a full-time staff member. After all, they very well could be one in the near future.

Make yourself available

Most contractors, freelancers and other outsourced staff don’t have the luxury of working out of your physical office space. For that reason, they can’t just walk down the hall and ask a question about a project. And since freelancers often set their own hours, you need to make sure you’re available to answer questions at almost all times of the day. Of course, they don’t expect you to respond to an email sent in the middle of the night, but they’ll be very appreciative of a prompt reply. If you act like your time is too important for them, they will likely reciprocate.

Give feedback and incentives

In basic psychology, positive reinforcement involves the addition of a stimulus after a behavior to encourage the same behavior in the future. If you’ve ever trained a dog—or any household animal, for that matter—you know positive reinforcement like the back of your hand. The dog sits, you give it a treat. The cat uses the litter box, you give it some cat nip. These rewards incentivize the animals to continue those behaviors. Believe it or not, humans work the same way. If your freelancer does incredible work for you, reward them not only monetarily, but with praise and recognition. And, if their work isn’t quite where you want it, help them get there. Provide meaningful, constructive feedback, and, when they get to where they need to be, give them the praise and recognition they deserve. Remember: consistency is key.

Outsourcing work is becoming more and more common, especially for nonprofits. Before you burn any bridges with contractors or freelancers, remember these tips and keep those workers on board for the long-haul.


Jitasa’s tagline is “Numbers For Good” and that’s exactly what they stand for. Jitasa offers Bookkeeping & Accounting Services Exclusively for Nonprofits. They offer solutions that cater to every nonprofit, with simple flat rate pricing that will make your life easier as a nonprofit.