Regina Olga Mullen

[Written for Replicon blog]

The on-demand economy isn’t just goods and services – these days we want our workers on-demand too. No longer content to pay excess employees during idle periods, we want to hire who we need, when we need them, no matter where they’re located.

Enter the contract worker.

There are many benefits to working with freelancers, but there are potential pitfalls, as well. In this post, we identify three of the most common problems associated with hiring contractors, and offer some tips on how to deal with them.

Problem 1: Poor contractor performance

Performance issues are tricky. The contractor could just be a bad seed, and it may be time to reconsider that contract renewal. But before you pull the plug on a contract, consider that your freelancer’s problems might result from something you could easily remedy.


First, don’t treat your contract employee with kid gloves. Be direct and honest if they’re not meeting your expectations. Workers who think they can get away with anything become complacent, and that can lead to even worse performance. Second, don’t give in to the urge to micromanage a contract worker who’s struggling. Contractors should, by definition, be able to manage their own work. If they can’t handle that, you should start looking for a new contractor.

Next, examine how you’re communicating. Poor communication is a common cause of poor performance, and it’s one of the easiest to address. Be sure you’ve clearly outlined your expectations, and have given the contractor access to the resources they might need – including your time.

If you’re still hiring and are keen to avoid performance issues, look at your contract. Consider using short-duration contracts, especially with new contractors, so you can gauge how they perform without much commitment. Short contracts can also serve to motivate workers with the opportunity for more work at increased rates if they do well.

Finally, managers can consider including pay incentives – offering a bonus for exceptional work can be a strong motivator. This approach is especially useful for fixed-bid jobs, where workers are sometimes tempted to cut corners.

Problem 2: Ineffective communication

When a worker is operating off-site, it’s easy to get your wires tangled. Maybe the freelancer keeps calling you when you only want to keep in touch via email. Or, maybe they’re never available when you want to touch base. Issues like this can lead to frustration and lost productivity.


Make a communication agreement from the start, and be specific. Work out details like how often you’ll meet and when, your expectations regarding their availability, and your preferred channels of communication.

As part of your agreement, you should plan to check in with self-employed workers more frequently than you would with a regular employee – once a week, or more often, if needed. Since freelancers aren’t as familiar with your company’s culture and expectations, they often need more feedback. Still, keep in mind that freelance workers typically have other clients and commitments, so you can’t expect them to be as available as your regular employees.

Since contractors aren’t always broadly available, it’s especially important that you make yourself easy to reach. For example, if you’re frequently out of the office, you could give your contractor your cell number to use if they have an urgent question. If they can’t reach you, you could become the roadblock to their work. And don’t rely wholly on email or other online communication channels. Phone calls and, when possible, in-person meetings are critical to both effective communication and maintaining morale.

With a communication agreement in place, consider getting contractors off on the right foot by giving them an orientation. While this may seem unusual, orientation sessions may be especially useful to contractors since they don’t have the benefit of learning your company’s work style and values by osmosis, as your regular workers do. Plus, workers often perform better when they can see where their works fits into a broader company mission.

Problem 3: Freelancer dissatisfaction

Your contractor’s level of job satisfaction has real consequences on their performance.


Before you do anything else, make sure you’re getting a fundamental key to worker satisfaction right – fair and prompt compensation. Pay the going rate, or more if you really value their work. And if they perform above expectation, consider offering a bonus.

If pay isn’t the issue, you may want to try upping your feedback. And don’t be stingy with praise, either, when it’s warranted. Freelance workers are accustomed to working in a vacuum, and are often desperate for feedback, especially of the positive variety. Telling them how they’re doing, and perhaps more importantly, asking them what would make them happy, are simple ways to improve your employee’s morale.

To further combat the isolation of freelance work, try to integrate them into your organization as much as possible. This could mean inviting them to company parties or sending them your monthly newsletter.

Keeping your sanity

The good news is, managing a freelance employee is a lot like managing a regular staff member. In both cases, you want to make your expectations clear, set up effective channels of communication, provide regular constructive feedback, compensate fairly, and check in regularly to make sure your worker is happy and is meeting goals. But if you do encounter issues you can’t resolve, the real benefit of the freelancer is that they can be much easier to let go.

3 ways to optimize your on-demand workforce