How Employers Can Ensure Their Freelancers Are Productive

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As we emerge from what’s hopefully the worst of the pandemic, many companies are looking to resume normal working arrangements. Remote work might have helped many of us get through a difficult year, but it’s time to head back to the office.

Except that might not be the case for over a third of the American workforce. That’s how many people worked in the freelance economy amid the pandemic, a 22% increase on 2019 figures. More than half would consider continuing those arrangements in the new normal. 36% are already doing so full-time, and the trend is prevalent among younger demographics.

Smart employers will seek ways to tap this growing pool of freelance talent. You’ll want to establish a policy for working with freelancers, be well-versed in searching top sites’ listings, and make online payments for independent contractors as seamless as possible.

But how do you make sure that your freelancers are really productive, giving you the most bang for your buck?

The vetting process

The rise of freelance work has also seen the industry shed its old reputation for flakiness and poor quality. You’ll find many experienced, hard-working people among the freelance ranks. But the available talent still spans a broad spectrum of skill and professionalism.

Trustworthiness will always be inherent to this industry because getting to know freelancers in person isn’t required. And it’s often more difficult to get the measure of a person through a video call instead of a face-to-face interview. This heightens the emphasis on vetting freelancers to end up working with the right person.

You can let job sites’ algorithms do the grunt work of filtering and matching, but once you’ve narrowed down your search, do background checks. Go beyond reviews and reach out to their previous clients for feedback. And when you’re at the interview stage, ask the right probing questions that will paint an accurate picture of their work ethic, accountability, and relationship management.

Better-defined structure


When hiring a freelancer, many employers default to the simple structure of either billing by the hour or by the project. This is fine if you’ve already established a degree of trust with the freelancer. But it also opens the door for people to drag their feet a little, be less optimal with their productivity, and charge you more relative to the actual work done.

The easy fix is to set up a check-in arrangement. Maybe you agree to have them turn in proof of work in progress daily or weekly so that you know they’re productively occupied. However, this does entail more time and effort for both parties.

How you handle this can be a delicate balancing act because people opt for the freelance lifestyle largely due to the flexibility it offers. You don’t want to micromanage their daily schedule, especially if they juggle multiple clients and projects.

A reasonable alternative is for employers to structure their contracts so that freelancers get paid upon reaching certain milestones related to completion. You may also want to experiment with incentives, offering a lower hourly rate but greater overall compensation if they can meet timeliness qualifications.

Using apps and platforms

Maybe micromanagement appeals to you, or you aren’t comfortable giving workers so much autonomy. Or perhaps your arrangement with the freelancer is explicitly exclusive and presumably compensates them enough for not being allowed to take on other jobs.

The same apps that we’ve been using to collaborate and ensure productivity for remote teams during the pandemic will work here. Time Doctor, Toggl, TopTracker, and the like can be excellent ways to monitor freelancer productivity and hold them accountable. Some freelance platforms, such as Upwork, offer similar functionality.

Once they’ve proven they can meet deadlines, you can loosen the supervision and allow them to operate more autonomously based on trust.

Coaching for time management

Let’s face it, time management itself is a skill, and not many people are good at it. It’s vital for freelancers, but given how many newcomers the industry is welcoming, you can expect to work with someone who meets the job requirements but lacks this skill.

If you’re willing to invest in them, you can use some of your check-in time to better understand how they work. Identify barriers to productivity, such as distractions in the work environment or lack of work-life separation at home. Coach them on how to do better in this aspect, and you’ll be rewarded with a more productive relationship with your freelance talent.

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