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How managers can give better support to freelancers

As more workers flock to the gig economy, managers must find a way to keep up.

How managers can give better support to freelancers
[Photo: Retha Ferguson/Pexels]

My team at Indeni works with a lot of freelance employees. One day, a previously reliable freelancer just disappeared on us. He stopped communicating, popped in and out of assignments sporadically, and wasn’t giving us everything he had.

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We put our cards on the table during a Zoom call one day. We reaffirmed our expectations and gave him an out in case he wanted to pause or sever the relationship entirely. The situation took a turn for the positive, and he went on to become one of our most tenured freelancers.

Stories like this provide a snapshot of the current evolution taking place in the gig economy. These jobs have transcended the ride-hailing and service sectors to become viable options for knowledge workers and niche industries. And with a 2019 Deloitte study predicting that 42 million people will identify as self-employed this year, gig workers are becoming the norm rather than the exception.

What the growing number of gig workers mean for employers

This shifting standard in the gig economy means workers will require the kind of guidance and support we traditionally associate with full-time employees. At the same time, gig employees enjoy (and demand) a degree of freedom to prioritize their time and effort that companies don’t typically grant full-time staffers.

Managers who want freelance workers to commit time and energy to their pressing projects need to establish credibility and rapport similar to what they’d build with traditional employees. Here are some best practices they can follow to create these mutually beneficial relationships with gig workers.

1. Wash, rinse, and repeat

It might sound counterintuitive to add structure and uniformity to a job that relies on flexibility as a selling point. But repeatability is precisely what makes a continuing gig sustainable. For example, every Uber or Lyft driver knows what they need to do: They pick up customers, transport them, and drop them off at set destinations.

Consistency is key. Indeni’s original process of working with freelancers was loosely structured and focused on writing a few different types of tickets. We soon learned that this confused our freelancers and caused quality to fluctuate, which led us to create a specific process for each type of ticket. These set processes helped stabilize quality and allowed us to spend less energy managing freelancers.

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Of course, this doesn’t mean that you have to micromanage everything. Instead, make sure that each process has a simple, clearly defined, and repeatable structure that contractors can follow. That way, no one should be confused about your expectations.

2. Don’t skimp on resources

Without the right tools to get the job done, even the most capable freelancer will feel lost at sea. Invest whatever time or resources you need to ensure that you’ve implemented the right processes and provided the right tools for the tasks you plan to assign.

My company initially started with tools that worked well for management and not so well for our freelancers. The situation was frustrating enough that some of our gig workers threatened to stop working for us. So we asked them to list the issues they were encountering, including what they wanted that they weren’t getting, and we worked to fix every problem we could. Today, our engineering team works closely with our gig workers to offer the development tools and languages they need to get their jobs done.

It makes little sense to ask a freelancer to do a job but not provide the tools they need to carry it out. Remember, just because they have the skills doesn’t mean they have the correct tools necessary to complete the job.

3. Pay on time

For most gig workers, these jobs are more than just a series of side hustles—they make up a livelihood. Make sure you have a smooth payment mechanism that’s reliable and timely. This can take some effort—especially if you’re hiring people around the world—but it has to be done.

It’s easy to drop the ball when the people you’re working with aren’t company employees. HR and finance departments already have a lot to deal with, so it’s up to managers to act as advocates for their freelancers. Educate your finance department on the importance of timely payments, and help everyone understand the personal impact late payments have on your gig workers.

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4. Keep the lines of communications open

With a distributed workforce of gig workers, it’s likely that management is also spread all over the country (or even the world). This can make communication extremely difficult without established protocols in place. Develop robust management processes for distributed teams by relying on written communication instead of waiting for everybody to be available for a face-to-face meeting or conference call.

Don’t expect email to do all the heavy lifting, though. It’s slow as a communication tool, and its timeline is difficult to follow (easy to fork, hard to merge). Explore a combination of project tracking solutions, such as Jira, and communication tools, such as Slack, to create an effective blend of real-time chat and reliable project management.

As more employees gravitate toward the gig economy, managers have to find ways to keep up. Offering the same consistency, support, and communication to gig workers that you do to full-timers isn’t just a boost to employee morale and productivity. It’s a signal to anyone interested that this new normal of the gig economy is a space where everyone can thrive together.


Yoni Leitersdorf is the founder and CEO of Indeni, which integrates with firewalls and security infrastructures to predict issues and help companies make more proactive business decisions.

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