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Turn Your Freelance Workers Into Engaged Collaborators

Sarah Karakaian
Sarah Karakaian

Here's how to get the results you want from your freelance workers.

Younger generations entering the workforce are not beholden to the traditions of the working world. In fact, they've pretty much thrown out the rulebook. They don't want to be defined by their working hours, stuck in a cubicle all day. What they do want is for work and life to be seamlessly integrated, and they want to choose work that's meaningful to them.

We're now seeing the rise of the freelance generation. Compared to the 36 percent of the U.S. workforce as a whole, 47 percent of millennials are making their living freelancing, and over half of all U.S. workers are expected to freelance by 2027.

Facing the fear of freelancers

It all sounds great for the freelancers themselves, but the entrepreneurs and business owners they work with are having a harder time adjusting to this new way of working. In fact, many are experiencing disappointment at the results they're getting from freelancers compared to their in-house employees.

Freelancers often have insufficient direction, especially if they're working remotely and not in-house, which results in misunderstandings about project outcomes. This can be especially confusing if the scope of the project changes partway through. An in-house employee might adapt quickly because he or she can simply walk over to the boss's desk and ask for clarification, but freelancers rely on clear communication to guide their way.

In addition to the demands that freelancing places on communication, it challenges leaders to redefine their organization. Many employers have so far avoided doing this work, and as a consequence, freelancers often feel left out of company culture, which can lead them to being less productive and even disruptive.

How business leaders can inspire the freelance generation

It makes sense that such divergent working styles yield different results. That's why business owners need to alter their leadership style when dealing with freelance and remote workers.

For instance, they should be ready to collaborate rather than control. They should favor flexible and brief meetings for regular communication while increasing collaboration through the use of technology.

If you're an entrepreneur looking to maximize the productivity of these non-traditional employees, consider these four tips to make the transition easier.

1. Pride yourself on clear, direct communication.

Communication (or a lack thereof) is one of the most common ways that freelance relationships go wrong.

The solution is to provide clear, written communication regularly. That way, you'll leave no room for misunderstandings or confusion. Clearly define the hours, pay and project details up front so you can dive into the creative work with no loose ends hanging over you.

Roughly 58 percent of freelancers say they've experienced not getting paid, so by making that information clear at the start of the project, your workers will thank you by working harder knowing they'll be getting a paycheck.

Messaging tools are great for setting up relaxed, regular communication with freelancers, wherever they happen to be working from. And file-storage tools allow for real-time collaboration. These technologies provide a vital way to connect with freelancers, so build a tool stack that makes sense for your unique workers.

2. Include your freelancers in team-building experiences.

Leaders tend to focus on building relationships with their in-house employees because the'’re interacting with them face to face all day, but that often leaves freelancers feeling left out.

This can create a dangerous status imbalance – freelancers might start to feel like second-class citizens, and the imbalance is reinforced when freelancers aren't invited to key meetings, aren't included in message threads and miss out on the casual creative sessions that happen on the fly in the office.

To stop this from happening, make an active effort to get to know your freelancers just as well as you know your in-house team. That could mean sending out regular surveys and get-to-know-you emails or inviting them to pub quizzes and casual hangouts. Whatever it looks like in your company culture, get freelancers into the fold.

3. Give freelancers collaborative control.

All employees want to be collaborators and have a crucial part to play in the daily running and success of the company. Freelancers are no different.

One way to achieve this is to practice a work style known as "job sculpting." This involves empowering employees to make subtle changes to their own roles and responsibilities to boost engagement and motivate them to do their best. For example, allow your freelance designer to make suggestions for how to improve your company website. Or let your freelance editor choose how much she wants to be available via Skype so she can focus on her core tasks.

The reason this handover of control works is because it gives freelancers ownership while increasing the spirit of collaboration, making them feel involved, appreciated and engaged.

4. Pay them what they're worth.

Some freelance relationships sour because the person should never have been hired in the first place. This isn't the freelancer's fault. As a leader, you need to be aware of the personality traits and skill sets needed for someone to succeed in this role.

Hire a freelancer who is over or underqualified, and they won't be able to commit to the tasks at hand fully. They will either get bored and start to look elsewhere or be intimidated into inaction.

The freelance generation presents an incredible opportunity for your company. It empowers you to be flexible, creative and more productive, but it also presents an important challenge to your ability as a leader: to unite diverse talents in the service of a common goal.

Image Credit: Bogoljubb/Shutterstock
Sarah Karakaian
Sarah Karakaian Member
Sarah Karakaian is the host of the popular podcast "Stand Out: Growing Your Organizing and Productivity Business," produced by the National Association of Productivity and Organizing Professionals ( Sarah also has been working with her handy hubby Nick since 2014, creating beautiful spaces full-time at Nestrs LLC — a professional organizing, design, and handyman company. Sarah and her husband are also Airbnb superhosts, and their work and expertise have been featured in the HGTV television series "Beach Flip," The Washington Post,, and The New York Post, among others.