Subscribe to Entrepreneur for $5

This Is How I Manage Freelance Workers and Why It Works

Building long-term but flexible relationships assures you the talent you need, when you need it, at price you can afford.

Opinions expressed by Entrepreneur contributors are their own.

Call it freelance work, contract employees or the gig economy -- whatever the term, it’s consistently growing. In fact, researchers predict that half of the U.S. workforce will dabble in independent work by 2020. The rise of these agile external resources means that today’s leaders need to learn how to better manage off site employees to ensure their organization is equipped to reap full benefits.

Pojcheewin Yaprasert/EyeEm | Getty Images

Related: How to Manage Remote Employees Successfully

As a content strategist, I work with freelancers everyday, typically copywriters, designers and marketing professionals. I’ve found the benefits substantial. My business operates with greater flexibility, I have industry expertise on demand and I keep my monthly burn rate within reason.

However, finding long-term freelance options has proved challenging -- and I’ve found that your business relationships will fail if you don’t lead your contract employees accordingly. Here’s what I’ve learned while growing a business using freelance work and being a freelancer myself.  


Leaders often undervalue freelancers. Contrary to the typical impression, the term "freelancer" is not synonymous with cheap labor, a fungible resource or a second-rate employee desperate for work. While 1099 workers offer more flexibility in terms of employment longevity, they should not necessarily be siloed as temporary solutions. Most freelancers require a grace period of onboarding and education to understand your business mission. If you continue to replace them, you need to reinvest when contracting with others.

The key for leaders using freelancers is to think long term and build relationships that offer repeat working opportunities. This minimizes recruitment costs and helps your team create flexible processes that are designed to scale with less overhead and financial risk of hiring full-time employees. In other words, treat your freelance employees like any other member of your team.

I’ve found that many freelancers, myself included, spend substantial time finding and securing new opportunities to maintain a flexible lifestyle and keep the lights on. Leaders should offer their best contract employees longer term agreements or even consider negotiating a monthly retainer, perhaps at a discounted rate. Longer, fixed-cost contracts also help your financial department determine budgetary needs.  

Related: How to Create a Work Environment That Works Better for the Freelance Spirit

Negotiate flexibility.

Freelancers are a breed of entrepreneurs. They’ve assumed the risk of managing a solo business for the benefits of more freedom and flexibility.

I’ve found that freelance workers are more apt to negotiate a fair working rate, and sometimes it’s not always about the money. This does not mean that leaders should undervalue a freelancer’s work with “exposure” rather than financial gain. It just means that there is more wiggle room when working with a freelancer.

For example, on a recent project for a client, we agreed on co-branding a content program designed for generating new business. Since my business will mutually benefit from the marketing efforts, I agreed to a reduced rate -- and to be honest, I invested more into the project than I typically would because of the added bonus.

Leaders need to be open to alternative methods to maximize their relationships with freelancers. When negotiating with freelancers, research their portfolio, social networks and website for context and start a discovery conversation with small talk. Hold a brainstorming session and discuss possible work scenarios that position both parties interests as a priority. The key is to concentrate more on what you can give the freelancer than what they will give to you.

Remember, don’t assume that they will hop on a reduced rate or alternative payment idea, even if you think it’s a great opportunity.

Related: Don't Believe in Working Remotely? Here Are 2 Strategies That Changed My Mind.

Frontload working expectations.

At the end of the day, when dealing with freelancers, you need to remember that you are running a business, and your time will be limited when managing relationships and negotiating.

Exercise patience with your first few freelance hires to work out any kinks in your business process, develop new onboarding documentation, and ultimately test what works and doesn’t work. But then concentrate on finding a match quickly.

Be crystal clear when communicating your expectations and hire freelance workers for a trial period to determine if their performance and affordability is a good fit for your business. You should have a strong understanding within the first one or two assignments.

While the process of finding, hiring and managing freelance workers can be uncharted territory for today’s leaders, the benefits of flexibility and agile work performance can prove rewarding in today’s economy. To remain competitive, agility is paramount.

Entrepreneur Editors' Picks