How Do You Effectively Manage Freelancers?

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How Do You Effectively Manage Freelancers?

The US freelance workforce is currently 53 million strong, and growing fast*. In fact, right now freelancers make up 34% of our national workforce. Sarah Harowitz, executive director of Freelancers Union says, “This is an economic shift on par with the industrial revolution.”


Surprised? Don’t be. The rise of freelance workers is one of four documented workforce trends hitting organizations, and the statistics show that this particular trend is in full swing.

So what exactly is a freelance employee? Freelance workers are individuals who have engaged in supplemental, temporary, or project-or-contract-based work in the past 12 months.

Some managers may groan at the thought of the increasing freelance population. They may think of freelance employees as difficult employees. That’s not true.

Sure, managing freelancers is a little different than managing full-time employees. Yet, a good manager already has the skills to manage freelance employees effectively; she just needs to understand common problems that occur when working with them. Then, she can put helpful protocols in place before things get tricky, and handle situations if they do.

What Kinds of Problems do Managers Face when Working with Freelancers?

Every employee is an individual, freelance or not, which means that possible problems with managing them are a managerial smorgasbord. Trying to address all possible problems is… impossible. Instead, in this series, I will focus on four common challenges managers face when working with freelancers.

Four Common Challenges Managers Face When Working with Freelancers

  1. Inefficient communication between managers and freelance employees
  2. Difficult collaboration between full-time employees and freelance employees
  3. Projects not being completed correctly or on time by freelance employees
    … and the big whopper
  4. Trying to maintain organizational culture and values with freelance employees

Next week, we will dive deeper into how inefficient communication is common between managers and freelance employees. We’ll take a look at the problem, explore a case study, identify a solution, and walk through tips for implementing the solution.

The freelance workforce isn’t going anywhere. It’s one of the four major workplace trends organizations are currently facing, in addition to Baby Boomers retiring (40% of the workforce!), women leaving the workforce in droves, and the switch of the demographic makeup in the majority of the workforce. Managers taking time to work on their freelance management skills will benefit their own experience as a manager, and help the organization as a whole as it faces the future of work.

Are you a freelancer who has experienced a terrible manager, or a wonderful one? What behaviors contributed to both? Are you a manager who has freelance employees? What have you noticed is the most difficult about managing them as opposed to employees you see in the office day-to-day? I’m very interested in your experience. Tell me all about it in the comment section below, send me an email, or find me on Twitter.

*All statistics from the first comprehensive survey on freelancing in eight years — done by the Freelancers Union and Elance-oDesk.


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  1. Josh Futterman
    November 13, 2014

    I would say there is a fifth issue that is at least as important: reliability.

    • Loehr
      November 13, 2014

      Josh, thank you for your input. Reliability is definitely a challenge. I think it goes both ways as well. When a freelancer is working with a client who suddenly vanishes for weeks at a time, it is difficult for them to manage their schedule and income.

      I guess reliability is something to be vetted as much as possible during the hiring process. What do you think?

  2. William J McBurney Jr
    November 13, 2014

    Over a period of more than 30 years, I have managed from 4 to 40 freelancers in many projects ranging from short-term (3 weeks to 3 months) narrow scope to long-term (6 months to 6 years) broad scope, primarily in product and marketing planning and market research, but also in a variety of other fields such as oil product
    import/export brokerage, video applications pilot program field work, and data collection for employment opportunity books.
    The major characteristics of this sort of work are (1) easily set standards of work performance (quality, production levels, deadlines) and (2) time flexibility for the workers (they can put in more time or less time than average and take off any amount of time they want between projects or stages of projects).
    All of the workers I hired and managed were compensated as independent contractors in cash with no deductions.
    I am now an agent for a brokerage firm where I represent sellers and buyers and renters of residential real estate property, in the only occupation with workers licensed by the state while recognized as being both independent contractors and common-law employees at the same time, even though all compensation is in the form of a commission based on the size of each transaction. The agents and non-management associate brokers behave like gypsy freelancers (they may be
    fired at will). The managers spend a lot of time trying to keep the agents motivated to produce more but the projects (sales or purchases or leases) are always done right and on time because that’s the only way an agent gets paid.

    • Loehr
      November 13, 2014

      Hi William. I really appreciate your insight! You make a great point about time flexibility. Many freelancers value that freedom immensely, and don’t want to find themselves in the same rigid schedule they would likely experience in an in-house position. Also, regarding paying in cash– they must have loved that. I believe that paying freelancers fairly and on time makes a huge difference.

      Love the term “gypsy freelancers” for agents and non-management associate brokers! I can see how a commissioned based position as an independent worker would present different challenges entirely. What style of management do you think helps agents succeed?

  3. William J. McBurney, Jr.
    April 18, 2015

    I would characterize the management style as laid-back,
    supportive, congenial but uncompromising on output
    requirements: quick to praise quality and quantity but never
    playing favorites.


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