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Gig Workers

'Don't Try to Herd Cats' -- and 4 Other Leadership Tips for the Gig Economy

Considering that 1 in 3 workers today are freelancers, you're probably managing one or more of them now or will be soon.
'Don't Try to Herd Cats' -- and 4 Other Leadership Tips for the Gig Economy
Image credit: Marser | Getty Images
Guest Writer
President and CEO, The NHP Foundation
8 min read
Opinions expressed by Entrepreneur contributors are their own.

At first glance, I may not seem like an expert on leadership in the gig economy. Certainly I’ve led traditional work teams, as a partner in several private equity real estate investment firms, and for the last nine years I've been the president and CEO of a not-for-profit developer of affordable housing.

Related: This Is How I Manage Freelance Workers and Why It Works

But don’t be misled by my seemingly staid, parochial business background: We’re all in the gig economy now and there are some smart rules to abide by if we want to succeed. 

You may still think of the gig economy as all freelance writers and Uber drivers, but it’s so much more. According to the Bureau of Labor Statistics, the “contingent” workforce comprises 16.5 million people, and nimble businesses everywhere are turning to this type of talent. The reasons vary. According to a recent survey from Monster, recruiters say “It’s harder than ever to attract high-quality job candidates.”

Connecting with contingent workers often fills this void, but managing this workforce is something else: Nurturing successful partnerships that produce quality business results takes some simple but often overlooked concepts.

Our business employs contingent talent in capacities ranging from graphic design to tech to asset management, to onsite resident services management at our properties. So I've learned a few things. Drawing on conversations with other leaders as well as freelancers, I can offer the following lessons I've learned about managing in the gig economy.

Don’t try to herd cats.

Successful independent workers operate best when free of traditional work rules. This doesn’t exclude deadlines and “codes of conduct” but it does imply that management should accept unconventional work hours, personal styles and even modes of communication.

As one of those managers, you will be a much happier leader of these team members if you stop sweating the small stuff. Instead, concentrate on the quality of the work product and attention to detail. If that is up to snuff, the partnership will be successful. According to independent construction project manager Andrea Syracuse, the worst sin that well-meaning employers commit is failing to develop mutual trust, especially if work styles differ somewhat. “If you micro-manage the first project we do, that is understandable, but loosen the reins on the next and we will both be really satisfied with the outcome," Syracuse told me.

Related: 4 Ways to Successfully Blend Gig Workers Into Your Team

Set realistic, as well as “reach” goals. We have found that our freelancers work best with well-defined goals and timetables. We discuss what is realistic as well as aspirational, 

Keep in mind that these talented individuals have chosen to work for several companies, rather than just one. Recently, our team was tasked with finishing three annual reports in a tight time frame. We set the bar high but offered plenty of support. Working together and conquering challenges as they arose, we accomplished the task in record time.

Freelance graphic designer Rita Lascaro told us: “It’s invaluable to create a shared document with tasks listed, so the independent worker can update the status of many projects, checking off completed ones. Then, instead of multiple emails, the employer can quickly check on what the independent worker is up to.”

Go deep on niche.

One of the wonderful truths about hiring a gig economy worker is the number of people specializing in niche work. These aren't people you’re going to need every day for every project. However, when a team needs someone to excel at a very specific task, an indy specialist can be your go-to.

Joshua Holtzman is the CEO and co-founder at InterviewJet, a members-only hiring platform for tech companies. For quick, small jobs, he told us, he likes some of the “specialized online gig platforms that enable rapid-fire hiring of a particular type of talent, varying from MBA graduates to support research projects to more mundane jobs like picking up office supplies."

Of particular help to Holtzman? Amazon Mechanical Turk, he says, is “a crowdsourcing marketplace that makes it easier for individuals and businesses to outsource their processes and jobs to a distributed workforce who can perform these tasks virtually.” Holtzman has been very pleased using the service for administrative tasks. “I sent a list of 100 data-enrichment tasks that needed to be done and multiple 'turks' (people) followed the instructions and did a handful of the tasks each," he told us.

"Breaking it up into micro tasks made it go quicker than one person could have possibly done it. Like with most gig assignments, the key is spending time to make the instructions very clear.”

Particularly for technical skills in rapidly changing fields, like web design, and for creative skills that require a long time to master, like video animation, Tim Parsons, at 5:00 Films & Media, advises that it’s often a better investment to borrow those skills from “gigsters” on an as-needed basis.

“It’s like being an orchestra conductor,” said Parsons of hiring freelancers for video production. “We don’t have the time to learn how to play every instrument; our job is to know when to call on which specialists in what order to create a unified whole."

Create a culture that motivates … and respects.

It's true that gig workers are entrepreneurial by nature and cherish independence, but they also want to share in the team spirit that guides any company to success.

Lead your contingent workers the way you lead full-time staff.  Share common goals and trumpet accomplishments with the entire team, regardless of their official employee status. Include your gig workers in staff meetings, social events and other appropriate gatherings.

“It comes down to valuing all team members,”  Bruce Starr, partner at BMF Media, told us. “We're constantly seeking specialists who can be flexible to work on an influx of large-scale experiential assignments around the world," he said. "We've had great success by always providing clear expectations of the role on both sides and treating these ‘free agents’ with all the respect we accord our traditional workforce. We find respect to be a tremendous motivator.”

From a freelancer's perspective, designer Lascaro also tied this notion of "respect" to pay. “We [independent workers] do not receive a weekly paycheck and would like to be paid in seven to 14 days instead of 30 to 90," she said. "Those clients who pay immediately, upon completion of a job, rise to the top of my ‘want-to-work-with’ list.”

Leverage shared connections.

Networking is one of the great bonuses of dipping into the pool of “indy workers.” Once your company is on the radar of this talent sector, other qualified contractors will want to work with you. So, take advantage of your workers’ links and bring people in to chat, even if you’re not ready to commit.

Independent contractor Syracuse said: “Some of my best jobs came about after a client and I developed a good rapport discussing industry trends and swapping advice.” Keep in touch with these shared connections so that when the need arises, you’ve got some good candidates in the wings. 

Transition gig workers to full-time when it makes sense.

Much like the stand-out intern who “graduates” to full-time employment at a business, the indy worker who proves his or her mettle, melds into your culture and wants to make the switch, can and should be an ideal fit.

After investing in each other for a good amount of time, this should be a low-risk, high-gain proposition for you both. Bonus: This employee can now help your organization hire – and manage -- your next needed freelancer.

Jeremy Driesen, president and CEO of Ray Bloch Productions, hires freelance help for a few different discrete jobs within his productions.  Based on their performance, and their “fit,” he often offers them full-time jobs. Added BMF Media’s Starr: “While some prefer the flexibility and freedom of being a free agent, the pros -- stability, financial security and desirable benefits -- of a traditional workforce environment just may outweigh the cons."

In the final analysis, Driesen said that when putting together any team, “I don’t necessarily care what they studied in school or what jobs they’ve had. I care about character, work ethic, sense of mission; I need people who can’t get to sleep at night if there are any loose ends.”

Related: Freelancers Make Up 34 Percent of the U.S. Workforce. Here's How to Find, Hire and Manage Them.

And aren’t those the characteristics of any good working team? As you formulate your next freelance hire, remember that, today, according to a study by Betterment, more than one in three workers is a freelancer. Company leaders can either ignore or mismanage these people at their peril -- or embrace them and make them part of a successful business plan.

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