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Management Strategies for the Always-Fluid Workforce of the Future

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Now more than ever, small business workforces are fluid, with owners increasingly turning to freelancers, contractors, and other specialized, on-demand talent who can support projects as needed. A study by LinkedIn found that small businesses are responsible for an estimated 40 percent of all hires across the on-demand economy (for which a projected 9.2 million people will be working by 2021). Additionally, 42 percent of employer firms use contract workers, according to a small business survey by the Federal Reserve.

Fluid work arrangements are becoming more commonplace in the small business community because they offer owners a flexible, low-cost way to scale their workforce. Workers are paid by the project, as managers adjust staffing based on customer demand. A huge number of online platforms, including services like Upwork, Wonolo, and niche sites like Field Nation and UpCounsel, have also made it easier to hire and manage on-demand talent.

But more business flexibility and agility comes with a catch: Fluid workers — most of whom work remotely and intermittently — present new challenges from their nine-to-five counterparts. In this new world of work, a more tailored managerial approach is required.

Here are three tips from real small businesses that have figured it out:


Ask a lot of questions to build rapport.

Tippy Tippens is the founder of Goods That Matter, a New Orleans-based company that sells U.S.-made, eco-friendly goods, and relies on independent creators to make products during busy seasons. Tippens says that hiring contractors over employees brings more freedom to her day, giving her more time to devote to strategic and creative decisions instead of day-to-day staff management.

Tippens’s advice: Build a solid rapport initially so that both sides enjoy the partnership. When discussing project terms, ask a lot of questions to help you get a sense for the contractor’s personality and work style.

In a new project, there are always issues that arise. If you enjoy the person you’re working with, it will allow you to handle the inevitable hiccups more easily. Nourishing strong, mutually beneficial relationships from the start should be every small business owner’s goal, as it will help you to avoid miscommunication, tackle issues collaboratively and maintain a positive partnership.


Be explicit about project expectations.

Martina Brimmer is co-founder of Swift Industries, a bicycle bag company based in Seattle. Her team of contractors support the business with special projects, from sewing bags, to bookkeeping and more. As they navigate the hurdles of growing the business, hiring independent experts allows Brimmer to leverage top talent for areas like photography or design, where they can’t justify a full-time position.

Brimmer’s advice: In the very first conversation, make sure your project expectations and deadlines are clearly laid out.

Most contractors don’t work on-site under the supervision of the small business owner, so it’s important to be completely transparent about project expectations from the beginning. Getting on the same page in terms of deliverables will help you build trust in the freelancer to fulfill his or her commitment, while removing ambiguity on their end and setting them up for success in the project.


Leverage online tools for always-on coordination.

Nexus Academics is an educational consultancy in New York that focuses on college and standardized test preparation. Founder Jacob Feldman relies on a network of freelancers across the region to develop academic materials and coach students. This arrangement is ideal for the heavily seasonal academic industry, as demand peaks in advance of standardized tests and college application deadlines.

Feldman’s advice: Use online tools like Google’s G Suite to stay in lock step with remote workers. Feldman uses Google Calendar to track tutors’ hours, and its integration with QuickBooks Online for easy client invoicing. He also keeps the entire library of course material in Google Docs, and via Google Hangouts, he regularly syncs with tutors to work through materials and conduct meetings.

As Nexus Academics demonstrates, a distributed workforce doesn’t mean that you need to compromise close collaboration and communication. Fortunately, today there is a plethora of online tools available that remove the limitations of physical barriers and help guarantee that all workers feel connected and informed.

It’s an exciting time for small business owners and self-employed individuals alike, as fluid work arrangements are making businesses more nimble and competitive while giving independent workers more control over their schedules. As non-traditional, fluid workforces become even more prevalent, the best practices on how to hire, train, manage, and mentor these workers will continue to evolve.

For now, use this advice as a starting point and remember: Managing independent workers takes a nuanced, delicate hand.

Originally posted to Inc. on October 30, 2017.

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