How to seamlessly blend freelancers, contractors, and consultants into your company culture and workflow

a drawing of a face: Skye Gould

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Skye Gould

a person sitting at a table using a laptop: Westend61/Getty Images

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  • Amid the business world’s transition to remote work, tapping flexible workers — such as contractors, freelancers, and consultants — can be more valuable than ever.
  • But managing the legal, logistical, and cultural implications of such hires can be a challenge with a blended and diffuse workforce.
  • Business Insider spoke with several experts for their advice about how to seamlessly integrate flex workers into your organization’s talent strategy.
  • Visit Business Insider’s homepage for more stories.

This summer has brought some wildly uneven and unpredictable effects on businesses across the US, resulting in both staggering job losses for some and ramped up sales for others.


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While a lot of attention has been paid to transitioning to a remote workforce, less has been said about how to effectively tap flexible workers like freelancers, consultants, and contractors.

Business Insider curated advice from several experts on how to integrate flex workers into your organization’s talent strategy and came up with three main takeaways.

1. Understand the tax and legal implications of worker classifications

Issues caused by non-compliance with legal and tax regulations can destroy any short-term cost savings of hiring flex talent, said Michael Cole, lead employment counsel at Gusto, an HR and payroll platform for small businesses, “so you really need to think through the classification issues.”

In tax parlance, there are just two classifications to choose from: 1099 contract workers and W-2 staffers. But Cole cautions that state and local labor rules can cause expensive headaches for employers who try to apply their own interpretation of the rules.

The classification has management implications as well.

Most contractors expect a high degree of independence, and a major test of what differentiates a 1099 contractor from a W-2 employee is how much direct control a manager has over how the work is performed. In other words, you could get into hot water for micromanaging a freelancer.

2. Consider hiring someone to incorporate flex talent into your long-term strategy

Will Lopez, head of Gusto’s accountant community and founder of accounting firm AdvisorFi, stressed the importance of people-focused, transparent leadership when designing and executing a staffing change, especially during a crisis.

Hiring a “flexible talent resource manager” can help. The job falls somewhere between HR and procurement, borrowing a little from each: finding the right people that can boost your team and negotiating and managing contracts with talent sources.

Like remote work, flexible talent is much more than an emergency measure to get through a tough time, says Stephanie Nadi Olson, founder and CEO of We Are Rosie, a company that contracts marketing experts out to national brands like IBM and Bumble.

“Reconsidering your long-term labor strategy to incorporate more flexible talent is going to be critical moving forward because it solves agility challenges, it solves efficiency challenges, and it also solves diversity,” she said.

While highly specialized contract companies like We Are Rosie provide clients with an account manager to scope out projects and scale support according to specific needs, Olson recommends that organizations assign someone to coordinate the different contract labor relationships a company has.

3. Commit to train, delegate to, and trust your new talent

If your team needs to take on flexible talent, it’s important to actually trust those new workers to get a job done. When hiring experienced contractors, you should feel confident they can complete an assignment with little training.

Once you’ve established the parameters of a project, the contractor should be able to deliver their contribution with relatively little direct management.

“You can’t be served if you’re not delegating,” said Tricia Sciortino, CEO of Belay, a virtual assistant service that provides bookkeepers, website managers, and social media mavens. “You’ve got to be ready to really let some stuff go. Show them how to do something, let them have it, and free yourself up.”

Video: Who’s Hiring: ProLogistix (CBS Los Angeles)

Who’s Hiring: ProLogistix



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