Considering contract help? Keep these 10 tips in mind

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A record 4.5 million people quit their jobs in March in the U.S. alone, and the ratio of unemployed people to job openings hit a record low.

While the “great resignation” will eventually run its course, the attitude changes engendered by the COVID-19 pandemic are likely permanent. One of those is the freedom for people to work whenever and for whomever they want.

Upwork reported that 59 million Americans – or 36% of the total workforce – freelanced in 2020, an increase of two million people over 2019.

Bringing on contract help can be an appealing option for resource-strapped businesses, but the vetting and onboarding process for freelancers and full-timers can be quite different.

PeopleCaddie and Upwork are platforms that specialize in marrying contractors with employers in need. I asked PeopleCaddie CTO Tim Rowley and Upwork Vice President of Talent Solutions Margaret Lilani what advice they have for companies wading into the freelance talent pool. Here are 10 tips they offered.

Get everyone on board

It’s unlikely that everyone in your organization will be in favor of hiring contractors, so anticipate some resistance and prepare your case.

“Dig in and say there’s a skill or productivity gap and we need to fill it with the best possible person,” Lilani said. “Set expectations from the get-go.”

Ambiguity or workplace hostility will torpedo your efforts.

Write a clear job description

You’d think “walks on water” is a baseline to read some job postings.

Candidates need to know exactly what is expected of them and how success will be measured—the more specific the description, the better.

Brief co-workers thoroughly

People’s natural reaction to a new face that appears in the office a few hours each week is suspicion. Whose job is getting taken away?

“Address any issues early and set expectations so that everybody knows what is expected of them before a new person joins,” Lilani said.

Screen for specific skills

One of the reasons to hire contractors in the first place is to realize immediate productivity benefits.

“The person needs to be a strong fit, so you don’t have to spend a lot of time training,” Rowley said. “Make sure you screen for the precise skills you want.”

Respect the contractor’s expertise

“These are not just unemployed people looking for a paycheck. In many cases, they are experts in their field,” Lilani said. “Many have long career backgrounds and have chosen to be independent. Think of them as consultants who bring value to your organization.”

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Deliver on the promised workload

If you tell a contractor to expect 10 hours of work a week, you’re on the hook to deliver.

Failure to do so “is a huge hit for the contractor,” Rowley said, and one of the top reasons engagements end prematurely.

Longer engagements are better than short ones

Job security is one of the top causes of anxiety among contractors.

That’s why “the duration of the contract is incredibly important,” Rowley said. “A shorter assignment will be less attractive to strong contractors than a long one. Below about three months interest peters out.”

Make milestones and measurements clear

“If you don’t set expectations that both parties can agree upon from the beginning, then things will break down early,” Lilani said. Success metrics should be quantifiable, clear, and consistent.

Build a bench

Returning to the well every time you need temporary help is exhausting. Contractors value long-term relationships as much as employers do.

“Have a virtual talent bench, so when you get into a pinch, you can go to your trusted team, whether it’s once a week or once a year,” Lilani said. “It’s establishing trust in advance.” Rowley added, “Have 10 candidates in case you need two.”

Make special considerations for remote work

Contractors should use the same platforms you use for tasks like collaboration, videoconferencing, and document-sharing.

When provisioning that technology, pay special attention to access privileges and cybersecurity, particularly if there’s the possibility the person may also work for competitors.

A personal note on using hours as a performance metric: It’s a practice I’ve always hated because it penalizes productive people, but, in many cases, there are no good alternatives.

That doesn’t mean you shouldn’t look for them, though.

A better approach is to pay based on outcomes, whether hitting a milestone, delivering a PowerPoint, or bringing a project in on time and under budget.

Even if you must pay hourly, consider offering bonuses for work that goes above and beyond expectations. Then, everyone will be happier about it.

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