Working with Independent Talent: Trust, Accountability, and Preparing for Success

Working with Independent Talent: Trust, Accountability, and Preparing for Success

A growing number of companies work with independent talent on a regular basis: Upwork’s Future Workforce Report found that a majority of hiring managers (59 percent) work with flexible talent, and they anticipate work done by flexible talent will increase by 168 percent in the next 10 years.

And yet, myths still abound about what flexible talent can do, how they work, and whether they can be trusted.

“One of the biggest misconceptions I had was that freelancers were hard to find. The second was that you couldn’t find good quality freelancers online,” said Adam Hoffman, vice president of marketing at Singularity University, during Upwork’s Work Without Limits New York Summit. “[Today] we work with some of the most amazingly talented people around the world to move our projects forward.”

Singularity University, a global learning and innovation community, works with flexible talent in all areas of its business, from marketing to content to business development. Hoffman’s 14-employee marketing team regularly collaborates with 10 independent workers—up to 20 when needed: “It’s important that we have access to freelancers on Upwork so that we can scale and experiment in a more nimble fashion.”

To help other leaders get an inside look at how companies like his get things done, Hoffman hosted a panel during the summit with three of the professionals his team works with:

  • Pep Decker, a digital marketer who specializes in Google advertising
  • Rachel Koeling, a senior content writer and editor
  • Starrena Tapia, a social media and digital marketer

As they’ve built their freelance businesses, each one has run into various misconceptions that people have. Here are some of the FAQs they often field from potential clients.

Q: Can flexible talent be held accountable?

All three professionals agreed that many questions they get revolve around trust and accountability. “Trust comes up in a lot of different aspects,” said Tapia. “Clients wonder: ‘Can I trust that they’ll get the work done in this time frame?’ or ‘Can I trust them with confidential material?’”

Koeling said it even extends to whether she’s capable of working from home. “In fact, I’ve gotten the comment: ‘Oh, so you just sit around at home, pet your cats all day, and don’t do any work.’ But I actually am working.”

Decker advocated that starting small with a paid test project can be key. “Set up an initial project. In my case, a client might say: ‘This is our vision, this is what we’d like to do. Can you help us do a [pay-per-click advertising] audit?’ Or ‘Can you review our marketing campaigns to make sure we have the ship pointed in the right direction?’”

Starting with a clearly defined project works much better than spending money just to see what happens. “Nobody wants to work in such a blind environment, especially when you’re talking about significant amounts of money,” Decker said.

Q: Can I trust an independent professional’s work?

When it comes to trust, Tapia, Decker, and Koeling agreed that many companies don’t consider that trust needs to flow both ways.

“As a freelancer, I can go to multiple companies and be paid by multiple companies. My strong work ethic means I will provide the best work I am capable of to every client that I have,” she said. “At the same time, I also have to trust that my clients aren’t going to look for other freelancers to take over my project.”

Decker observed that public accountability also helps keep everything in check. “When a contract ends on Upwork, you have the ability to leave a public review about how you think I did,” he explained. “If I shafted you for the last three months, you can leave a review that says, ‘Pepp sucks, don’t hire him.’ And then I’ve got to live with that zero-star review on my profile. I have a reputation to uphold and keep going.”

At the same time, Koeling noted, professionals can also leave feedback that forms part of a client’s history on the Upwork platform and it’s visible to other Upwork users.

Q: Can remote professionals take on high-level projects?

“Some people see working with a freelancer as something that’s more short term or a one-off project,” said Tapia. “Or they think working with a freelancer is only for specific types of work, such as tech projects or administrative type work. But it definitely expands beyond that.”

Tapia said there’s an opportunity for businesses to shift their thought process to working with an independent professional as a way to access more resources and specialized expertise—and it’s starting to happen. “Businesses are starting to think, ‘We want to solve a particular business problem, maybe this is an opportunity for us to work with a freelancer,’” she said.

Inside tips to help your talent relationships go more smoothly

Top talent wants to build relationships with their clients: it can help projects go more smoothly, make their businesses more resilient, and be more rewarding over the long term.

“I really look for brands I can partner with, to help them grow over a long period of time,” said Decker. “Singularity University is a prime example of that: We’ve been working together for seven months, it started with enterprise ads and it’s continued to expand from there.”

What can you do to help create those foundations when working with flexible talent? Here’s what the panel had to say about finding (and keeping) top performers.

Protect your reputation
Independent talent can turn to various resources, from Google to social media, to learn more about your company. They may also look for different quality signals on Upwork before submitting a proposal.

“You can see a business’s previous history with freelancers [on Upwork],” Koeling said. “If they have a good background—they’ve clearly worked with the same people over a long period of time—that’s a good sign. You can also go on LinkedIn to check out the background of the hiring manager.”

Do your initial interview via video call
While it may seem like a small detail, a video call can be a much stronger way for both sides to make an impression. “On a video call, you truly get the chance to see the other person and connect with them during that initial interview,” said Decker.

Be prepared to pitch your project
An interview is as much a chance for you to assess a professional as it is for them to learn about you, your company, and your project.

Some of the most important things Decker looks for in a new project include:

  • Do they have a team in place?
  • Do they have a vision he can get behind?
  • Are his values aligned with their values?
  • Are you heading in the same direction?
  • Is this an opportunity for a long-term partnership?

“I want to work with someone who can show me, ‘Hey, we’re trying to build this thing—and just this one thing—and we’d love for you to be an integral part of that.’ That’s really what I’m looking for in these initial conversations. From there, it can lead to discussing scope, timelines, and other details.”

Remember that trust is a two-way street
Ultimately, a strong relationship is built on trust and mutual accountability, whether it’s the confidence that you’re getting an independent professional’s best work or they know you’ll pay them on time.

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Working with Independent Talent: Trust, Accountability, and Preparing for Success
The Upwork Team

Upwork is the world’s work marketplace connecting millions of businesses with independent talent around the globe. We serve everyone from one-person startups to 30% of the Fortune 100 with a powerful trust-driven platform that enables companies and freelancers to work together in new ways that unlock their potential.

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