Working with Freelancers: Building Trust and Success

Working with Freelancers: Building Trust and Success

A growing number of companies work with freelancers on a regular basis—and they’re reaping the benefits.

Upwork’s Future Workforce Report found that 79% of the hiring managers surveyed find working with freelance talent enables greater business innovation. And nearly 80% of the hiring managers working with freelancers say they’re confident they can find the exact talent they need.

Yet some misconceptions and myths about freelance work still exist—questions like:

To help, we’ve compiled some stories, suggestions, and advice from hiring managers and professionals who have found success working with, and as, freelancers.

Can freelancers really produce quality work?

When you’ve relied on an internal team of traditional employees—or one marketing agency—for a long time, outsourcing work to someone new can feel nerve-racking. Some folks only take that step when they have to, because they don’t have the workload or budget to hire a full- or part-time employee internally.

One common reason for hesitation is concern about whether or not a freelancer can produce work that’s up to brand standards. 

Upwork clients will be some of the first to tell you that yes, freelancers absolutely can do this.

Adrienne Young, lead art director at Amway, found herself in a bit of a pinch in early 2020. She needed to create videos featuring multiple Amway Business Owners around the world—but a global pandemic had just made international travel very difficult, if not impossible.

She turned to freelance talent out of necessity—and was pleasantly surprised by their quality work.

“I’ll be honest, I went in with low expectations knowing how complex the project was and how low of a budget we had,” Young said. “But when the first video came out, the work spoke for itself.”

The video production team at Microsoft had a similar experience. Ken Circeo, creative director of the Office Video and Production Team, initially thought it impossible to produce the kind of high-quality videos he needed in a short timeframe.

“I was used to producing one video per week to keep it up to the standard I required of any content we produced. Nine videos in 10 days seemed like an impossibility,” Circeo said, referencing a demanding project that pushed him to work with freelancers. “I thought that when I received the videos, I’d have to edit them, so I left time for that. I didn’t have to touch them. The work was fantastic.”

Can freelance talent be held accountable?

If you’ve never worked with a freelancer before, you may be wondering how on earth you can potentially keep them accountable.

An important thing to remember is that when you’re working with a freelancer, you’re working with an independent contractor who’s used to being very self-directed. They may have been self-employed and working as their own boss, or running a small business, for many years. They ensure accountability and responsibility on every project—just as you do for your customers. 

As a client, one of the best things you can do for accountability purposes is to be very clear about what you need and want from the freelancer you’re working with.

“My golden rule, with all my clients, is to make all requirements and expectations crystal clear on day one,” said Asna Tungekar, a data analyst and business intelligence specialist.

Experienced freelancers like Tungekar are often able to help guide new clients through the kickoff process to ensure a smooth start.

“I always make sure to ask relevant questions to ensure I don’t miss out on any important details. Secondly, I make it a point to provide timely status updates,” Tungekar said.

If you’re nervous about starting work with a new freelancer, entering into an initial test project can help. 

Priyanka Sreekanth is an architect and an interior designer who uses the Upwork platform as both a freelancer and a client. She sees test projects as beneficial to everyone involved in a new contract.

“Always start with a test project with your freelancer if you’re apprehensive,” Sreekanth said. “This has worked really well for me, now that I also hire freelancers through Upwork.”

Upwork also offers additional protections for freelancers and clients who are entering into a contract together. 

Whether it’s for a test project or a longer-term engagement, our fixed-price protection, hourly payment protection, and support during any disputes means that all parties get added peace of mind.

Can you trust a freelancer’s work?

Many Upwork clients have found that they can quickly grow to trust—and rely on—freelance talent.

Kemal Yusal, head of business development and operations at Riot Games, turned to freelancers for help while building out an office for Riot’s operations in the Middle East and Africa. They became an integral, trusted part of his operations.

“Our employees trust the freelancers they work with,” said Yusal. “Now we’re more agile and flexible. Our product outcomes are more professional and pristine, and employees are under less pressure.”

The key is taking the time up front to find the right freelancer, with the right skill sets, for your project. Test projects can help with this, too. 

Once that trust is there, you can then begin to fully unlock the potential of working with freelance talent.

Can freelancers take on high-level projects?

Freelancers can definitely take on high-level projects—just ask Vinod Kartha, vice president at UST. He’s seen first hand how freelancers can bring a wealth of knowledge to high-level and complex work.

“Personally, we’ve had zero failures in our use of freelance talent,” Kartha said. “I think it’s not just because we’re getting their general expertise. It’s that they’ve likely solved exactly what we need them to solve a thousand times.”

How can you build strong relationships with freelancers whom you never meet in person?

Talented freelancers—like those you’ll meet on Upwork—want to build strong relationships with their clients.

Samer Bazzi, a freelance marketing professional, explained one reason why.

“I prefer to take on long-term working relationships than short-term projects,” Bazzi said. “While small clients are great, it keeps me on the sales hamster wheel. Every time I finish a project, I have to go get a new client instead of keeping an existing client with continuous income.”

Plus, establishing a long-term freelancer and client relationship helps to make future projects go smoothly—you’ve already built up the bonds of trust, good communication, and a workflow.

Here’s how you can take steps toward building strong relationships on Upwork.

Protect your reputation

Freelancers can turn to various resources—from Google to social media—to learn more about your company.

“I always make sure I believe in the product I’m supporting,” web developer Kevin Campbell said.

Freelancers like Campbell may also look for other quality signals on Upwork before submitting a proposal for jobs, including:

  • How long you’ve been a client on the platform
  • Whether or not your payment method is verified
  • How many jobs you’ve posted
  • The number of freelancers you’ve hired on Upwork
  • How long your contracts with freelancers tend to last
  • The average hourly rate you pay
  • Testimonials from previous freelancers you worked with

Do your initial interview via video call

While it may seem like a small detail, doing a video call during the interview process is worth both your and the freelancer’s time.

“I always start with a video call to introduce myself to my clients and my process,” Sreekanth said. “This way I get a sense of what the client’s expectations are and it makes further communication very easy since I know the client better.”

Be prepared to pitch your freelance project

Interviews aren’t just a chance to assess whether or not a freelancer is the right fit for your project. It’s also a chance for the freelancer to decide if they want to work with your company.

This means it’s important to come to the interview prepared to pitch the benefits of working with your company and on your project—as well as answer any questions the freelancer might have. While these questions will vary, many freelancers are interested to know: 

  • Do you have a team in place already? 
  • Who will they be communicating with regularly? 
  • What’s your company’s vision? 
  • Are there specific values that guide your work? 
  • What kind of partnership are you looking for? 

You can also answer some of these questions up front by creating a detailed job post.

“I look for a clear explanation of the job. Sometimes people put a small description and then want an estimate without an interview. That’s a red flag for me,” Campbell said. “I need to see that the client understands the scope of the work to be done by the amount of details they put on their description.”

8 simple steps for successfully working with freelancers

Taking the leap into working with freelancers doesn’t have to be scary—and it can have immensely positive results for your company.

With Upwork, it’s easy to get started. Just remember to:

  1. Create good job posts with lots of great details about the kind of help you need
  2. Make sure you have details about your company available online
  3. Verify your payment method with Upwork
  4. Take the time to review freelancer profiles and invite your favorites to do a video interview
  5. Be ready to talk openly and honestly about what you need—whether it’s graphic design, copywriting, tax preparation, or something else
  6. Ask the freelancer questions about how they like to work and communicate, as well as their relevant experience
  7. Start with a paid test project if you’re still feeling nervous about jumping right into a big project with a freelancer
  8. Take the leap! You’ll never get to experience all the benefits of working with freelancers unless you decide to give it a try.

You can start right now by creating or logging into your Upwork account and posting your first job or browsing Project Catalog and reaching out to freelancers that interest you.


Projects related to this article:
No items found.

Author Spotlight

Working with Freelancers: Building Trust and Success
Emily Gertenbach
B2B SEO Content Writer & Consultant

Emily Gertenbach is a B2B writer who creates SEO content for humans, not just algorithms. As a former news correspondent, she loves digging into research and breaking down technical topics. She specializes in helping independent marketing professionals and martech SaaS companies connect with their ideal business clients through organic search.

Working with Freelancers: Building Trust and Success
B2B SEO Content Writer & Consultant

Get This Article as a PDF

For easy printing, reading, and sharing.

Download PDF

Latest articles

X Icon