How To Upskill Your Team With Freelancers—and Why It’s Worth Considering

The skills employees need are changing fast. The World Economic Forum predicts that nearly 40% of today’s job skills will change or disappear by 2030.

Employees know what’s coming. They see the shift toward skills-based roles in this rapidly changing environment, and they want opportunities to learn.  

But for many small and mid-sized businesses (SMBs), traditional learning and development (L&D) programs are too expensive. And every hour spent in training is an hour of lost productivity. 

Creative SMBs found another solution: Have employees learn while working with freelance professionals.

From competition to collaboration

Not long ago, employees viewed freelancers as a threat to their jobs. But the nature of work has evolved at a rapid pace and doesn’t show signs of slowing, and employees are increasingly embracing freelancers as valuable collaborators.

Upwork research shows that nearly half (49%) of full-time employees rely on skilled freelancers to help them get their work done.

6 ways freelancers can help your team upskill

Freelancers aren’t just filling skill gaps—they’re helping employees level up. Here are some practical strategies that forward-thinking SMBs are already having success with. Bonus: They’re easy to implement.

1. Host hands-on workshops and hackathons

Instead of hiring corporate trainers, bring in specialized freelancers to lead targeted, skill-focused sessions.

For example:

• A freelance social media specialist leads a lunch-and-learn teaching your marketing team how to create more engaging content.
• A data analyst trains teams on learning how to gain insights from data and create clear, actionable dashboards.
• A mobile app developer guides employees through building a simple app in a hands-on session.

2. Learn in the flow of work

Learning doesn’t have to be separate from work. Employees can learn naturally as they collaborate with freelance specialists.

That’s what happened when Emerald Tiger CEO Kim Darling hired Daniel, a freelance industrial designer, to create packaging for her luxury goods product. Daniel delivered more than great design—he became a trusted advisor.

See the full story.

Read transcript

3. Bring in fresh perspectives to fuel creativity

While your full-time workforce has key institutional knowledge,teams can get stuck in routine thinking. Freelancers bring outside expertise and fresh ideas that challenge the status quo.

Jared Steele, CEO of Terrashroom, learned this firsthand. His company was “hemorrhaging money” on a product development agency that couldn’t get his product’s core electrical system to work. Facing the risk of shutting down, he turned to Upwork and found James Elliott, a freelance electrical engineer. Within three days, Elliott built a working prototype—saving the business.

See the full story in this video.

Read transcript

4. Provide on-the-job mentorship

In many SMBs, employees juggle so many responsibilities that there’s little time for mentorship. Freelancers can help bridge the gap while collaborating with employees.

This works especially well when you create a virtual talent bench—a network of trusted freelancers who understand the company’s processes, expectations, and culture.

For example, imagine a junior content creator struggling with engagement. A freelance direct-response copywriter reviews their work, offering feedback that helps them refine their writing, boost conversions, and stay true to the company’s brand voice.

5. Offer one-on-one coaching

Freelance coaches and mentors provide targeted guidance that can help employees sharpen their skills and overcome specific challenges.

For example:

• A team leader struggling with motivation hires a business coach for guidance.
• A CEO experiencing burnout consults an executive coach for strategic direction and inspiration.
• An employee looking to improve their health hires a personal trainer for a customized workout plan.

6. Shadow and reverse shadow workers

Some of the best learning happens by watching others work. Shadowing allows employees to learn by observing freelancers in action, while reverse shadowing lets freelancers study employees and offer new insights

For example:

• Shadowing. A videographer picks up advanced editing skills by watching a freelance video editor handle a project from start to finish.
• Reverse shadowing. A freelance digital marketer sits in with the in-house sales team, offering fresh strategies as they observe how employees engage with prospects via email.

“[Using] freelancers didn’t just save us a lot of time and money, it also allowed us to see our brands through fresh eyes and creative minds. The high-quality work, new ideas, and perspectives are what attract me the most.”
—Kaiyi Chu, former Head of Growth at Lady M

How to choose the right freelancer for your team

Finding the right collaborator takes more than checking their skillsets. Here’s how many companies ensure a good fit.

Define what you need

Here are a few things to consider when getting specific:

• Onsite or remote. Most freelancers work remotely, but if you need in-person training, specify that.
• Skills required. What specific expertise do you want employees to gain?
• Experience level. Do you need a seasoned professional or someone who can explain the fundamentals clearly?
• Mentorship style. Will they provide structured training, real-time collaboration, or coaching?
• Availability. Is this a short-term engagement or an ongoing arrangement?

Check their track record

Some freelancers are great teachers—even if they don’t advertise it. Signs you may want to look for:

• Past work samples. Look for case studies, blog posts, or training materials they’ve created.  
• Testimonials. See if past clients mention the freelancer’s ability to guide teams or offer mentorship.
• Past projects. If you’re using a freelancing platform, such as Upwork, look at ratings and feedback from past projects.

Gauge their teaching skills

During the interview, uncover their communication style, adaptability, and willingness to share knowledge. Here are a few ways to do that:

• Gauge their clarity. Ask them to explain a complex topic in simple terms. Do they sound too technical, get too detailed, or go off-topic?  
• Look for mentoring instincts. Have them describe a time they helped someone grasp a difficult concept. 
• Test their teaching abilities. After they explain a technical concept, ask something like, “I’m having trouble understanding ___, could you explain it differently?”
• Assess their empathy. Are they engaging and approachable? Good mentors are patient and engaging.

Tap freelancer tech

With millions of freelancers available worldwide, finding the right one can feel overwhelming. Upwork streamlines the process, helping you connect with top talent quickly so projects can get off the ground fast.  

Start with the Job Post Generator, powered by Uma, Upwork’s Mindful AI. Just describe what you need in a sentence or two, and Uma will draft a tailored job post in seconds.

Once your job is live, Uma instantly suggests freelancer matches, allowing you to review profiles while additional freelancers apply—so you can find the right fit without the usual legwork.

See: How to hire the right freelancer in 5 steps 

Test the waters

Even with careful planning, surprises happen. A freelancer may be highly qualified but not the right fit for your team, or you might discover that some of your processes need adjusting to better support remote collaboration.  

So reduce your risk by starting small—like a one-hour training session, a single coaching call, or a quick-turnaround assignment. Afterward, evaluate the freelancer’s work and the team’s experience before deciding on the next steps.

Upskill without the overhead

Upskilling is no longer limited to sitting in classrooms or watching one-size-fits-all webinars. With the right freelancers, learning happens naturally as part of the workday.

Freelancer platforms like Upwork make it easy to find skilled professionals who can help your team grow—quickly, cost-effectively, and impactfully.

Start exploring the many ways you can unlock upskilling opportunities for your teams.