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What I've Learned After Paying More Than $1 Million to Freelancers I've learned three lessons about working with freelancers from a client perspective.

By Erik Bergman

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

One of the many benefits of working in a digital industry like affiliate marketing is the accessibility to talent. Need an experienced web designer to build you a digital application? Want to find a virtual assistant to manage redundant tasks? There are hundreds of qualified candidates at your fingertips.

Through the years, I've worked with many remote workers and have paid over $1 million across all the freelancers I've hired. This investment has given me a unique vantage point into the world of freelancing. In fact, my latest project is a completely remote organization working with digital freelancers in the US, UK and Sweden among other countries.

My first experience with a freelancer was with a writer named Felix. He reached out and offered to write a free newsletter for my previous business. I accepted the offer and after a few assignments, I was a client paying roughly $1,000 monthly for his services.

While access to top talent is easier than ever, there are still rules guiding the client-freelancer relationship — something I have learned time and again. In many ways, how you follow these rules will determine the quality of the work you get in return.

Here are a few key lessons I have learned over the years when hiring freelancers to set them up for success and increase my chances of getting good work back.

Clients need to carve out time for their freelancers

Some business owners contract out freelancers thinking these professionals won't require any additional management, training or resources. They send a vague brief of the assignment and leave the rest up to the freelancer.

I've learned this lesson the hard way as a client, and now understand the importance of investing time on the front-end to set up freelancers for success. It's a lot easier to catch a mistake before the project starts than once you're reviewing the final product. Be willing to put in additional time onboarding your freelancers so you put them in a position to succeed.

If you told five illustrators to draw you a dove and that was the only instruction provided, do you think you'd get identical results? They may all give you a dove, but you can bet their approaches and styles would be unique. If you're not willing to invest time and resources into your freelancers, you can't be mad when they deliver work that doesn't match your expectations.

Managing freelancers is still management. You need to provide clear instructions for your contractors, including outlines, resources and style guides. You also need to be available to answer questions and provide clear feedback at the beginning and throughout the relationship. The more you work with freelancers, the more comfortable you become with the entire management process. Having gone through COVID-19, many business leaders have gained additional confidence in remote management solutions like Asana, Monday, Slack and Google Drive.

If you're willing to put in the time to help get your freelancers up to speed, you'll be much happier with the final results.

Related: No Time for Marketing? Hire a Freelancer.

Freelancers are all created differently

Every employee is different and has unique perspectives, knowledge and experiences. This is especially true for freelancers because they often have a different view of work in general. Many freelancers chose the profession because they wanted to break the 9-5 mentality. As a result, freelancers may sometimes push back on the structure or struggle to integrate into teams and environments that expect traditional work norms.

These differences can present unique management challenges. Are you expecting overseas freelancers in different time zones to work the same hours as your in-house staff? If not, how do you set policies and structure for managing them?

I've found that having an open line of communication with frequent virtual meetings has helped my team create a foundation where freelancers can thrive. While it will definitely take time and you'll need to test different solutions, if you can keep in mind that not all freelancers are created equal — then you're on the right track.

Related: Why the Government's Gig Economy Data Falls Short

Freelancers aren't entry-level employees

While some freelancers are, in fact, entry-level, many have several years of experience working with industries and clients of all shapes and sizes. If you write off your freelancers as low-level workers who complete basic tasks while you focus on strategy, then you are missing out on a world of talent at your fingertips.

If you want to get the most out of your freelancers, treat them like the experts they are. Acknowledge their experience in the field and listen to their ideas. This might require asking them to attend a meeting to share insight on a potential project or giving them the flexibility — once you trust them fully — to make important changes and decisions.

You can also respect your freelancers by paying them what they're worth. With contractors, you get what you pay for. If you are paying writers pennies per word, then you're bound to receive low-quality work. In fact, you may spend more time and money editing or rewriting the article than you would if you just paid for a higher-quality article.

If you operate within a complex industry or have a project with unique requirements, then be willing to pay a premium for a freelancer. If you want to hire someone with a decade of experience, know that their prices will reflect their career success. Underpaying staff and contractors will lead to higher turnover rates, poor work and missed deadlines, leading to unhappy clients.

You can hire a freelancer online to complete your tasks for a few dollars, or you can find a partner, advisor and expert-level worker who can fulfill your needs for years to come. The freelancers you attract will respond to the expectations you set. If you want quality freelancers working for you, then you need to create valuable work experiences for them.

Related: The Business of Freelance: An Increasingly Popular and Very Viable Career Choice

Erik Bergman

Entrepreneur Leadership Network® Contributor

Founder of

Erik Bergman co-founded Catena Media and helped grow it to over 300 employees and a $200 million valuation before stepping away to start, an iGaming organization that donates 100% of its profits to environmental charities.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

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