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As Over Half The U.S. Workforce Becomes Freelancers, How Do You Lead Your Top Freelance Talent?

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As experts predict over half the workforce will choose to work for themselves by 2023, your ability to drive change will be the direct result of finding, nurturing and leading freelance talent.

Hiring a freelancer is fundamentally different than hiring a full time employee. Freelancers are predominantly remote. They have multiple clients. And 51% of them wouldn’t work for you full time no matter how much you offered to pay them.

Which creates a new leadership skill - how do you lead remote experts that will never be your employee?

Let’s learn from Stefan Palios, a freelance writer based in Canada who works with clients across North America and Europe.


Stefan’s Path To Freelancing

As an employee, Stefan would most likely be your VP of Content but today is part of the 61% of freelancers who choose to be a full time independent contractor. Stefan graduated from Yale in 2014, started as a full-time research consultant, then worked in startups for a couple years. While writing blogs on LinkedIn, a leader reached out to hire Stefan to write a few blog posts as a freelancer. One client led to two, then as he said, “at one point, I was matching my job income with part-time freelancing.”

After 5 years of working for other people, Stefan chose to become a full-time freelancer in early 2019, a decision that’s quickly becoming the norm as 44% of millennials (23-38 years old) and 50% of Gen-Z (18-22 years old) already freelance. 

Why did Stefan choose freelancing over a traditional career path?

Money and a worst-days analysis. As he said, “I was already able to match my job income with just part-time freelancing, so I knew I could probably make even more money if I focused on freelancing.”

“But then I thought: What would my worst days look like as an employee versus as a freelancer? My worst day as an employee would be working for a demeaning boss who mocked me and my work. Further, it would mean being forced to work at something I had no interest in. On the flip side, the worst day as a freelancer would be handling crappy clients and not being paid what I was worth. I decided I could handle the worst days of being a freelancer better than I could handle the worst days of being an employee, plus it had the potential financial upside. So the decision was easy.” 


Common Leadership Concerns

Why should you trust an independent contractor to have your best interest? 

Stefan currently balances 9 clients. How do you know he has your best interest? 

The answer is quite simple: incentives. Stefan is incented to consistently be on time and on budget with his ideal clients since his livelihood is directly tied to his outcomes and his client’s experience. 

As Stefan said, “I focus all of my work on client outcomes. That’s it. I figure out what my client wants or needs, and then deliver my part of it. On the backend, I set expectations on delivery timelines. I usually overestimate how long it will take me to deliver, which then leaves room to either “wow” my clients by delivering early or having built-in flexibility for “rush” requests.” 

This doesn’t mean he says to yes everyone and everything. Good freelancers are extremely choosy and typically choose a handful of ideal clients.

Why should you invest in someone who will never be an employee?

Stefan is technically an outsider who skipped onboarding. How will he adapt to your company culture and institutional knowledge (all those acronyms)? 

This is a trick question because Stefan might have a working relationship with you longer than some employees. 

Take Stefan’s project helping a venture capital firm revamp their website, brand book, and write a few blogs to kickstart their content marketing. 

According to Stefan, “The project started as a “get it done” kind of project, with backend KPIs around our working relationship plus if the voice / content I produced felt authentic to the partners at the firm.” After completion the working relationship didn’t stop. As he said, “after the initial project, we focused on vision - where the firm wanted to go and the kinds of dealflow it wanted - and that naturally led to more content work. I’ve been working with the client consistently now for over two years”.

Fun fact - the average software engineer tenure is under two years. So Stefan might have more institutional knowledge than your software engineers. 


Setting Yourself Up For Success

1: Make it a partnership, not a transaction 

As Stefan said, “It’s simple: as a freelancer, I work in partnership with my clients. I’m an expert at what I do and they are an expert at what they do. We both have a part to play and that’s great.” 

2: Know what you want (and why) 

Freelancers don’t need onboarding, but they need a clear scope. 

As Stefan said, “the only thing I need from a new client is an understanding that freelancing has to be scoped into a manageable project.”  

Don’t worry, you don’t need to know the exact scope. As he said, “clients can prepare to work with me (or any freelancer) by having an end goal in mind for a project.” 

To best align, include the freelancer in the scoping process. As Stefan said, “I love to work on projects that get me excited and I love to help my clients achieve their goals. Include me in that,  and I can offer my experience and expertise to suggest an approach to take - and that’s how we can decide if we’re a fit to work together.” 

What does this look like in practice? 

In Stefan’s words, his client ICwhatUC is fantastic at knowing what they want. “They share great outlines for blog posts that make it easy for me to understand their core message and audience. From there, I can add style, structure, and tone to actually write the blog itself.” 

3: Pay ASAP and be consistent 

As Stefan said, “I can’t tell you how nice it is to simply know a client will pay you, and not have to expend mental energy chasing them down”.

Remember, it’s a relationship not a transaction. Whether paying on time, including them in scoping, or sharing the big picture, the power of working with a freelancer is establishing a life-long partnership, not just one-time transactions.

It’s an exciting time to be a leader tapping into the Human Cloud. Stay tuned for more about this exciting workforce transformation.

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