Want a Successful Relationship with Your Freelancer? Here’s What You Should Know, Pt. I

Between 2010 and 2020, the gig economy grew 15% according to researchers at ADP. There are a number of reasons that the number of freelancers is growing — both freelancers and companies want the freedom and flexibility that comes with working with freelancers.

Here’s my freelance story, in brief: I’ve been freelancing on and off since 2010. I’ve worked with several companies as a freelancer. Some of those relationships have been project-based — when the project came to an end, that was it. Other relationships lasted a number of years.

My freelance experience has given me some insight into what makes a successful freelance relationship. I believe it’s built on two things:

· Finding the right freelancer

· Making it easy for the freelancer to work with you

In this post, I’ll explore what it means to find the right freelancer, and how that helps you create a positive relationship with that person (either in the long-term or short-term).

Why Finding the Right Freelancer Matters

Even if you only plan on working with a freelancer for a single project, it’s crucial that you find the right one. You might think that the most important things about your project are getting it done quickly and under-budget, but that isn’t true.

If you don’t find the right freelancer (and it’s difficult for the freelancer to work with you, although we’ll discuss that in Part II), you waste time, money, and effort. It takes longer to complete the project.

Moreover, the freelancer’s finished work is still a representation of your company and its values, even if they’re not an employee. Regardless of whether the deliverable is internal or external, you don’t want something sloppy or inaccurate to reflect poorly on your organization.

Who Is the Right Freelancer for Your Company?

The biggest factor for finding the right freelancer for your project or for your company will be the freelancer’s experience. Ask yourself these questions when choosing a freelancer:

· How long has your freelancer been doing what they do (writing, graphic design, programming, etc.)?

· Does your freelancer have experience creating the desired work product (blog posts, landing pages, e-Books, etc.)?

· Has the freelancer worked in your industry?

· If the answer to the question above is “no,” is this person familiar with your industry?

· Moreover, is this person familiar with any regulations governing your industry, which could affect your working relationship as well as the project?

· Has this person worked with any industry tools or frameworks that are crucial to the project or company?

· Does this person need a specific set of skills or knowledge (like programming in a certain language or being able to write in Japanese)?

· Does the person have the right certifications or security clearances?

I can bolster these points with two personal anecdotes.

A few years ago, I worked with someone I know who’s a web designer. He knew I was looking for work writing blog posts, so he connected me with a client. This client works in a field with which I have no experience. So, even though I had been writing content for almost a decade at that point, I wasn’t able to write effective content for this person. We terminated the relationship after the first set of assignments.

In retrospect, I should have politely said “no” from the get-go. I take responsibility for my mistake — that’s why I’m sharing it with you now. If you’re looking for a freelancer, make sure they have experience in your industry, or some industry knowledge. Otherwise, you’re going to be unhappy with that person’s work.

A second anecdote involves ensuring that the freelancer uses the right tools. Several years ago, I was a member of a freelancer marketplace (companies post jobs and freelancers bid on them). In these marketplaces, companies can also reach out to freelancers they think might be a good fit for open positions. Someone reached out to me and sounded interested about the prospect of working with me…until the representative from the firm realized I didn’t use a Mac.

If you require that your freelancers use specific tools, be clear about that in any company communications (including job postings and company profiles on any platforms you use, including freelance marketplaces). You don’t want to waste your time looking for freelancers who can’t fit into your workflows.

Other Factors to Consider

Here are some other factors to think about when choosing a freelancer:

· What time zone are they in?

· If you need them to work onsite, will the person be able to do so?

· Will this freelancer be able to meet service level agreements?

· Are there laws in your jurisdiction that might prevent you from working with a given freelancer?

You might find a fabulous candidate, only to discover they’re located too far away to communicate by the end of your business day, or that you can’t legally work with them due to your jurisdiction’s restrictions.

A Word on AI

Is your company using AI? If so, how? What policies have you developed? Are those policies in line with any legal regulations in your jurisdiction?

If you have an AI policy in place, make that clear to the freelancer from the start. That person might be using AI in a way that doesn't align with your policy. When you purchase the freelancer's work, you own it. If that work has infringed copyright law (no one owns AI output), you're on the hook.

Asking for Samples of Work

If you’re going to work with a freelancer, you can ask for a work sample. Be aware that some freelancers are bound by contracts or non-disclosure agreements that prevent them from sharing what they’ve done for other clients with you. In that case, offer them a paid test sample. This gives you the opportunity to evaluate their work, and you get a sense of how they’ll do on the project or at your company.

Conclusion

Finding the right freelancer is half the battle in a successful project or in a relationship. When you find the right freelancer, you know that there won’t be headaches or problems. You’ll get an excellent finished product, and/or you’ll have a long and fruitful relationship.

What qualities do you think the right freelancer possesses? Let me know in the comments.