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

Photo Credit: Olia Danilevich on Pexels

In my last article, I wrote about one of the steps companies can take when working with freelancers to ensure success. Finding the right freelancer is crucial for projects as well as long-term relationships.

Yet, there’s another component to a successful relationship with a freelancer. This component is based on how easy it is to work with your company.

In this article, I’ll talk about the importance of being easy to work with and the steps you can take to make it simple for freelancers to work with you.

Why Being Easy to Work with Matters When It Comes to Freelancers

You might be wondering why it matters that it’s easy to do business with you as a freelance client. “They should be happy to have my business,” you think.

Look at the situation from another perspective. Let’s say you had a very difficult customer — that individual was very demanding, didn’t communicate clearly, and didn’t pay on time. How long would you want to keep working with that customer?

Moreover, when you don’t do things like communicate clearly or set reasonable deadlines and expectations, you don’t get the finished product you want. Instead, you wind up turning to another freelancer, with the same results, wondering why they just can’t get it right.

When you choose the right freelancer, and you’re easy to work with, you’re far more likely to receive a finished product that meets your specifications the first time around, saving you time and money.

What Does It Mean to Be “Easy to Work With”?

When I think of my freelance clients that are easy to work with, here’s what comes to mind:

· They communicate clearly with me, and it’s easy to reach out to these clients for more information

· They have effective, smooth processes in place, and the right technology to support those processes

· Their expectations are realistic

· Their payment methods are convenient, they pay on time, and they pay me what they owe me

I’ll explain what I mean by each of these points.

Clear Communication

I’ll give you an example of what unclear communication looks like, so you’ll understand why clear communication with freelancers is so valuable.

A company approached me about writing some blog posts. They sent me a summary of the topic. However, they didn’t include the keywords (which is pretty crucial if you’re writing blog posts). They also didn’t tell me whether there were any points they wanted me to emphasize in the blog post. It took another two or three emails to get this information.

Getting the information upfront would have saved me and the company time and effort. This is especially vital when you’re working on a project with a tight deadline.

In addition, you need to make it easy to reach out to you for more information. There might be times when you ask a freelancer to work on an assignment, and there’s something that simply isn’t clear. You don’t want delays to occur because you were the bottleneck in the process. Make it clear from the outset how the freelancer can reach you with questions and how long it will take you to respond.

It’s equally important to provide the right information when the freelancer reaches out to you. Going back to my example above, it wastes everyone’s time when you go back and forth five times because you didn’t provide the right information the first time.

Clear communication is also vital when giving feedback. If you tell a freelancer, “I didn’t like what you did,” that’s not helpful. Point out exactly what you don’t like, and explain what you want so the freelancer has the opportunity to fix the problem.

Photo Credit: Thirdman on Pexels

Effective, Smooth Processes and the Right Technology

We’ll go back to my anecdote above to demonstrate why effective, smooth processes matter when working with a freelancer. The company that approached me was still refining its process for creating content.

Here’s what a smoother process would look like: the company would have sent me a template with everything I needed to know to write those blog posts so that I wouldn’t have to email them several times with crucial questions.

How do you know whether your processes are smooth and effective? Think about how long it takes to get things done at your organization. How many layers of bureaucracy do you have to go through to accomplish a task? Is there always a lot of paperwork, or are processes automated? If things are mostly paper-based, what can be streamlined?

Even if you are using technology-based workflows, are they as efficient as they could be? Are there ways to cut out steps in your processes to make things faster?

Streamlining processes makes it easier for freelancers to work with you, but it also makes you more efficient as a firm.

Realistic Expectations

What do I mean by “realistic expectations”? When you have realistic expectations of a freelancer, you assign that person work that’s within their bandwidth, and you give them a deadline that’s manageable (for example, if you want a 2,000-word eBook, give them at least a week to complete it).

If you have a pressing project, be prepared to pay more for the freelancer to handle it under a tight deadline.

Remember that you are not the freelancer’s only client. They have other clients and other obligations. You can’t expect them to be waiting on you for work, and you definitely can’t expect them to drop everything when you have (what you believe to be) an urgent assignment.

Payment Methods

Back in the fall of 2020, I had the opportunity to work with a major digital marketing firm. I was really excited about being able to work with this firm — the founder is a legend in the digital marketing community. The experience was unfortunately quite negative, in part because of the company’s payment processes.

This company uses a service to send money to its writers, and the service takes a cut of the payment. After a couple of assignments, I was tired of losing a portion of my hard-earned money. I contacted the firm and politely told them I wouldn’t be able to work with them anymore.

One of the ways you can make it easy for a freelancer to work with you is to pay that person in a way that’s convenient and cost-free. In addition, pay the freelancer on time and what you owe that person. If you’ve ever had the displeasure of a client who didn’t pay on time or didn’t pay in full, you know it’s a dreadful situation to be in.


If you’re not easy to work with, you’ll discover that your relationships with freelancers will suffer, and the quality of the finished product won’t be very high. Clear communication, effective processes, realistic expectations, and the right payment processes play a significant role in the success of your project.

What other things do you do to make yourself easy to work with for a positive relationship with freelancers? Let me know in the comments.




Rachel Levy Sarfin is a blogger specializing in B2B technology. She has experience working as a journalist as well as a marketing writer for software firms.

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Rachel Levy Sarfin

Rachel Levy Sarfin

Rachel Levy Sarfin is a blogger specializing in B2B technology. She has experience working as a journalist as well as a marketing writer for software firms.

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