Working with freelancers
Small Business & Productivity

How to Work With Freelancers: 9 Tips for Better Project Results

Ever said some version of the following?

“It’s so hard to find good freelancers.”

“Freelancers just don’t feel like part of the team.”

“Freelancers aren’t reliable enough.”

Through my freelance career, I’ve worked with dozens of small businesses. And I’ve learned that the success of freelance gigs comes down to a lot more than how well the contractor knows their stuff. 

Here’s what potential clients should know about how to work with freelancers for a happy, productive relationship and projects you’ll both be proud of.

1. Get Crystal-Clear on the Project Details in Advance—Every Time

A new freelancer/business owner relationship is a bit like dating. You’re getting to know each other, getting third-date excited, and hiding any unsavory habits (at least for the first few months). But as you grow more comfortable with your freelance worker, you may start to let some of your earlier attention to detail slide.

Instead of a clear project brief, you send a slightly vague email. Instead of asking for an estimate, you make assumptions about the cost based on past work. Instead of providing a clear deadline, you trust that the freelancer will somehow glean through osmosis that you need the work for a client presentation in a few days.

Every freelance project should be given the same amount of preliminary care. This is how everyone begins each new piece of work on the same page and leads to happier outcomes for the entire team. Being incredibly clear up front is probably the single most important thing a client can do to work better with their freelancers. Don’t skimp on this part!

2. Provide Context for Each New Project

Freelancers need to know what the deliverable is. But they also need to know where the project fits into the greater business plan. 

Without knowing the full context, it can be difficult for a freelancer to deliver what you want. For example, if someone asks me to write an email to their list, I need to know where that email fits into their overall marketing strategy. What portion of the list is receiving the email? Are they past buyers, or just prospects? Where should the email lead? What other emails has the list been receiving? How successful/unsuccessful have those past emails been?

Without the full scope, you won’t get what you’re looking for, so you’ll be unhappy. The freelancer will have to do the job twice, so they’ll be unhappy.

I just want everyone to be happy.

3. Be Clear About Ownership

Generally, if you create it, you own it. But freelancers do a lot of work-for-hire jobs where ownership actually transfers to the client. So it’s important to be clear about this up front.

When you don’t know exactly who owns the freelancer’s work product, it can set you up for a nasty surprise. 

Here’s a real-life example:

I know a business owner who had a long-standing relationship with a photographer over several years. During this time, the photographer took thousands of photos for the client’s company. Eventually, the relationship soured, and they stopped working together.

About two years later, the client realized that all of the photos that the photographer had taken were no longer in their shared folder. The client reached out to the photographer and asked for his photos back. The photographer told the client in no uncertain terms that they did not have any agreement transferring ownership. So even though the photographer had been hired and paid to take those photos by the client, the photographer still owned them.

And he was right. A jerk, but right.

Make sure that you know who owns the work you’ve commissioned. When I work with clients, my client contract clearly states that all of my work is a work-for-hire. And once the project fee is paid, the ownership transfers to the business. It then belongs to the client in perpetuity. I only retain a non-exclusive license to use the work product in my marketing, like on my portfolio or my Instagram.

4. Don’t be Afraid to Provide Feedback

Do you know what every freelancer wants? Happy, repeat clients. You’re not doing anyone any favors by saying something is fine when it’s not really what you wanted.

Sit with the deliverable for a day or two to gather your thoughts. Try to hone in on exactly what you like and what isn’t what you wanted. Show it to a few people you trust to get their opinion and talk it out to make sure you’re clearly articulating your issues. The more specific you can be, the better. Then, talk to your contractor about it! There may be a very good reason why they approached the work the way they did.

Creative work is collaboration. Freelance service providers are trying to get inside your head so we can yank out your vision and put it on paper. It’s unreasonable to expect that it will be perfect right away, so we generally expect that we’ll need to make some changes.

5. Provide Examples!

Explanations are good, but examples are better. If there is a blogger you really like, send a few of their posts to your content writer so they can emulate that style. If you’ve found a website design that gives off the vibe you want, ask your designer to take a look at it.

Examples may be the most helpful thing you can send to your contractor to ensure you get what you want. Terms like “clean” and “minimalist” may mean different things to different people, but if you can send a sample of what it means to you, it can only help the project. Freelancers will be able to provide better work more efficiently if they have clear examples of what you like.

Expert freelancers can take inspiration from what you’ve provided, but they should never copy someone else’s work. As a content writer and copywriter, I run all of my work through Copyscape’s plagiarism checker to make sure I didn’t even accidentally repeat someone else’s phrasing.

6. Start Out with a Small Freelance Job

If you’re just exploring a relationship with a new contractor, start small! There’s no reason why your first job needs to be a total branding package or full website copywriting.

Send them a smaller project instead. Make sure you like each other and work well together before you go all-in on something massive and expensive.

Hire a copywriter to create an email series before you have them re-write your entire website. Ask a designer to do an event poster before they design your new menu.

Small-scale projects will let you and the freelancer get a feel for each other in a real-work scenario. You’ll be able to see if the freelancer communicates well, meets deadlines, and provides quality work. They’ll be able to see if you respond to questions, have expectations they can meet, and pay invoices on time.

Better to realize that you and the freelancer don’t work well together during a $150 project than a $1,500 project!

freelancer-client contract7. Successful Freelancers Use Official Contracts

If your freelancer doesn’t ask you to sign a contract before you start working together, that may be a bad sign. It could mean that they don’t take their freelance business seriously. Or it could mean that they don’t intend to follow through with their commitments. 

Most likely, it just means they don’t want to pay for a lawyer. 

But as business owners, you both have a responsibility to protect yourselves. A good freelancer should send a formal written contract to each new client to govern the overall working arrangement and prevent misunderstandings or confusion down the line. 

I recommend that freelancers and small business owners who don’t want to pay lawyer fees check out The Contract Shop.* They offer lawyer-prepared legal contracts and templates that you can use to get your legal affairs in order. 

8. On-Time Payments Make You a Better Client

Some freelancers are working a side gig on top of their full-time jobs, which provide a steady salary. But for many of us (like myself), this is a career. Our entire income is earned through our clients. So late payments can have real consequences for our daily lives.

A talented freelancer may have many client options. So if they have a new opportunity come their way, and one of their clients can’t be bothered to pay their invoices on time, then that client just might find themselves without a writer, designer, or photographer next time they need one. 

Prioritize those payments, and you become a much better client!

9. Remember: Freelancers Are Not Employees

Freelance workers are not remote workers, and they’re not employees. The nature of contract work means that freelancers manage their own schedules and choose what tools they use to complete the work. 

This means they may not be available for last minute projects, rush jobs, or after-hours work. And if they do make themselves available to you in these situations, they may charge a rush fee on top of their project fee or hourly rates. 

If you anticipate a lot of short turnaround projects, it may be smart to work with someone on retainer, with the understanding that they’ll provide a certain number of hours or deliverables to you each month, on short notice. 

But this is an arrangement you must make with each freelancer you choose to work with. Freelancers are independent business owners who are often juggling a number of clients and projects. Treat them how you’d like others to treat your business, and you’ll be in good shape! 

Looking for a freelance writer? I know where you can find one. Check out my writing services and let me know how I can help!



This article was originally published on May 31, 2019, and has since been updated.


*I am an affiliate for The Contract Shop, which means I get a small payout if you click that link and make a purchase. I’m also a customer. I purchased my Copywriting Contract and my website’s Privacy Policy/Terms and Conditions from them.

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