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Small Business & Productivity

How to Work Better with Freelancers: A Primer

In my current version of life (Life 3.4.2, in case you were curious), I am a freelancer. But in a previous iteration, I had a job that required me to be the primary point of contact for several freelancers. So I’ve been on both sides of this particular tennis court.

Looking back, I can see that there were some things I did that probably drove freelancers nuts. (Sorry, guys.) So to help everyone keep their blood pressure at safe levels, here are a few tips on how to work better with freelancers.

All the Details, All the Time

When you’re starting a new relationship with a freelancer, you want to make sure that you’re going to get what you’re asking for. So you’ll be more likely to have longer conversations with them, making sure that you’re both on the same page. But as you grow more comfortable with your freelancer, conversations start to go more like this:

“Hey designer! We have a big event coming up and we’d like to make a new t-shirt for it. Can you help us out?”

“Sure. When is the event?”

“Next month. It’s a big Mardi Gras extravaganza. I’m thinking something that ties in a crown.”

“Yeah, sure. Sounds good. I’ll start some sketches.”

Yikes. How much is the designer going to charge? Is this shirt just a front? Just a back? Front, back, and some sleeve art? When is the design due? The client needs enough time to get the art over to the t-shirt vendor so the shirts can actually be made. When does that need to happen?

Before anyone starts work, both parties should know:

  • What the client wants. If they want a website, the client and freelancer need to have a long chat about the function and purpose of this website.
  • How many the client wants. How many photos, words, drawings, website pages, whatever. “Some” is not good enough. “Some” could be 6. It could also be 60.
  • How much the client is going to pay, AND how much additional work will cost. The agreement may be for a 6-page website, but it’s very easy to forget something and decide to add it on the back end. It happens all the time. Freelancers should relay the costs for extra work. Planning for these costs ahead of time can help to prevent scope-creep for the freelancer or a shocking bill for the client.

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!

Be Clear About Ownership

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

I knew someone 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 on 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. If a transfer needs to be made, do it in writing!

Context is Key

Freelancers need to know what the deliverable is, but they also need to know you — your likes and dislikes, the company’s vibe, where this project fits in with other projects.

Without knowing the full context, it can be really hard for a freelancer to deliver what you want. For example, say you want to hire a designer to re-design your logo. What didn’t you like about the old one? What problem are you trying to solve with this new design? What do you want the logo to convey? Are there any colors that you want to keep, or any colors you hate? Do you have strong feelings about Comic Sans? The designer needs to know!

Without the full scope, you won’t get what you’re looking for, so you’ll be unhappy. Then you’ll write a long, detailed email with feedback for the freelancer — all information that they should have had before they started in the first place. They’ll have to do the job twice, so they’ll be unhappy.

I just want everyone to be happy.

Don’t be Afraid to Provide Feedback

So I know that three sentences ago, I said a long email of client feedback is a bad thing. That’s only when it’s information the client should have provided from the get-go.

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 product for a day or two to gather your thoughts. Try to hone in on exactly what’s bothering you. 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.

Creative work is collaboration. We’re 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.


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.

First Job = Small Job

When starting a relationship with a new contractor, start small. Make sure you like each other and work well together before you go all-in on something massive and expensive.

Maybe hire a content writer to do a blog post 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 $50 project than a $500 project!

Get it in Writing

Work Better with Freelancers by Signing a contract


Signing in blood is optional.

All of those details that you hashed out in the “All the details, all the time” section? Get. Them. In. Writing.

An email is good. A contract is better. It doesn’t have to be anything fancy! Just list out the deliverables, the deadline, and the payment plan. Then you both sign it. Boom.

If you want to get a lawyer involved, go for it. But even a basic agreement that you or the freelancer draws up is better than nothing. A basic document that you can both refer to will help prevent misunderstandings or confusion down the line.

This concludes my ABC(DEFG)’s of how to work better with freelancers. There are a lot of us, and there will only be more as the gig economy grows. Master these methods, and you’ll be hailed by all as the freelancer-whisperer.


Want to work with me? Tell me what you need!

Some tips for how to communicate with your freelancer pals to keep everyone happy.

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