Hiring your first freelancer (and how to work with them)

Let’s be real: saying "I need help with content" is like walking into a restaurant and asking for "food." Be more specific. Are you looking for:

• A social strategist to build the game plan?

• A content creator to film and edit reels?

• A copywriter who can make your email open rates soar?

• A graphic designer to bring your brand to life?

Think about what you're trying to solve, not just what you want made.

Do you need higher engagement on socials? A refresh on your visual identity? A consistent blog cadence? Write out your dream list of deliverables, along with what success looks like for each one. The more specific you are, the better your chances of finding someone who can actually help you get there.

And remember, according to Genius.com, 77% of the arts and design industry is freelance. So yeah, the talent is out there—you just need to know exactly what you’re hiring for.

Okay, let’s talk about money. Freelancers are professionals, not bargain-bin employees. Respect their craft and budget accordingly.

Some rough benchmarks:

• Copywriters: $0.20–$1 per word or $50–$150/hour

• Video editors: $50–$100/hour or $300–$1,000/project

• Graphic designers: $40–$120/hour

• Social media managers: $500–$2,000/month

The average hourly freelance rate in the U.S. is $47.71, but expect to pay more for niche skills, lightning-fast turnarounds, or top-tier quality.

When setting a budget, consider not just the output—but the impact. A cheaper freelancer might cost less per hour, but if it takes twice as long or needs constant revisions, are you really saving?

Your budget should reflect what you want: speed, quality, reliability, or all three. Be upfront about what you can afford, but leave room for negotiation based on experience and complexity.

Nobody wants to apply to a job that reads like a legal document. If your vibe is fun and fast-moving, let that come through.

Include:

• Who you are and what you do (quickly!)

• What you need help with (specific deliverables)

• The timeline or monthly commitment

• Your budget or budget range

• What kind of freelancer you’re looking for (personality, tone, work style)

• Why working with your team is a great perk!

A strong job description filters out the wrong candidates just as much as it draws in the right ones. Don’t be afraid to get quirky or niche—if your brand has a strong tone or values, let those shine.

For example: “We’re a digital publication covering music, fashion, and culture. Looking for a witty, punchy writer to handle 3–4 articles per m

Portfolios are helpful, but they don’t always tell the full story—especially when it comes to how someone will collaborate with you. That’s where a short test assignment can come in handy. But let’s get one thing straight: freelancers are taking time out of their day, using their brainpower and skill set for your brand. That deserves respect.

If you do choose to assign a test, you could choose to pay them for their time. That could be a flat rate for the project, an hourly payment for however long the task should take, or even a small thank-you gift card if your budget is super tight.

Some companies even let candidates choose between a gift card or a small honorarium—either way, it shows you value their effort.

And most importantly? Be very clear that you won’t be using their test assignment in any real, live campaigns. Remember, this isn’t a loophole for getting free creative work. Make sure they know this is purely for evaluation, and not something that will end up in your newsletter or on your homepage.

A fair, thoughtful test does two things: it gives you insight into how someone works under your brief—and it signals to freelancers that you’re a respectful, stand-up client. In a sea of more than one-third of U.S. workers freelancing, that kind of professionalism goes a long way.

You don’t necessarily need a formal interview process. But you do need to make sure you’re aligned on more than just the brief. A quick 15-minute video call can help you:

• Talk through your project and see if they ask smart, thoughtful questions

• Set expectations for how you’ll work together and what collaboration looks like

• See if the vibes match (because yes, vibes absolutely matter)

Think of this as your creative chemistry check. Use the call to explore a few “what if” scenarios—like what happens if timelines shift, or how they prefer to receive feedback.

Are they more “drop comments in the doc” or “let’s talk it out on a quick call”? This is also a chance for them to ask you questions, which is a good sign they’re serious about doing their best work. Ideally, the conversation feels easy.

You want someone who gets your tone, understands your goals, and communicates clearly. This is your future partner-in-creation—not just a one-and-done vendor.

So you’ve found the freelancer you want to work with for your project. Now what?

Before any work kicks off, take a few minutes to align on the logistical stuff that can make or break a working relationship:

• When do you expect deliverables to be turned in?

• How quickly will you provide feedback?

• What does the revision process look like? One round? Two? Are there hard limits?

• How will you communicate—Slack, email, a shared doc, or another platform?

• What’s the plan if something goes off schedule?

These might sound like minor details, but getting them sorted upfront saves you both time and stress down the line. Every freelancer works differently, and every client does too.

Maybe they’re juggling multiple projects and need feedback within 48 hours to keep things moving. Maybe you need end-of-week check-ins to report to your team. Establishing your cadence early helps everyone stay on track and avoid awkward follow-ups.

And remember: freelancers now make up 25% of the workforce at many companies. That’s not a side hustle—it’s a real part of your business. Set the foundation like you would with any other teammate.

Contracts don’t need to be scary. You’re not lawyering up—you’re just getting aligned. A contract just puts expectations on paper so there are no surprises later. It’s about clarity, not complexity.

At a minimum, include:

• Scope of work (what’s being delivered and when)

• Payment terms (when and how they get paid)

• Timeline and deadlines

• Revision policy (how many rounds, how long they take)

• Ownership rights (who owns the final product and when)

Even for a one-off project, a simple contract shows you’re organized and respectful of their time. It gives your freelancer confidence that you’re serious, and it gives you peace of mind that you’re both on the same page. Plus, it helps avoid sticky conversations down the line like “I thought that was included…”

Plus, you can use tools like HelloSign or DocuSign to keep it digital and painless!

Don’t just toss them a Google Doc and hope for the best. Freelancers aren’t mind readers—and they’re not part of your daily team meetings. That’s why onboarding matters. If you want great work, you need to give them the tools and context to create it.

Here’s how to set them up for success:

• Share your brand guidelines and tone of voice (bonus points for examples of what not to do)

• Provide sample work or inspiration that reflects your style

• Give them access to the right tools, logins, or systems

• Introduce them to collaborators or internal team members they’ll be working with

A solid kickoff makes everything easier. Freelancers who understand the “why” behind a project will deliver better “what.”

You don’t need to handhold—but you do need to hand over the goods that help them hit the mark. Treat onboarding like a mini welcome party, not a formality. Because when freelancers feel supported, they do their best work.

Most, if not all, freelancers don’t need hand-holding. But they do need structure and clarity. You’re hiring them for their expertise, not to shadow you on every move. But that doesn’t mean you can vanish into thin air either.

Here’s what striking the balance looks like:

• Set weekly or biweekly check-ins (even a quick email update counts)

• Keep project management tools up to date so they’re not left guessing

• Give feedback that’s specific and actionable—not “make it pop,” but “this needs more contrast”

Once expectations are aligned, give them the space to do their thing. Let them work their magic. But also, be present enough that they don’t feel like they’re creating in a vacuum. Freelancers thrive when they’re trusted and supported. And just like any team member, they do their best work when communication flows both ways.

Ghosting your freelancer until the next urgent deadline? Not the move. Be consistent. Be responsive. Be someone they’re excited to work with again.

Look, we get it—sometimes accounting departments have their own timelines, approval chains, and mysteries. But here’s the thing: freelancers rely on timely payments the same way salaried employees rely on their paycheck. Except freelancers don’t have payroll. They are their payroll.

When you agree on payment terms—whether that’s net 14, net 30, or payment upon delivery—stick to them. Ideally, keep it under two weeks. The longer you wait, the more you risk burning trust. And word travels fast in freelance circles.

If you’re working with a finance team or an external bookkeeper, build in time for approvals and send reminders proactively. Better yet, set up an easy process for recurring freelancers so they’re not chasing you every month.

Paying on time shows respect. It tells your freelancer: “Your time matters. Your work matters. We’re in this together.” And yes, tossing in a short thank-you email or even just a “great work on this” goes a long way toward building a real relationship—one where they want to work with you again.

Freelancers remember how you treat them. Pay them late, and they might not come back. Pay them promptly and treat them like a partner, and they’ll bring their A-game every time.

Once you dip your toes into the freelance pool, it can turn into a full dive pretty quickly. One minute you’re hiring someone for a one-off blog post, the next you’ve got a go-to copywriter, a part-time podcast editor, a designer on retainer, and a virtual assistant managing your inbox on Mondays.

This is exciting—but without a system, it can get chaotic.

You need a way to keep track of:

• Who does what (and how well)

• Who’s available when

• What tools they need access to

• Where they are in your workflow

• Past deliverables and performance notes

Spreadsheets and sticky notes will only take you so far.

That’s where a customer relationship management (CRM) platform like Copper becomes your secret weapon. You can tag freelancers by specialty (design, copy, video, etc.), store notes about project history and working style, track current assignments, and even flag folks you’d like to bring back for future work. Think of it as the easiest way to manage and organize your freelance roster—fully searchable, totally centralized, and way more efficient than searching your inbox for that one email from “awesomewriter@gmail.com.”

The more freelancers you bring on, the more essential it becomes to have an organized system. Because when you know exactly who’s available, what they’re great at, and what they’ve done for you in the past, assigning work becomes effortless—and scaling your team becomes second nature.

Take stock:

• Did they deliver on time and on brief?

• Was the communication smooth?

• Would you hire them again?

If yes—keep their info handy. Save their contact, rate, and what kinds of projects they’re great at. In fact, once you’ve worked with one reliable freelancer, you might realize you’re ready to bring in a few more. Maybe a designer to support your new writer, or a project-based video editor to help with marketing campaigns.

Suddenly, you’ve gone from "just needing a little help" to building your own freelance A-team.

That’s when having a system becomes a must-have, not a nice-to-have. As your bench of go-to collaborators grows, organizing who does what, when they’re available, and how they prefer to work is key to keeping things moving without the chaos.

And if the relationship doesn’t work out? Don’t ghost them. Be honest and kind with your feedback. Let them know where things didn’t align and thank them for their time. It’s better for everyone, and it keeps your reputation solid in the freelance community.

Every freelancer you work with helps define what your ideal collaboration looks like. And when you find your people, nurture that connection. The best freelancers become long-term creative partners who elevate everything you do—and make scaling your business feel seamless.

Get to hiring!

Hiring your first freelancer is a big step—but it doesn’t have to be a stressful one. Be clear, be respectful, and treat them like the pros they are.

A freelancer isn’t just someone who checks a box—they’re a collaborator, a creative partner, and a key to helping your business grow without the overhead. Do it right, and you’ll wonder why you didn’t start sooner.

And when you’ve got five freelancers running at once and you need to stay on top of deliverables, timelines, and who does what? Copper keeps it all organized—so you can get back to doing the fun stuff. Try it now for 14 days for free!