Working with Contractors Part 2: Mistakes to Avoid (and What Not to Assume)

If you’ve ever hired a creative contractor and still found yourself answering a dozen last-minute questions the night before your concert, you’re not alone.

In Part 1 of this series, we talked about setting up a strong foundation with a Brand and Marketing Toolkit—your one-stop cheat sheet for getting contractors aligned with your chorus’s tone, look, and goals.

Now it’s time for the next step: avoiding the assumptions and oversights that can throw a wrench into even the best of working relationships.

Whether you're hiring a social media freelancer, a graphic designer, or a marketing strategist, here are some common mistakes to avoid—plus practical fixes that will make life easier for both you and your contractor.

1. Don’t Assume the Scope is Obvious

Let’s say your contractor creates a gorgeous social media graphic for your season announcement. You love it! But… why hasn’t it been posted?

Here’s the catch: unless you’ve clearly stated in your agreement who is responsible for publishing content, don’t assume they’re managing that part.

Some contractors are content creators only (they make the stuff, you post it). Others may also offer scheduling and publishing, but you have to spell it out.

Be explicit:

• Will they be posting, or will you?
• Are they expected to manage DMs or comments?
• Is inbox monitoring part of the job?
• Who fields questions from the public, and when?

Set clear boundaries around tasks—what’s included and what’s not—and you’ll save everyone a lot of confusion (and follow-up emails).

2. Get It in Writing (Even if it’s Simple)

Before any work begins, have a written agreement in place. No, it doesn’t need to be a 15-page legalese monster. A one-page Memorandum of Understanding (MoU) will do the trick if that’s more your style.

Your contract should include:

• Deliverables (what’s being created)
• Timelines and deadlines
• Compensation (flat rate, hourly, retainer, or per deliverable)
• Number of revisions included
• Invoicing/payment terms
• Points of contact

This protects both parties, clarifies expectations, and helps avoid scope creep (which nobody enjoys—especially on a tight nonprofit budget).

3. Be Realistic About the Learning Curve

Contractors aren’t mind-readers. Even the most seasoned creatives will need a little time to get to know your organization’s voice, audience, and quirks.

Expecting someone to perfectly embody your chorus’s tone overnight isn’t fair to them—or to you. This is where your Brand & Marketing Toolkit comes in handy (and why Part 1 exists!).

Give your contractor a warm runway to get familiar with your materials. The better the onboarding, the better the output.

4. Clarify Communication Preferences Early

How do you prefer to communicate with your colleagues to work effectively? Consider this before you begin working with a contractor. Do you prefer multiple short emails or one batched message? Can they text you? Should Slack be used for quick updates or only emergencies?

You don’t need to over-engineer communication—but a short chat at the start of your working relationship can go a long way.

Bonus tip: Share your “office hours” so both sides know when replies can be expected (and when it’s totally fine to unplug).

5. Define Who Owns What (a.k.a. Intellectual Property Rights)

Here’s a surprisingly murky area: Just because you paid for a design doesn’t necessarily mean you own it in the legal sense.

That’s because—unless otherwise stated—contractors typically retain the copyright to their work. (Yep, really!)

You can ask for a “full rights transfer” or a “work-for-hire” agreement in your contract if ownership matters. Or you can simply clarify that you have unlimited usage rights, even if the contractor keeps portfolio credit.

Speaking of which…

6. Give Contractors Permission to Showcase the Work

Most creatives want to show off the cool work they did for you—and it benefits you too (hello, extra exposure!).

Make it easy by including a simple line in your agreement that allows the contractor to use select deliverables in their personal portfolio, website, or case studies. This prevents them from having to ask later—and helps maintain a good professional relationship.

7. Make Sure Everyone Knows How Payment Works

Contractors are small businesses. Clear, prompt payment is a sign of respect—and good planning.

Let them know:

• How often will you pay (per project? monthly?)
• Which payment methods you use (direct deposit, check by mail, etc.)
• If you need a W-9 and/or an invoice to process payment
• Who to contact if payment is delayed or questions come up

If your organization has a slow or multi-step accounting process, be upfront. Most contractors can accommodate delays if they know what to expect.

TL;DR – Clear Is Kind

When in doubt, spell it out. Don’t leave your contractor guessing about scope, deadlines, or deliverables. It’s way easier (and friendlier!) to have clear expectations from the start than to unravel assumptions later.

And if you’re still working out what kind of support your chorus needs—no problem! You don’t have to get it all right on the first try. Every contract is a learning opportunity.

You’re building a team. A partnership. A creative collaboration. And that takes thoughtful communication, mutual respect, and a bit of trial and error.

Got any contractor tips or “oops” moments to share? Leave a comment below—we’d love to learn from your experience!