Reflections

5 mistakes to avoid when working with content freelancers

Will Gibbens
Contentoo Freelancer
6 min read
May 2, 2025

Ever briefed a freelancer, only to get content back that totally missed the mark?

Maybe the tone was off. Or the structure was wrong. Or the deadline got pushed… again.

If that sounds familiar, you’re not alone. While 75% of companies work with freelance content creators, many are still figuring out how to get the most out of that partnership.

Done right, freelancers bring speed, flexibility and niche expertise to your content strategy. Done wrong, you end up wasting time, budget and patience.

In this guide, we’ll unpack 5 of the most common mistakes companies make when working with content freelancers—and more importantly, how to avoid them. And at the end, we’ll share one bonus tip to help you simplify your processes and scale your entire content production process.

Why hire freelancers?

There are lots of good reasons why freelance content creation has become a mainstay of digital marketing. Outsourcing gives you access to specialised experts who can fill gaps in your team or simply allow you to create compelling content faster, leaner and more cost-effectively.

Working with freelancers should be a relief and a benefit to your busy team. But it takes a careful approach to get the results you want. If you approach it without a clear plan, things might get bumpy. Fortunately, all it takes is some preparation and a few best practices to make sure you’re seeing value with every project you outsource.

Mistake 1: Improper vetting

The freelance talent market is booming. On the bright side, that means you have lots of options when shopping for freelance talent. On the other hand, it can be overwhelming, especially if you’re not sure what to look for.

Many companies rush through the selection and vetting process and simply go with the first available freelancer who seems ‘good enough’. But skill level, industry familiarity, tone of voice and even time zone can make or break the collaboration.

Read: What dating apps can teach us about finding the perfect freelancer

How to avoid it:

  • Always have an introductory call with your freelancer to get to know them, align on strategy, and get a sense of what collaboration will be like.
  • Ask for writing samples relevant to your industry, product and preferred content formats.
  • Run a paid pilot project to test the freelancer’s talent.

Fun fact: Our talent team pre-vets every freelancer in our network for writing quality, tone of voice, and industry expertise, so you don’t have to spend hours searching.

Mistake 2: Unclear goals and expectations

You may think that since freelancers aren’t actual employees, they don’t really need to be involved in your strategy, or completely informed of your goals to deliver what you need. Think again! Without clarity on your standards and expectations, freelancers can really only guess at what you want from them.

In our experience, freelancers are much more invested in their projects and deliver better quality when they feel like they’re part of your team. Without that shared sense of purpose, you’ll probably have to spend a lot of unnecessary time revising or even rewriting content that’s not on-brand, or simply not aligned with your goals.

How to avoid it:

  • Onboard freelancers and give them a clear intro into your current strategy, goals and target audience.
  • Share style guides, tone of voice documents and branding information with them.
  • Give them examples of the quality you expect them to deliver. For example, show them your top-ranking blog posts or competitor content that you want to outperform.

Fun fact: Our dedicated account managers will match you with freelancers and help with a full onboarding and give access to your strategy, brand guidelines, and audience insights from day one.

Mistake 3: Weak project briefings

A strong, well-structured project briefing is also essential. It sets the tone for the entire project, so the more direction you provide, the better the results will be.

When you provide a detailed, thoughtful briefing, the freelancer also picks up on how important the project actually is to you, which motivates them to deliver better quality. Weak, unclear briefs will often wind up costing you more time answering questions or revising the content after the fact.

How to avoid it:

  • Use a standardised briefing template and process, so you never leave out any important information.
  • Give your freelancer easy lines of communication, so they can quickly message you to discuss the project and stay in sync.
  • Have a clear vision of what you want the content to look like, and share this with your freelancer (including a rough outline, keyword focus, CTA and more).

Fun fact: Our built-in briefing makes it easy to share the right info every time, from structure and tone to keywords and goals.

Mistake 4: Poor communication and feedback loops

Freelancers rely on your input to deliver what you’re looking for. That’s why you need easy and efficient ways to exchange high-quality feedback with them.

The best freelancers are highly in-demand, and prefer to avoid lengthy, chaotic back-and-forth by email. They know that clients who work with manual workflows are less mature in their content marketing strategy, which is a red flag for them. They thrive on content management platforms that give them a clean overview, standard feedback and revision workflows, and instant messaging that makes it easy to communicate with you. 

If you force your freelancers to communicate via email—or if your feedback process is unstructured or unclear—you risk wasting time and even damaging the working relationship in the long term.

Free download: better ways to give and get feedback

How to avoid it:

  • Use standard, automated workflows for handling different document versions, so your freelancer doesn’t have to dig through email threads.
  • Avoid “drip-feeding” feedback. Collect all stakeholder feedback into a single document before returning it to your freelancer so they can work more efficiently.
  • Keep your feedback specific, constructive and focused on the project goal.

Fun fact: Skip the back-and-forth Slack/email chaos. Our platform has integrated messaging and structured feedback workflows, so everyone stays in sync.

Mistake 5: Micromanaging or overloading freelancers

Sure, it’s important to give your freelancer lots of guidance, just remember that they thrive on freedom and creativity. The more autonomy you give, the more original and engaging the content will be.

Resist the urge to take too much control over the freelancer’s creative process. You’ll also want to avoid bombarding the same freelancer with too many projects all at once. The best freelancers serve tons of clients and may not always have space for last-minute projects.

How to avoid it:

  • Spread out your projects to multiple freelancers who are all part of your network and know how to deliver the quality you need.
  • Guide them on your company’s tone of voice, so they can put their creative ideas into language that sounds just like your brand.
  • Encourage them to be creative and toss around ideas.

Fun fact: We match you with a full team of freelancers who know your brand, so you can scale content without overloading a single writer—or yourself.

Bonus tip: Outsource the easy way with a content management platform

Managing freelancers may sound like a lot, especially if you’re just getting started. We get that, which is why we’ve come up with an easy way to avoid mistakes and get the most out of it. Our platform was built by and for marketers, so it covers all your bases.

Need help finding the right freelancer? There’s no need to spend hours scrolling LinkedIn. Every freelancer in our network is carefully vetted, and we automatically match you with the right talent for your needs.

Once we’ve matched you with the content creators you need, our platform gives you simple workflows that keep your projects moving. You never have to worry about email back-and-forth, briefings-gone-wrong or feeling out of touch with your freelancer. Our simple flow, detailed briefing templates, and direct messaging keep you in sync at every stage of the project.

Plus, when you need to scale up your content output or shoot over a last-minute briefing, there are hundreds of freelancers in our network ready to help.

Key takeaways

  • Collaboration is the key to getting more out of outsourcing content to freelancers.
  • Many freelance content projects get derailed by poor communication, misalignment and weak briefings.
  • A content management platform makes collaboration easy, so you avoid costly mistakes.

Boost your brand’s impact with content freelancers

Freelance content creators can be your brand’s best-kept secret. All it takes is the right tools.

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