4 Signs Your Company Should Break up with a Freelancer


How do you know when a freelance writer is worth keeping? It comes down to more than their writing chops. A great mix to look for includes responsiveness, attention to detail, a collaborative spirit, and a dash of humility.

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A great freelance writer can be a tremendous asset to your company and a long-term partner who helps keep your marketing motor running. Contract help is, by and large, more affordable than hiring full-time employees. It’s more flexible too.

During the pandemic and the rise of another recession, workforces across the world have found themselves needing to cut overhead. Increasingly, companies are catching on to the contract model rather than hiring more full-time employees.

A stellar writer will save you time and money while serving up valuable content and resources to your audience—which opens the door for them to become an extension of your core team. But less-than-stellar freelance work will cost you money and massive amounts of time.

So as you search for reliable help, are there any red flags you should look out for? After years of working with freelancer writers, I’ve discovered four common issues that signal someone may not be the best choice.

Red Flag #1: They don’t respond in a timely manner

Timely communication is critical to the success of your content marketing efforts. If a freelancer’s responses routinely come with delays, it’s worth noting the pattern that’s forming.

Barring an emergency, unresponsiveness early in a relationship could mean a couple of things. The writer may not be that excited about the work, or they could be too overloaded with other projects. In either case, the writer is likely not in a position to offer you their very best efforts.

Pro Tip: Be clear with your expectation of promptness from the start. Consider establishing a “timeliness guideline” as a standard (like, 48 hours during the work week) for everyone to follow.

Red Flag #2: They procrastinate and miss deadlines

It’s very difficult to produce good work at the last minute, even though many of us feel we work best under pressure. Like all things, good writing requires planning and research—and that’s before it comes in house for edits.

What should you pay close attention to? Listen to how they talk about project management when you meet with them. For example, if a freelancer mentions they tend to juggle lots of projects and pull all-nighters, that could throw off your content calendar down the road, signaling they may not be the best fit for you long term.

Pro Tip: Use a project management tool to help track progress and streamline communication, and consider setting milestones. Communicate early that someone from the team will be checking in (depending on length, maybe a day or two before deadline) to see how thing are going and if there are any questions or feedback along the way.

Red Flag #3: They frequently reject assignments

Do you have a freelancer who you’d love to work with, but they never seem to be available?

This is when setting expectations is crucial. When someone routinely turns down your assignments, ask them to have a larger conversation about what work scope and interests. If you need a consistent contributor but a freelancer is only available for the occasional one-off, it might be time to move on. They could be really busy, or they’re politely telling you they’re not a good fit.

Pro Tip: Many freelance writers book work at least a month out, so they know what they’ve got coming in. If you make a content calendar well in advance, set up an agreement with the writer so they can save room in their schedule.

Red Flag #4: They push back on your company’s processes

You have an established workflow that works for you. When you onboard a new freelancer, it’s important to explain the process and people involved so the freelancer knows what to expect. It’s also important that you give them any relevant materials, like style guides, brief templates, tech access, etc.

If a writer ignores these, pay attention. It could signal more trouble down the road if they’re unable to follow your established system, and the editing and feedback process may prove difficult down the road. It’s important to work with someone who’s flexible to adapt to your company’s existing workflow. This will lead to more efficiency and less administrative headaches for you.

Pro Tip: Before you move on from anyone, be sure to have a conversation to figure out what’s behind any process issues. It’s possible that, as they’re learning you and you’re learning them, something got lost in translation.

Remember the four flags

Your ideal freelancer is out there. As you work with new contractors, it’s important not to be totally enamored with them on the first meeting. Be sure to keep an eye on these red flags—otherwise, you may find yourself strapped to a freelancer you’re ultimately unhappy with.

But if you keep your eyes wide open when working with a new freelancer, you’ll set yourself up for successful relationships with your freelance writers. And that can serve your company major long-term dividends.



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