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Grammar, syntax and bears oh my! How to select solid writers in the wild.

As we’ve said before, in an online world "your audience will examine you through the lens of your content before ever having made your acquaintance.” And they will judge you. Imagine that you’re a web designer outsourcing the content of a site or you’re a business owner looking for someone to get your company’s message across. Whatever your goal, take care and pay close attention when picking a content writer because they alone will guide the lens through which you will be judged. So what should you look out for?

When you hire someone, it’s likely you’ll rely primarily on written communications to identify your pick. If you’re looking at anything beyond a very small project, it’s advisable that you also speak to top candidates over the phone or via video chat. This will allow you to get a better sense of who they are. That said, you can learn a lot about someone if you pay attention to some key indicators in written communication. First of all, ask yourself: are we understanding each other? What we mean by this is that when you communicate, you both have a clear sense of the other’s expectations and there are zero or few misunderstandings. Both the writer and the client should be working together to gain clarity, this shouldn’t weigh entirely on the client’s shoulders.

Everyone hates dying by deadlines. Mad sprints to reach the finish line on time are something we all want to avoid as much as possible. The last thing you need is to hire someone that will keep tripping you up. If the writer seems to be content leaving things up in the air when you’re emailing or messaging, that’s not a good sign. Things like “I’ll get it done” may sound good, but “I’ll get it done within the next couple of days” is preferable, and “I’ll get it done by end of day tomorrow” is even better. Next, ask: are they responding to emails promptly? We wouldn’t expect anyone to be glued to their inbox, but do consider it essential that they get back to you within a day during the work week. If you’re not getting timely responses when they’re still trying to land the job, it does not bode well for a future work relationship.

Grammar, syntax and readability may not be the most important things when it comes to connecting with your client base, but they are crucial in that if you fail at them most people won’t take you seriously. With this in mind, be sure to read at least two samples of your candidates’ writing. Best practice would be to request a sample that is in line with what you will eventually need them to produce: if you’re looking for technical content, reading an essay will obviously do you no good. If they don’t happen to have anything pertinent to your business, it’s legitimate to ask them to write a brief paragraph of around 150 words on a specific topic of your choice.

When reading samples, if you see a “they’re” where a “their” should be, that’s not just a red flag - that flag is on fire. Everyone can miss something once in a while, but a couple of these really add up - same goes for “ad” instead of “add”! As for readability, your writer has to produce text that flows well. Since most readers sub vocalize when they read (i.e. they have an internal voice reading the text word by word in their head), any clunky language or word repetitions can trip them up. An example of this? “I think we should change our thinking on this.” In addition to this, be sure to ask yourself whether you’re engaged by the text. Keep in mind that reading it is part of your job right now: you have a natural interest in what you are reading. Try to read from the perspective of a third party that may not share your knowledge or interest when it comes to the topic at hand. Reading the sample text doesn’t have to make someone jump out of their seat in excitement, but their eyes can’t be glazing over either.

Some people believe that an ideal candidate requires experience in your market. We agree. Working with a writer that has a feel for the competition can’t be a bad thing. Yet working with someone that does not have experience in your niche, but is adept and has transferable skills, can also work out well. It will depend on your industry, but it’s more likely than not that this type of writer could bring new ideas and enthusiasm to your content. You don’t want to publish the same rote things that your competitors already have.

Always inquire about a candidate’s schedule and work processes. Does their availability fit your needs and timelines? Are your working processes compatible? These questions are fundamental, especially if you are looking at working with someone long-term. Working within your budget is also obviously imperative, but you have to acknowledge that quality will always to a great extent be dependent on price. If you can afford to, don’t pick someone because they cost half the price of your top contender. Recurring to low-cost freelancers and content mills will either be noticeable in your end product or it will add on to your own workload. How? In the form of ambiguous emails, missed deadlines and being left with content that may be riddled with errors and may not even be in the ballpark of what you asked for. You’ll end up either looking for a new person or doing extra work yourself. Either way that involves wasting time and money.

We hope that following this advice will land you a tailor-made content writer. If you find yourself hesitant, or going back and forth between a couple of applicants, the best approach will always be to choose someone who has proven their worth and whom you feel you can trust. You can award a candidate extra credit if they have displayed insights into your business that you’ve overlooked. That’s always great, as it’s the mark of someone with analytical skills. Those are indicative of a writer that will know how to speak to your audience. A good content writer should act as the ambassador of your intention and work to extract maximum value. Great content writers can direct you to sources and ideas that will not only crystallize your intention, they’ll also take you down a path that expands the thought in a way you never imagined.

Also note that you’re not going to get the same level of dedication from a large company than you would from a single writer or a small agency. The added bonus of the latter is that, as there is more than one person, you can benefit from accountability structures and still not get lost in a sea of clients.

Whatever you do, be sure to lay out your goals and expectations clearly and from day one. If you follow our tips above we're sure you'll be on your way to a great partnership!

If you’d like to know which questions we ask our writers during their interview process, send us a quick note and we’ll share them with you.


  • Everyone lives online now - you will be judged by your content.

  • Try to speak with your top candidates over the phone or via video chat.

  • Pay attention to your written communications:

  • Are you understanding each other?

  • Is the candidate responding promptly to emails?

  • Ask for writing samples and look out for potential grammar/syntax issues.

  • If their samples don’t fit your needs, you can assign the candidate a brief piece - approx. 150 words.

  • Consider the readability of their writing - most readers sub vocalize and get tripped up by clunky language and poor phrasing.

  • A writer that lacks experience in your niche but is skilled may turn out to be an asset.

  • Ask the candidate about their schedule and work processes.

  • If you go with the cheapest option available eventually your timeline, product and pocket will suffer. Go for the best option within your budget.

  • Lay out your goals and expectations clearly from day one.

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