This seems like it goes without saying, but do hire a freelance writer with good grammatical skills. And by “good” I don’t mean, “correct twenty years ago” good. I mean good right now. Respectful and inclusive now. Current. Fresh.
Hiring a freelance writer who knows the rules, when to break those rules, and when to use newly adapted rules will result in a better outcome. Grammar and mechanical (things like spelling, capitalization, and punctuation) errors are one of the more unforgivable sins in written communication, and when your readers notice the errors, your message takes a backseat to the missing period or the typo in your title. You lose credibility. Part of the problem is that the grammatical rules are different for varying audiences.
It’s especially helpful if you can let your freelance writer know the demographics of your intended audience. Skilled freelance writers can even re-write the same piece so that you can use the same ideas written specifically for various target audiences.
For example, if you are hiring a freelance writer to create the copy in a half-page mailer, and you are going to send these out all over town, your freelance writer can construct the copy with your largest demographic in mind, let’s say that’s 25- to 45-year-olds. That copy may use sentence fragments and non-traditional pronouns because that audience will overlook those as grammatical errors; however, your freelance writer will be able to re-write the same copy with your 46- to 75-year-olds without any fragments and with traditional use of pronouns because that is more aligned with what that audience expects. And if any segment of your audience speaks English as a second language, a skilled freelance writer will know to leave out idioms that don’t easily translate word-for-word, such as “call it a day” or “by the skin of your teeth.” Each audience will be better able to receive your message rather than getting caught up on the grammar in your mailer.
Another consideration is that some aspects of writing have only one legitimately correct way of being presented. Take citing a quoted source, for example. Knowing the difference between APA and MLA goes a long way. Very few people memorize all the rules of various types of citation, but contrary to popular belief, you can’t just pop the information into easybib.org or look it up in a reference book and get 100% accurate results. New editions are often constructed for citation styles in order to encompass the ever-evolving technology and a changing language. It’s best to hire a freelance writer who is well-versed and up-to-date with citation styles.
Not only do times and versions change with citation styles, but times have changed (finally!) with the respect given to various genders. If your target audience is clued in on the fact that humans can’t be categorized with a simple binary system of pronouns (and I hope they are aware of this), they will expect you and your freelance writer to be not only aware, but also considerate of this. Using a sentence such as, “Your reader has ways of telling if he or she can trust you,” alienates people, yet it is grammatically correct if you are using old-school grammar rules. New-school grammar rules let you be more inclusive. Therefore, you can write, “Your reader has ways of telling if they can trust you.” To match up the antecedent “reader” which is singular, with the pronoun “they” which is plural would have been a no-no to look out for when hiring a freelance writer twenty years ago, but now, most of your readers expect you to be respectful and break that rule.
There are many more ingredients that go into relevant grammar and mechanics, but one last important aspect to discuss here is word choice leading to tone. If you can find a freelance writer who is willing to communicate with you enough to learn your desired tone and to stay true to that tone by selecting the right words, rather than foisting their tone on your project, your audience will sense the cohesion between your product and your ad copy, the cohesion of your company and your newsletter, or what have you. (More on this in Session #3).
Even if you and your freelance writer are not able to communicate face-to-face regarding your desired tone, there are many ways to meet asynchronistically or virtually. Sincere, effective working relationships develop all the time through use of video chats, emails, and other virtual means. In fact, you may get more out of your freelance writer if you can spare them the commute and use what would have been drive-time to video-chat more about your intended tone, target audience and written product.