Recently, I published an article on LinkedIn that describes what are, in my opinion, some of the most important questions you can ask when you’re interviewing freelancers for writing content. In all honesty, there probably is no single “best” set of questions, because it’s highly dependent on what you want from a writer and on what your priorities are. It’s not the questions themselves that are good or bad; it’s more a matter of whether the questions will provide useful, relevant answers. So I thought I’d do a quick check of what other sources have said — and, boy, are there some differences! Here’s a roundup on some of the most common advice (minus any duplicates from my own list) and my take on whether that question will garner you any actionable information:

Which blogs do you read regularly?

I get the point — you want to know that the writer knows what’s going on in the world of content creation — but it’s not the right question. Personally, I don’t believe that any single source (myself especially!) has all of the right answers. There are no blogs I read regularly. Instead, I have a Twitter stream set up for content marketing, and I read what looks interesting and/or what is trending. A better question would be, “How do you stay on top of the latest developments in content marketing?”

May I see some writing samples?

This is not a useless question; you’d be negligent not to ask for writing samples. But you should review them with the understanding that you have no idea how much editing was done between what the writer submitted and the final copy. You could ask the writer to describe any edits that were made on a particular piece, but I wouldn’t discount a writer who couldn’t tell you. I churn out a lot of stuff; sometimes I can tell when a single word has been changed, but not always.

Tell me about the best book you’ve read recently.

Again, I  understand the purpose: The way you perfect your writing is by reading. But the question just doesn’t provide any information that’s actionable. Are you sure a writer who just finished “War and Peace” can do a better job than someone who reads the tabloids? It’s a good supplementary question, but it should never be the deciding factor.

Do you know how to optimize your content for search engines?

Who’s going to say no? Besides, unless Google gets tired of changing their algorithms, there’s no one right answer. A more meaningful question would be, “Tell me about SEO.” You’d gain insight into both what the writer knows of current practices and how they stay on top of changes.

Describe the proper layout and format of a blog post.

This one has me scratching my head. If there’s a single proper layout and format, nobody has let me in on the secret.

Which professional organizations do you belong to?

This is another one that’s useful on a supplementary level but should never be the determining factor in your decision. Wanting to know if a writer keeps up with what’s going on in the industry is a valid line of questioning; this particular question just doesn’t tell you anything. The fact that I don’t belong to any professional organizations doesn’t mean I don’t take my profession seriously. It means that I’m kind of an introvert and that I keep up with the latest developments online. As I stated with the question about reading other blogs — if you want to know how the writer keeps up with developments, ask that.

Which style guide do you prefer to go by?

This question is only useful if you’ve got two stellar candidates and are splitting hairs to choose one. Or if you have absolutely no tolerance for any style deviations. Sure, of course it’s more convenient and less of a hassle if a writer is familiar with the style guide you use. But that doesn’t mean their writing is any good.

Why do you want to work on this project?

OK, this may be a valid question if you work for a nonprofit and need to hire someone with passion for the cause. But realize that the best freelancers are business people. They take projects where they can add value and that work out economically for both the freelancer and the client. If you wouldn’t demand that an accountant be a cheerleader for your industry or cause, don’t expect a freelancer to, either.

Give me an example of how you’ve incorporated feedback on one assignment into your future work.

The intentions here are good: It’s critically important to know how a writer handles revisions. The last thing you want is a freelancer who gets defensive when you request changes. But the part about incorporating it into future work is irrelevant. A lot of feedback is project- or client-specific. Besides, even in the case where you hire someone on retainer, it’s not a big mystery. The client tells you to do something differently, and you do it. It’s the attitude that matters, not the how.

What is your specialty?

This one is a pet peeve of mine. I completely disagree that writers should choose an industry or topic in which to specialize. I specialize in writing. I specialize in helping clients figure out what you want your audience to think/feel/do after reading a piece of content, and then making that happen. Industry experience can speed things up, of course, but it won’t make up for not knowing how to write. If you’re concerned about a lack of industry experience, ask something like, “How do you get up to speed on a new industry?”.

What’s your proofreading process?

Proofreading is extremely important; how you do it isn’t. You want to know that the writer cares. A better question would be, “How do you react when you realize that a published piece has a typo?” (Hint: The response you’re looking for is cringing embarrassment.)

Tell me about your social following.

This may be a relevant question, but only if promoting your content is a logical part of a writer’s job. If you need a ghostwriter, it doesn’t make a lot of sense for the writer to blast it out to all of their network. I do a lot of ghostwriting for tech, for example, but my social media followers would think it was weird if I started promoting random tech content. And any writers in the bunch would know that it’s because I wrote the article. If it’s business-critical for the writer to promote your content under their own name, it’s an extremely important question. Otherwise, it’s just a distraction.


The bottom line is that you — and only you — can set your priorities for a content writer. It doesn’t matter what anybody else thinks the appropriate questions are, myself included. Start by identifying your priorities — what’s most important to you in a freelance writer? Next, think about the qualities that a person who met those priorities would have. The last step is to come up with questions that reveal those qualities. There’s no magic formula. But if you want to hire a writer who can create content that really matters, you have to ask questions that really matter.





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