Hiring a freelance writer can be risky business. Especially if you’ve not hired one before. Of course, you will want to take a look at samples of their work to determine if the writer can construct a coherent narrative. If you are bored half-way through the article, that’s not a good sign. Even if it’s not a topic you are interested in, the writer should at least be able to hold your attention.
Their writing should draw you into the subject.
Once you’ve settled on a few potential freelance writers, you will want to have a conversation with them. When you are interviewing a freelance writer, there are a few not so obvious, but critical questions you want to ask them.
1. How do you hone your craft?
Every good writer is always striving to be an even better writer. You rarely hear a great writer say they have no room for improvement. I’ve listened to countless interviews with Pulitzer-prize winning or best-selling writers, and they all say they strive to improve with every piece they write.
Many writers have imposter syndrome. We live in fear that one day, someone will expose us as a fraud. Those suffering from imposter syndrome are some of the greatest writers and journalists out there. They are successful despite their insecurity (or perhaps because of it) because they push themselves to improve with every word they put on paper.
Aside from reading countless books on the craft of writing, every good writer will tell you they hone their craft by writing every day, and by reading every day. It doesn’t matter if I don’t have paid work to focus on today. You can be sure I will be writing. I will also be devouring work of “longform” journalists and writers that I admire.
2. Do you have a contract?
There are two reasons you want to ask this question. The first is to determine if they treat their craft seriously. The last thing you want is to engage with a flighty writer. Any good business person will wish to work under a contract. If the freelance writer you are talking to is vague about terms, they are likely going to be vague about deadlines and expectations as well.
The second reason you want to ask this question is that you want to establish expectations. When a freelance writer gives you a price on a project, it must include rights to the work created (do you require work for hire in which you retain all the rights, or is first publishing rights good enough) and number of revisions. A good contract will protect you and the writer.
Your freelancer should state in writing that the work they create for you will be free of plagiarism*. You would think this would be a given, but you’d be surprised. Every contract should have a clause that covers this.
A specified number of revisions are standard in a contract. A revision clause is not so the writer can pass on shoddy, incomplete work all in the name of “you’ve reached your quota.” It is to protect the writer from the frustration of abrupt changes in the subject matter of the piece.
The bottom line is, you want to work with someone who treats their writing as a business, not a hobby.
*Beware of content farms. Yes, the price is great. You can get a 500-word blog post for $30 or less. I’ve run several pieces of work provided by content farms through Grammarly’s plagiarism check and found them to be filled with violations. Who do you think the offended party is going to go after, a starving writer earning less than minimum wage, or the company who published the piece?
3. Can you work without an editor?
No one is perfect, but your freelance writer should be able to deliver work free of mistakes. You, the client, should be willing to provide an extra pair of eyes for copy editing, but this should not be an onerous task. The truth is, it’s very hard for a writer to catch their own mistakes, because we see what we meant to say, not always what we typed.
When I wrote my book, “The Social Trade Show,” my publisher provided a copy editor (proofreader) and a content editor (flow). Both editors were professionals who excelled at their job. Even with all those sets of eyes, a few mistakes still made their way into the book.
If you are not going to be able to provide any support as far as proofreading and even feedback on the content, let your freelance writer know. I do not expect my clients to provide this service, and I hire my own freelance editor to look over my work for flow and to provide copy editing when needed.
The point is not whether your writer is perfect. Some of the best journalists and writers rely heavily on their editors. The point is that they have resources at their disposal when they need those resources.
4. What is your approach to writing about topics in which you are not an expert?
If you are looking for a freelance writer for technical writing, then you may want to hire someone with expertise in the topic in which they are writing. This is not because someone without expertise cannot do the technical writing, but because it will take them longer to do it well.
For any other type of content, a good writer without expertise in your subject matter will do just fine. There may even be advantages in not having expertise. One is that they may be better at communicating with a general audience.
A writer without expertise cannot be afraid of asking questions or sounding stupid when they are gathering information from your subject matter experts.
When I wrote a piece about thermostatic control valves, I had to go back to the engineer three times before I “got it.” I knew that my lever of understanding going into the project was not much different than that of the audience who would be reading the final piece. I knew there was no way I could write something that was both understandable and entertaining unless I understood the basic concepts.
The trait you are looking for in a freelance writer is the ability to ask questions. That’s what reporting is all about. That’s far more important than a subject matter expert.
That said, if you intend to build a relationship with your freelance writer and are guaranteeing them a good amount of work, the writer should be willing to invest in their education. When I wrote for a robotics magazine, I hung out at a monthly Meetup for roboticist in my area. I also subscribed to IEEE magazine to improve my understanding of robotics.
When I was writing a piece on the intersection of biology and robotics I spent my own time brushing up on Biology 101. What is your potential freelancer willing to do to educate themselves in your area of expertise?
5. How do you deal with deadlines?
Deadlines are so important.
I will never understand writers that do not take their deadlines seriously. Maybe you, the client, are not too concerned if a blog post is a day or two late. However, what if the piece you hired the freelancer to write is for a trade publication? Do you want to risk missing that deadline and losing your opportunity for a great think-piece?
Here’s the catch. Every writer will tell you they take deadlines seriously and meet them. So how do you know for sure? If you are hiring a journalist or someone who’s been published in print or online publications, ask for their editor’s contact information. An editor will be able to tell you if the writer meets deadlines consistently.
If they do not have an editor to contact, consider starting out with a few pieces that do not have deadlines fixed in stone. Create a deadline and ask the writer if they can complete the work on time. Then sit back and see what happens. A good writer will deliver on time or earlier to ensure you have time to make any necessary revisions.
Most writers appreciate deadlines. It’s often the only thing that makes us stop editing. Trust me, we could pick over a piece for months, carefully finding just the right word or turn of phrase. Eventually, we have to say, that’s it, it’s finished. We’ll often not read our work after it’s published because it’s impossible to look at it without finding ways to improve it.
Or maybe not ways improve it, perhaps the phrase I’m looking for is, honing it to perfection. Or wait, that’s too cliche’, what about ways to develop, or sharpen, or augment it. No, augment is not right. What am I really trying to say? Maybe I need to go back to the beginning and consider if any of this is right. Maybe there is a better way to say it all. Maybe I should just start over. Then I hear an authoritative voice in my head saying, “put the pen down and back away from the desk now.”
Photo Credit: By taylorschlades via MorgueFile