Hiring a copywriter doesn’t have to be a daunting task. For many, the process has an unnerving aspect much akin to an interview. The right questions will go a long way.
What you have to keep in mind is that like an interview or a first date, the selection process is a two-way street.

Not only do you need to ask the right questions, but you also need to answer the right questions. It should be a huge red flag if your potential writer doesn’t ask anything of you that has value.
Over-eager candidates aren’t always a bad choice, but you should be careful when going after them. If they easily lower their rates or ask you up front how you can help them (give testimonials, reviews, etc.), you should take pause and consider what the actual goal is.
The primary focus should always be on your needs and projects. While you may need to loosen the purse strings a bit, hiring a copywriter that values your projects and time over their own goals is worth the cost.
Below, I offer you some questions that should make it into your interview with a potential copywriter. These questions aren’t geared towards making sure your project is done; they are designed to make sure you are compatible enough to work on any projects you may have.
The goal, of course, isn’t to just find someone to write what you need doing right now, but someone able to handle any future projects that come up. One well-researched copywriter is worth far more to your time and budget than hiring a new one for each project that comes up.
These questions will help you find that candidate.
What is your track record for meeting deadlines?
This question will almost always be answered with something like “I am prompt and always on time with any deadlines.” The idea here isn’t to get a truthful answer. No one will tell you that the constantly miss deadlines and pay little attention to your time frame.
Instead, This question asserts that you have strict deadlines and they must be met. It puts the writer on notice of what is truly important: time management.
We all know time is money. You need value for the time for which you pay.
Have you done any previous work in my industry?
Most copywriters will have some form of portfolio for you to look at. Those that don’t (ghostwriters, copyeditors under NDA agreements, etc.), will be able to point you to online articles or websites they have worked on.
The true value of this question, though, is in the long answer. For example: even if I haven’t worked in your industry, I am an expert in it. I am not THE expert; YOU are. However, I am an expert in manipulating words, which is why you want to hire me.
I can research what I need, read your previous projects, interview you or your employees and find out everything I need to know to be able to write compelling copy that matches your voice and expectations. Even if I can’t prove I have done work in XYZ industry before, I should be confident that I can.
Be wary of answers that are short or don’t describe the ability to do the needed research for the project at hand. Don’t shy away from a copywriter that hasn’t done work in your industry before. There was a time when you hadn’t either.
Do you have any contacts in {target audience} circles?
Again, we aren’t looking for an exact answer (although there might well be some). Instead, the way the potential writer answers will let you know if the project warrants further investment.
If you have a copywriter that has a foot in certain social circles where your target audience hangs out, it could benefit you. Allowing them to claim the work, for example, will have the writer talking about it to potential customers, who will end up on your site to read the boasted works.
Likewise, allowing the copywriter to claim their work is generally less expensive than having them ghostwrite. Ghostwriters get to charge more because they don’t get credit and the fall back that comes with it (visits to their site from yours, links, a bio, exposure, etc.)
Weighing the pros and cons are, of course, up to you. However, asking this question will put you on the right path to that final decision.
Are you comfortable with other deliverables such as images or infographics?
Even if you don’t plan to have infographics or other materials made for the piece, it is always good to know if your potential new copywriter has the capability to provide them.

You should make it clear if the project being interviewed for needs them or not. However, you might have future projects that do and knowing if your new copywriter can handle them is a bonus.
While this question isn’t considered “crucial” as you are hiring a copywriter for words and expertise, it is still good to find out. It is a point-based question that could prove the final factor when deciding between two final candidates.
Are you talking to other potential professionals about similar projects?
This is an important question that doesn’t get asked enough. It isn’t straight-forward as asking the writer if he has time to take on your project. However, it serves the same purpose.
If the answer is that they are not, or you glean that he or she has the time to devote to you and your needs, you have it in writing (or on a phone call) and can then hold them accountable for it.
In most situations you won’t know about other clients the writer has, nor should you. However, if they have trouble with your deadlines and it comes up later that they are working too many jobs, it is almost too late to pull out.
We are all in this for the money
Writers want to make money and develop long-term contacts.
The interview phase should be less nerve-wracking and more pleasurable. Getting both of you on the same page is a must. Asking the right questions will always help you make sure the potential writer and your tastes line up.
If done correctly, the bond can last for years, making both of you quite happy.
If you need a project completed and would like to ask me these questions, feel free to send me a note.