content marketing strategy

The First Date Strategy for Hiring a Copywriter

firstdatestrategyforhiringacopywriterPicture it. Late 1990s. Single. Urban. Career Girl.

Those were some good times. Living the dream with my $300 Honda Civic that had the worst paint job ever and sounded like a tank. I really felt like I’d “made it” as I got my first paychecks that weren’t earned by the hour checking out groceries.

Let me tell you what wasn’t so hot back in the day. Being on the dating market. Lots of first dates, not a lot of second dates…and way way fewer third dates. If you’ve ever been a single, mid to late 20 something “lady” looking for love, I’m sure you feel me right now.

At the time, my attitude was that dating was a numbers game. You have to go on a lot of first dates if you have a hope in hell of finding someone who is gainfully employed and not a total head case, let alone finding a partner.

In my mind, hiring the perfect person for your business is like going through the process of finding someone to go out on more than a few dates with. Especially when it comes to copywriters.

Working with a copywriter is about so much more than a short-term hire in your business. To summon up some Jerry Maguire, they should “complete you” by helping you make your thoughts make sense and writing words that sound like you, but way better.

Tall order wouldn’t you say?

I know that sounds heavy, but I’m sure you’ve had the experience of hitting up a website and feeling like something was seriously off. Or like the words you are reading sound nothing like the person you know. Even worse, you aren’t sure what the jack they are even talking about as the copy is loaded with big mumbo jumbo nonsense words like transformational life transformations or crap about authentic awareness.

Hello, disconnect.

When you run a business based on your website, disconnected copy can be so painful that it messes with your business, literally.

The bottomline. You need to be picky when it comes to your copywriter. And I can guarantee you, most people are not picky enough.

Think of it this way. Before inviting them home to meet the parents, you want to take the time to have the kind of first date that you run home to tell your BFFs about because it was the best date ever.


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Before you embark on the search for a copywriter, here’s my first date prep strategy to help you make sure that you have the best possible experience:

1. Get Clear on What You Want

Before you even bother going on a date, you need to be clear on what the plan is. Are you dating for kicks or are you looking for something more?

Before you can really work with a copywriter, you need to lock down on what your brand’s messages are. Get crystal clear on your messages, tone/manner and more before you make a plan for your date. A strong copywriter can help pull that out of your head and shape it, but you need to stop yourself from expecting them to be clairvoyant.

After 13 years of marriage, if I can’t read my husband’s mind, your new copywriter likely can’t when it comes to creating your sales page or new opt-in PDF.

Creating a well thought out map of your brand’s messages and determining a content strategy before you hire a copywriter, can save major time and headaches later.

2. Find the Right Fit

When you are looking to hire a copywriter, you will have a wide range of people to pick from.

As a copywriter myself, I guarantee you there’s a lot of us out there. As the saying goes, with something for everyone. Cute, edgy, darling, uber professional…there’s a copywriter for that.

Selecting a perfect-for-you copywriter is about so much more than going based on a recommendation from someone you trust. Your business bestie may have totally different needs or expectations than you do. They may be more sweet and sassy when you are more rock and roll.

References and recommendations are good to a point, but don’t let it be a substitute for doing your own recon first. If you’ve ever been set up on a blind date, you know where I’m heading. References from “your people” can be like relying on a friend to set you up on blind dates all the time, only to finally realize that her only criteria for picking men is that they are single and have a pulse. Dating fail.

Take the time to do your homework by reviewing the writer’s portfolio and asking for samples. You want to ensure their voice is adaptable or a strong fit with your brand.

If your brand is more traditional, hiring a copywriter with a playful writing style who has no experience writing for your audience may result in copy that isn’t a good fit. (Hey, girl hey, copy just isn’t going to work for your law firm, now is it?)

3. Don’t Let Price Woo You 

When a first date includes a really over the top dinner at a swanky restaurant, it’s easy to be wooed into thinking that your date is better than what they really are.

As humans, we are trained to think that high prices equals high quality. With copywriting, like that fancy date, money spent is not always an indicator of quality.

If you’ve ever tried to hire a copywriter you’ll find prices from $99 to $9999. When it comes to pricing, copywriting is the wild west. It’s open season with people being able to charge whatever they want, whether they are worth it or not.

On top of that, anyone can call themselves a copywriter. There’s a big difference between being a “good writer” cranking out papers at college and actually being a writer with training and experience.

Take the time to dig in a bit and see if the price is justified or if that person is straight up delusional:

  • How long have they been writing as a professional?
  • What training do they have?
  • Are they keeping up with the latest trends and best practices?
  • What companies have they worked with?
  • Do they understand how to create copy that converts and actually sells?
  • What client results or testimonials do they have to articulate the value of investing with them?

4. Understand the Possibilities for a Potential Relationship

When I was on the dating circuit, I had a list. And yeah, I know you had one too, so don’t even pretend you didn’t. My list was focused on my deal breakers, things that simply weren’t going to work for me. (Hint: Having a bus pass and not a car was near the top.)

With your new partner the copywriter, you want to make sure that you are clear on how you can work together. Before you go any further, you want to see if your list matches with what they can offer and how they work.

Ask questions about the process so you have a picture of what to expect with timelines, touch points, delivering feedback, revisions to drafts and more.

Opening up that line of communication in advance helps you get a feel for if their process will work with you and your business and if there’s any hope you’ll make it to date two, three or beyond.

Get Picky. Your Business will Thank You.

Be picky when it comes to your copy and who you hand it over to. Before you dive into your first date, take the time to do a little recon in advance so you can decide if you want to even go there. Your business will thank you.

If you want to check out more on hiring a copywriter, you can check out this video.

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