7 Odd, But Essential, Questions to Ask Your Next Writer

29th, 2015
Keyhole - Content Marketing - Joe Dudeck
Joe Dudeck
President + Founder
29th, 2015
Keyhole - Content Marketing - Joe Dudeck
Joe Dudeck
President + Founder

A great writer’s like a great pair of shoes.

Think about the shoes in your closet right now. You’ve got some you pull out and use nearly every day—maybe you’re wearing them right now. They work well for you. They know you. They may or may not be the most stylish, but you know what you’re going to get in the end—a comfortable experience.

And then you have some shoes buried in the back of your closet that you’ve long since forgotten. The shoes you bought online that one time just because they looked so damn good…until you tried them on and realized they’d never work for you.

For me, it takes months to buy a new pair of shoes. I start researching online. What do I need? What’s out there? What are the current styles? What styles will last? And then I start pinpointing local stores that match those styles. I can’t buy online. I need to go and touch the shoe. Feel how it moves. Try it on and walk around in it for 20 minutes. Only then will I know when I’ve found the right pair for me.

It’s a meticulous process, but it works. My shoes give me no problems and tend to last 2-3 years.

To find a great writer, I believe you have to do the same. You need a writer who knows you…not just someone who can string words together in a sentence. You need a person who you can connect with and who you trust. A writer who can take your ideas and mold them into compelling messages for your audience.

And you’re not going to find that person by simply looking at writing samples or by checking past work experience or by making sure you agree with their compensation package.

To find the best writer…your best writer…you need to know the person. You need to spend time together. Go out for coffee and ask him/her some questions. Not interview questions, but real questions.

Here are seven questions I suggest asking your next writer:

  1. Who was the main character in the last novel you read and what about that person most intrigued you?
  2. When you last took someone to lunch, can you describe in detail the scene around you?
  3. Can you tell me about a time when you were overcome by emotion?
  4. What’s one childhood memory you hope to never forget and one adult memory you wish you never had?
  5. If you gave your own eulogy, what’s the greatest achievement you’d share?
  6. At that same funeral, what words would someone put on your tombstone?
  7. What’s your why in life? What’s your purpose for getting up each day?

There are no right or wrong answers. But each one should give you a greater glimpse into the people you meet. You’ll discover things like how they pay attention to detail, understand elements of storytelling, feel about vulnerability, cherish events, overcome challenges, see themselves, believes others see them, and look at the value they add.

Go on, give it a try the next time you need a writer. But be prepared…you may be asked some of these same questions in return.

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