[Tipster] The First Question Isn’t the Best Question

tipster post Jul 28, 2023

Coach Eddie, my 7th-grade softball coach, is the reason I’m good at asking questions.

The spring season wrapped up, and my 16-month-older sister and I biked over with my dad to Coach Eddie’s house to pick up our participation trophy (because you can be certain that the Mighty Mustangs didn’t get a trophy for placing).

I’m not sure what Coach Eddie said to us. But legend goes he asked me and my sister a couple questions, which we answered in a way that infuriated my father.

Our ride home, my father zoomed ahead of us, yelling over his shoulder: “Why couldn’t you look him in the eye when you spoke? Why couldn’t you answer in more than one-word sentences?”

As I retell this story, I realize this moment was a fulmination of frustration with his daughters’ shyness.

When we got home, my parents retreated to their bedroom to discuss what they should do about Melissa and Kresta’s social awkwardness.

Their solution felt draconian.

“Melissa and Kresta, we’ve decided that every day for the next week, you need to seek out one adult and ask them three questions.”

I recall peeking over our backyard brick wall and asking a friend if her mom could come out and talk. “I need to ask her three questions.”

The 3-Question Lesson

Today, my sister and I are great conversationalists. Put us in a room with a stranger, and by the end of the night, their guts will be spilled. My parents think their parenting was brilliant.

Even if I question their extreme measures on occasion, the 3-Question Lesson taught me how to ask good questions. More importantly, it taught me how to ask good follow-up questions.

Because the first question is never the best. It takes at least two follow-up questions to strike at the core.

Think about how a conversation might have gone with my friend’s mom:

Me: “How was your day?”

Friend’s Mom: “Good.”

Me: “What made your day good?”

Friend’s Mom: “I finally slept well last night. I felt rested all day.”

Me: “Why haven’t you been sleeping well?”

Friend’s Mom: “I’ve been worried about a lot of things.”

Me: “What have you been worried about?”

Friend’s Mom: “My mom isn’t doing well…” 

Three questions always lead to more questions: the best questions. And that demands curiosity.

The Foundation of Good Writing Starts with Curiosity

Asking good questions is the foundation of writing a readable book.

The most basic question you ask when you begin the journey to write a book is: “What is my book about?”

The obvious follow-up question is, “What books have been written on this topic?”

The follow-up question to the follow-up question is this: “What does their book not offer that I can offer in my book?”

I imagine there would be at least another 50 follow-up questions to that one, after you start digging into the competitive research.

Ultimately, you’ll question your way to the follow-up question of follow-up questions: “Why should I write this book now?”

You have to answer those questions.

Authors who don’t? They lack humility. Their hubris curtails curiosity.

But you must maintain curiosity throughout the duration of the book writing process.

  • Be curious when you interview people on your topic. Have a set of questions, but be prepared to go off script if your curiosity tells you to ask about the thing your interviewee cut off talking about. There’s likely a story buried in their hesitation.
  • Be curious about the research already done on the topic. Don’t just read the first article on the topic, but dig for the original source that the article is based on.
  • Be curious when you read something that makes you think, “Why would anybody think that?” Ask at least three follow-up questions to understand their position.
  • Be curious enough to push through confirmation bias. Ask questions that might derail your thinking.

You get the idea. Ask the first question. But always ask the follow-up question. Your reader will thank you for digging in.

Now buckle up and write.

Melissa Parks



Email: [email protected]