What's Really Possible Blog

A Person of Questionable Character

Written by Jill Konrath | Nov 11, 2026, 3:00:00 PM

Doesn’t sound like a compliment, does it? But I think it might be one of the best things someone could say about you. Think I’m crazy?

I’m not talking about simple yes/no questions. Nor am I talking about questions that are a setup to make you look stupid, like, “What idiot would think that?”

Instead, I’m focused on the wonderful questions that engage your mind, push you to think beyond, and open the door to new possibilities.

Remember, in my last newsletter, I asked you, “What are you most proud of?” Keep thinking about it! We’ll come back to that question soon.

My obsession with questions began in high school. According to Seventeen magazine, the key to dating success was a girl’s ability to get the guy talking about himself.

That meant she needed to ask good questions. Back then, I even wrote the questions down before I went out on a date and stuck them in my purse. (Nerdy, I know.)

When I started teaching, I discovered that certain types of questions truly engaged my students. They weren’t the ones that asked for a yes/no answer. Instead, students had to think, analyze, or extrapolate. Hmmm.

Then I went into sales and discovered the significant impact asking the right questions can have on a meeting with a potential client.

Note: If you sell, download my first book: Winning Sales Questions. It’s free! And it’s filled with “550 Powerful Questions to Engage, Motivate & Differentiate.”

Personally, I use questions to help me see the options in my life. I’m still asking myself, “What do I want to be when I grow up?” or “What’s next?”

Sometimes my ideas seem audacious. If I ask myself, “Can I really do that?” it’s easy to answer myself, “No!!! You’ve got to be out of your mind!”

So instead, I ask questions like: “How can I make that happen? Where can I learn more? Who might have some insights for me?”

That opens my brain up to all sorts of possibilities. I notice ideas from others. I find resources. And, slowly, a plan emerges. What once seemed impossible is now within my reach.

My newest book, Pivotal Moments: The Springboard to New Possibilities, focuses on questions you can ask yourself when you’re trying to figure out: “What’s next?”

It’ll help you clarify what you want, uncover hidden possibilities, reduce your fear, build momentum, and take the next right step.

Because I truly believe that so much more is possible if we just ask the right questions.

Questions are the answer!