I love asking questions. The inquisitive part of me adores learning and having meaningful conversations that go beyond surface-skimming chit chat. As a business owner, I’ve learned that asking questions is a crucial component of building a brand and making connections. But there’s an art to it. Knowing the difference between “okay” questions and “great” questions is like going from Kansas to Oz.

For example, “What do you do?” is an okay question. We ask and answer it all the time. But how often does it lead to thought-provoking conversation? We give our pat answer, reciprocate the same question and move on.

There’s got to be a better way.

So I went to an expert on questions (yes, there is such a thing), my client Aileen Gibb, author of Asking Great Questions.

Aileen Gibb with her latest book “Asking Great Questions”.

What’s the big deal about questions?

“The most powerful conversations happen when you ask questions” Aileen explains. Good questions and meaningful answers can change the world.

Mind. Blown.

What is the best question to ask?

When you enter a conversation with “preloaded” questions, you can’t help but mentally tick off the boxes in your head. Yes. Yes. No. Yes. You’ve gone from “whoa” to “meh” in four questions flat.

“The scary question is the one that makes the difference,” she notes. It’s the one that comes up when you are focusing on the moment, when you are in a back and forth conversational groove. If it makes people pause before answering, it’s a great question.

What is a good question to start a conversation?

“Anything but ‘So, what do you do?’” laughs Aileen. It’s important to be genuinely curious about others. Ask questions you haven’t asked before and you’ll receive interesting answers. Be bold and ask questions that come from a different place than everyone else’s. “What inspires you?” or “What’s a dream or ambition you haven’t yet fulfilled?” gives a conversation a set of sturdy legs to stand on.

Ask open-ended questions such as, “What do you think about…?” It shows a respect for opinions, which leads to trust and understanding.

Why do some business owners and leaders have a hard time asking questions?

As business owners we often feel responsible for having all the answers. We are expected to be decisive, fearless and innovative… and to know the answer before the question has even entered anyone else’s brain space. It’s not easy to hang out in that vulnerable space where we are waiting for answers instead of providing them.

If the floor is open for answers to emerge through asking questions, the possibility of innovation and creativity will be infinitely larger. Our co-workers and clients will feel valued when they realize their voices are important. By letting go of the need to have all the answers and fix all the things, we create an environment of trust.

Asking questions is not a sign of weakness. Rather, it’s a way to open doors and build relationships. Dale Carnegie, author of How to Win Friends and Influence People, once wrote, “Effective leaders ask questions instead of giving orders.”

How can we be better listeners?

“It’s all about the intention you take into the conversation,” says Aileen. Are you truly open to what others say? Or are you attached to specific answers that swing the conversation back to you? Create space for possibilities and surprises. Learn to be comfortable with silence as you wait for a response. Don’t interrupt.  

Trust that the conversation will be way more meaningful than anything you try to force.

People love talking about themselves. It douses our brain with dopamine, a “feel  good” hormone. When you want to make another person feel good, give them space to talk about themselves. Asking better questions is a surefire way to develop lasting relationships and build trust with people. (And that’s always good for business.)

What are your favorite questions to ask? Have you ever been asked a question that stopped you in your tracks?