The Art of Questioning

I’m naturally curious. It’s what led me to become a news reporter – a career choice that was no surprise to my family. I chuckle about the 1970s cassette recorder my brother recently uncovered in the attic. It still worked as we rediscovered that scratchy audio of 7-year-old me conducting interviews with my fake British accent (who knows why). I was also probably holding my hot pink hairbrush as a microphone.

As a kid, I learned the value of an open-ended question and continued to appreciate as a broadcast journalist that not all questions are created equal. Or how we ask them.

My interviewing style developed as a form of exploration rather than interrogation. The tone, the sequencing, patience with the pause, and follow-up questions. A genuine interest in learning about not just a story but the people behind it.

Easing into my radio interviews I could often find an unforced connection with the person on the other end of the microphone. There was great satisfaction in creating a comfortable setting where they could relax, layering facts with personal details, insights, and feelings. 

A respected colleague preferred his hard-hitting interview style. He took pride in his efficient reporting of his story – the “who, what, when, and where” method while I reached a little deeper into the “how” and “why”. His stories were accurate and on point. My stories weaved together the facts with the human experience. We both performed our jobs well, in our own chosen style. He went on to become a financial advisor. I transitioned to a communications director.

Why Asking Great Questions Matters – Whatever Your Job May Be.

My transition to public affairs roles felt natural. I was at home in the rough and tumble world of politics where I crafted behind-the-scenes persuasive strategies and public storytelling to help pass landmark public policy. Days were filled with questions on high-profile issues – seeking to understand a vision, create a public affairs strategy, or resolve a controversial issue. It wasn’t merely about the facts but unwrapping why an issue or project matters and for whom.

Fast forward to today, and I still feel the gravitational pull of powerful questioning. This time as a communications consultant. Asking questions to learn. To problem solve. To break down barriers and discover opportunities. Creating communication and change-management strategies to make a meaningful difference.

I’ve observed that in high-pressure workplaces and team environments, the drive to be efficient and productive can make us hesitate to ask – or receive – questions that might slow us down. The reality is that asking questions helps an organization achieve its goals, make better decisions, and build stronger relationships. This short-term investment pays dividends with enduring results.

Asking Questions Demonstrates Empathy

When empathetic people ask questions, they unlock inhibitions and create safe places for others to share thoughts and ideas. And when you’re fortunate to connect on a deeper level, you can learn what prompts fear or brings people joy. 

This is part of making work more human. Taking time, growing trust, and creating bonds within teams.

Create the Time and Space – and Go Where the Conversation Leads You.

Tell Me More

A question doesn’t need to be a fast, straight road to a single destination. Ask the follow-up question. And another. Encourage continued sharing. “Tell me more” is one of my favorite invitations – both on a conversation's giving and receiving side.

Pause

Don’t overlook the power of the pause. It isn’t necessarily an end to the answer or a signal to change the subject. Silence is powerful in communication. Become comfortable with it. There are wonderful times after what may feel like an awkward silence when magic follows. 

Breathing Space

Embrace the pause as natural breathing space. “Uninterrupted listening” is a skill I’m learning to improve in my work with A Human Workplace. The more I practice it, the easier and more rewarding it becomes.

The Sigh

Explore the sigh. You’ve been there, someone answers a question one way with their words, yet another way with their sigh or slumped shoulders. Put those words aside for a moment and gently follow up on the emotion expressed. There’s something there for them to release.

What Else?

If the conversation seems to stall, consider asking “What else is on your mind?” Or posing this question: “What do you wish I’d ask that I haven’t?” Some of my most surprising news stories resulted from this one closing question. As did some of my most creative communications strategies.

You Can Learn to Master the Art of Thoughtful Questioning. 

Perhaps this is where you’re hoping for a Top 10 List of Mastering the Art of the Question. I can’t pretend that there’s a one-size-fits-all formula. But I will offer this: exercise that curiosity muscle. Be genuinely inquisitive and an active listener. Care to prepare. Before you’re in the conversation, think in advance of a thoughtful opening question or two, and be open to where the road of answers (and pauses) leads you. Listen to others who ask intriguing questions and take notes. Even in this age of technology with my array of digital devices, I still love colorful Sharpies and bright notecards to post insightful questions on my old-school vision board.

And finally, this. Remember that conversations take at least two people – an exchange between giving and receiving. As you increasingly appreciate the art of a thoughtful question, actively engage on the other side of it as well. And help cultivate a team environment that warmly welcomes questions as vital to its collective success.