Great Questions Are How You Enrich the Quality of Your Life
I'm looking at a beautiful set: a light curtain backdrop with a microphone peering through – the one you may have noticed on the esteemed NPR Music Tiny Desk concerts – two comfy cream chairs facing each other, a white plush carpet, and three cameras ready for their mark.
Even with hours of preparation – listening to multiple interviews, reading articles, and scouring the internet for the smallest details that could positively impact this conversation with Thomas Cumberbatch – I still had butterflies. Why? With the conversations I curate, my hope is for every interview to be meaningful, accurate, and valuable for all parties—my subject, of course, but especially for those who tune in.
As I take a deep breath, close my eyes for a quick prayer, I join my guest for our conversation.
***
I have fond memories of racing home after school to watch interview shows on T.V. While many of these programs were purely for entertainment, there were moments when I was captivated by how a series of meaningful questions could connect two strangers.
I define "great" or “meaningful” questions, as ones that dig beneath the surface, yearn to reveal the truth, and guide us toward understanding why.
“Asking questions is a critical yet underrated skill.”
As the current chief talent strategist and researcher at a celebrity ghostwriting firm and with over six years interviewing 100+ leaders about their purpose, business, and overall outlook on life on the Power of Why podcast, I’ve compiled five practical tips you can use to ensure you’re asking thoughtful questions. Why? Because asking great questions are how you enrich the quality of your life.
Five Things You Can Do Today To Ask Great Questions
(1) Don't skimp on the research.
Even when interviewing someone who already has hundreds of interviews online, devote time to gather data points, scour the internet, immerse yourself in existing interviews they’ve done, read articles they've penned, books they've published, or music they've produced — whatever you can find to help you learn more about their ideas and how they see the world.
Ask yourself, what are people not asking them? What topics have yet to be explored with this individual? Deep research allows you to craft questions with greater nuance and helps you avoid asking questions that have been asked before.
(2) Listen to understand.
Asking thoughtful questions is much more than hearing what people say; it's about grasping the meaning, motivation, or emotion behind their words. My friend, who is also a coach, described this as level 3 listening (empathetic listening), where you pick up on their body language, voice inflections, pauses, and hesitations—all of which enrich your understanding of the conversation.
You've likely heard the saying: to be interesting, be interested. Are you genuinely curious about the person you’re speaking with and the topic you’re discussing? Are you seeking to understand on a deeper level?
(3) Don't fill a moment of silence with nonsense.
Let your conversation breathe. You don't need to rush to fill moments of silence—use them to let a powerful statement hang in the air or give everyone time to think about what was said. But before moving on, ask a follow-up question if there's room to dive deeper (tip #5).
When my brother asked if I equate "nonsense" with humor, I responded “Absolutely not.” Humor is immensely valuable to our existence and essential for how we connect and relate to each other. By 'nonsense,' I meant speaking simply to fill the silence without moving the conversation forward or fostering connection.
(4) Start questions with 'what' and 'how' instead of 'why.'
Coming from someone who loves asking ‘why’ (heck, my podcast is called the Power of Why), I’ve noticed that questions starting with ’why’ can be more challenging to answer. They require deeper cognitive processing and don’t always lend themselves to concise responses.
On the other hand, questions that begin with ‘what’ or ‘how’ typically steer the conversation toward action and detail rather than abstract reasoning.
Don’t take my word for it – try the words on for yourself. Instead of asking, "Why does this matter to you?" ask, "What is it about X that matters to you?"
Here are a few other helpful prompts that you can use:
"Tell me more about…"
"Help me understand…"
"What is it about X that resonates with you?"
"Tell me what you meant when you said…"
"Explain to me how you…"
"Really? Can you say more about that?"
"What do you think/feel about…"
These questions still address the ‘why’ behind your question, but help your conversation partner access their thoughts with greater clarity and focus.
(5) Follow-up.
When I say 'follow up,' I genuinely mean it. Follow up questions hold a special power because they show that you are listening and desire to know more.
You will strike gold when you dare to go beyond the surface of what someone says. Sharing a moment with somebody creates a unique environment and activates particular brain waves that will never be identical to another moment with someone else. This means you have the power to uncover insights or learn something that only you can ask at that moment.
I recently interviewed Susan Odle on the Power of Why podcast, and she talked about the importance of going beyond the surface:
“People tend to focus on the surface of what something is. All the gray stuff beneath the surface will trip you up, making it hard to recover. Do the work early.” - Susan Odle.
Although she discussed this in the context of change management and why more than 70% of all business transformation initiatives fail, the same principle applies to asking questions. By gathering critical information and nuanced details early, you may uncover a more profound story that has the power to change your perspective, and ultimately, your life.
Below are some of my favorite interviews. They illustrate the power of being curious, well-researched, and devoted to going beneath the surface to engage in meaningful conversation:
TLDR
In summary, asking questions is a critical yet underrated skill. If you start here, you will be well-positioned to connect meaningfully with others.
Research who you are speaking to thoroughly
Listen to understand (and be radically present)
Don't fill a moment of silence with nonsense
Start questions with 'what' and 'how' instead of 'why'
Follow up to dig deep beneath the surface
What I saw in those T.V. interviews went far beyond matters of entertainment. It was about humans connecting with another humans. And from their curiosity, came questions that created opportunity for deeper understanding and light.
I'm passionate about this because I've experienced firsthand the transformative power of asking intentional questions. When done well and thoroughly, great questions have the power to open up new worlds for you—worlds of opportunity and wonder.