The Art of Asking
How the Right Questions Turn Moments Into Movements
Hey, I’m Penny Terry and I love writing about ‘soft skills’ while simultaneously hating the phrase ‘soft skills.’ At the moment I’m writing a 10-part series about hosting everything from meetings to podcasts, to events. Even if that doesn’t feel like your thing, I reckon you’ll get more out of it than you expect. We all host something, most days. Either way, we’ll return to regular programming once the series is done.
A few years back, I found myself sitting in Canberra airport, a glass of sparkling wine in hand (it was meant to be coffee, but the moment called for bubbles), waiting for my flight home after hosting a keynote. Yep, I say hosting, not giving—because somewhere along the way, I realised I can’t help but pull people into the conversation—I blame the many years of hosting talkback radio. What starts as a story usually ends with me chatting with the audience, interviewing people on the spot, and weaving their words into the talk. So my keynotes become this blend—part storytelling, part spontaneous interview, and a good dash of “let’s see what happens next.” It’s not the traditional approach, but it’s how I find my connection with the room.
That day, the room was buzzing. People seemed engaged, and I walked off stage feeling like I’d done my job.
But as I sat in the quiet of the airport lounge, emails started pinging in. Someone from the audience was thanking me for the session and linking me to someone they thought I should meet. Another was sharing what had stuck with them, and on social media, I was being tagged in photos of people wearing clothes that made them feel confident—which is something I mentioned during the talk.
As I sat there in the quiet of the airport lounge, I felt more connected to those audience members than I had when we were all together in the room. It was as if the real conversation had only just begun.
Yes, the energy in the room had been quite electric, but the true power was starting to happen, in this otherwise quiet moment. During the keynote, people were mostly absorbing, but now they were engaging and expanding on the conversation. I began to realise that it wasn’t the keynote itself sparking the connection—it was the simple, spontaneous questions I asked at the end. Those questions, more than anything, gave people space to take what we’d started and let it grow beyond the room.
Before I left the stage, I asked some things that I hadn’t always been so intentional about. I asked the audience to connect with me on email, and to share what they were thinking about. I even asked them to share something on social media and tag me—I did this explicitly (which still makes me cringe), and yet I was surprised when they did. Plus, I asked them to link me up with someone else they thought I should chat to… and again, they did! I then followed up with the people I’d interviewed during the session, asking, "Are you ok if I share your story past this room?"
And sitting there in the airport, I realised those simple questions had sparked something bigger.
The value of a conversation isn’t just in what happens during the event, or podcast or meeting, it’s in the ripples that come after.
But they only start if you throw out a few stones.
The Three Key Questions to Ask
Whether you’re hosting a podcast, a keynote, or even just a small meeting, I reckon there are three key questions that are useful to ask—of guests, the audience, the participants:
Permission to Share – Just because someone shares their story in the moment doesn’t mean they’re comfortable with it being broadcast more widely. Always follow up with, “Can I share this in a blog, podcast, or on social media?” It’s about respecting their voice and giving them ownership over their story. Plus, it validates their contribution——it’s evidence that you value it and think it deserves to be shared.
Promotion and Referrals – Your guest or audience members can become your biggest advocates if… you simply ask. While you’ll cringe at first, find your way to say “What, from this, could you share with your network and they’d really appreciate you for it?” Plus, often your next great guest or idea comes from a referral or recommendation so don’t forget to ask, “Who else should I be speaking to? Where else should I go?” People often just need a gentle nudge to help spread your message.
Connection and Feedback – Ask your audience or guests to connect with you personally, and invite them to share their thoughts. You might say, “I’d love to stay connected—and find out what stood out to you today?” or “What didn’t I talk about today that I could have - what would you have added?” As author Michael Bungay-Stanier will attest too, people love to give advice - it’s usually just a matter of giving them the opportunity. However, I’ve found it’s important to think about the way you frame this question so you get feedback and connections that serve you.
There are so many different ways to ask these questions, well. These days I ask them quite differently than I did that day in Canberra, but the outcome is the same—they extend the life of the moment and transform it into something lasting. Our audience isn’t passive; they can become part of the ongoing story.
So, go throw some stones.
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Of course, the questions don’t stop there. After every event, we need to ask ourselves and our teams some critical questions too. That’s where real growth happens. But more on that next week.
LAST CALL: Hour of Power Tickets
I’ve you’ve been thinking about it—now is the time to click that button 👇
The first session is this coming Monday lunchtime, followed by two more sessions over the next two weeks.
Ask Better Questions – Be Curious (Monday, September 9th, 12:30–1:30 pm)
I’ll take you through my Question Compass, it’s a guide to help ask insightful questions that uncover what’s often missed. Great for anyone who facilitates, interviews or just wants to get better insights from their people or clients.Tell Better Stories – Be Concrete (Monday, September 16th, 12:30–1:30 pm)
We’ll dive into my storytelling structure and explore four ways to find and then craft compelling stories. Great for anyone who wants to be more engaging or presents publicly in any way, from the stage to the media to workshops.Have Better Conversations – Be Influential (Monday, September 23rd, 12:30–1:30 pm)
This brings the top two together and explores my nine-step framework that helps us guide conversations in an influential way. Great for anyone who wants to move people from one perspective to another.
They’ll be fast and fun. Hope to see you there. Here’s that button again.