Hi Reader – how are you doing today?
I mean that as an actual question, not just a way to start an email. Which, as it turns out, is more or less the whole subject of this week’s note.
Earlier this week, I spent 90 minutes on the asking side of the microphone.
I was hosting a podcast conversation (hello, Headline podcast, my pride and joy), and I’d done what I always do: prepared. A full page of questions, ordered, sharpened, the good ones highlighted with my yellow highlighter pen. I like to walk in ready. It is, if I’m honest, a habit left over from twenty years of rooms where being ready was how you earned the right to be there.
And then, about twenty minutes in, our guest said something that didn’t fit anywhere on my page. A small thing, almost an aside. I felt the pull to nod, tuck it away, and steer back to question four.
Instead, I put the page down and asked him about the aside.
What followed was the only part of the conversation I’ll actually remember. He answered a question I hadn’t planned, I asked another I hadn’t planned, and somewhere in there, the conversation stopped being an interview and became the real thing. Afterward, he wrote to say the questions were thought-provoking. But I hadn’t been clever. I’d finally just stopped preparing and started listening to him.
Here’s what caught me as I left the studio.
For most of my career, I believed my job was to have the answers. Walk in with the plan, the number, the take. It is a genuinely useful skill, and it is also a quiet trap, because the person with the fastest answer and the person who asks the question that opens the room are almost never the same person.
And you’ve probably seen this too – we reward the answer. We rarely notice the question that made the answer possible.
This is where I go to the research (you know I love a good reference).
There’s a study from a Harvard team (Yeomans, Brooks, and colleagues) with the almost-too-perfect title “It Helps to Ask.” Across conversations between strangers and even a field study of speed-daters, the people who asked more questions (and especially follow-up questions), the kind that prove you were listening to the last answer rather than waiting to deliver your own, were consistently better liked and more trusted. Not the people with the most polished thing to say. The people who were most clearly paying attention. Asking is not the weak move we’re afraid it is. It’s the thing that draws people toward you.
And listening does something to the person answering, too. A 2024 meta-analysis (by Avraham Kluger, Herman Aguinis, Guy Itzchakov and colleagues) pulling together more than 600 findings across 400,000 people found that feeling genuinely listened to is tied more strongly to the quality of the relationship than to almost anything else.
And the same researchers have shown something subtler still: high-quality listening doesn’t only make the speaker feel good, it sharpens their own thinking with clearer attitudes, less defensiveness, contradictions they’d been talking over suddenly visible. Being listened to well doesn’t just change how the speaker feels about you. It changes what the speaker can see. My questions weren’t the gift in that recording. My attention was.
It mirrors what I keep finding with coaching. The steady pull, every single session, to hand someone the answer they came in for. And the harder, better move almost every time: to ask the one question they haven’t asked themselves, and then to be quiet long enough for their own answer to arrive. The answer was never mine to give. The question was the whole job.
It’s a good part of why I wrote Clarity in Chaos: Lead with Purpose in Disruptive Times. When everything is loud, the instinct is to lead with louder answers. Usually, the thing that actually cuts through the noise is a better question, asked of the right person, followed by the discipline to listen to the answer.
So here are two ways to try it this week:
Option A: Ask the one question and sit in the silence. In one conversation this week, ask the question you’d normally skip past. The real one, the follow-up, the “say more about that.” Then stay quiet. Don’t fill the pause with your own answer. Don’t move to question four. Just let it sit long enough for the real thing to surface. That silence is not you failing to lead. It’s the listening doing its work.
Option B: Trade one instruction for one question. If you lead anyone, take a single moment this week where you’d normally tell them what to do, and instead ask them what they see, or what they’d do next. You’ll lose ninety seconds of efficiency. You’ll find out whether they’re following your plan or actually thinking, and you’ll hand them a little more ownership than they had this morning.
Me? I’m taking Option A. There’s a standing conversation I always walk into with a page of answers, because answers feel like proof I’m doing my job. Next time I’m bringing one real question and my full attention, and leaving the page in my bag.
So, which one is yours this week?
– Megan
