The Question That Makes People Remember You

You'll want these handy as we go through today's edition:

I remember sitting next to a director from another company at an industry event. She was someone I'd wanted to meet for a while.

I had my whole conversation ready. What I'd been working on, what I'd achieved, anything that might make a strong first impression.

Before I could get into any of it, she mentioned something she was struggling with. Her team had just had priorities shifted on them without warning, and now buy-in was low and goals were unclear.

I almost jumped in with how I'd handled something similar. I very nearly made it about me. But something stopped me.

Instead, I asked: "What's making the buy-in part so challenging?"

She paused, looked at me, then talked for ten minutes straight. Competing stakeholders, conflicting metrics, pressure from the MD. I barely said a word. I just listened, asked two more questions, and let her think aloud.

At the end, she said: "This has been really helpful. Let's schedule time to talk more."

I never mentioned my accomplishments. Not once. But two weeks later, she called and asked if I'd be open to consulting on a strategic project.

Not because of what I said about myself. Because of what I asked about her problem.

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When you ask a great question, it does two things at once. It helps you collect information and builds trust at the same time.

The simple act of asking more questions, especially follow-up ones, makes people like you more and leaves a lasting positive impression. Rather than trying to work a room, introverts often do their best networking by going deep with one person at a time.

Curiosity is strategic. It leads to better decisions and more meaningful progress. When you talk about yourself, you're asking someone to care about your experience. When you ask about them, you're showing you already care about theirs. That difference is everything.

Asking good questions is as much art as science. It builds both trust and psychological safety in ways that talking rarely does. Introverts are more likely to ask insightful questions, identify overlooked risks, and engage more deeply in conversation than their extroverted counterparts.

This is your advantage. You're already wired to listen carefully, prefer depth over small talk, and notice what others miss. Asking strategic questions uses all of that without requiring you to self-promote or dominate the room.

After that conversation with the director, I started paying attention to which questions created a connection and which ones fell flat. Three patterns kept showing up.

People are culturally wired to ask surface questions. "How's the project going?" "What are you working on?" Try going one level deeper. "What's the hardest part of that project right now?" "What would make that easier?"

Prompting for more in an open, inviting tone helps people share what's beneath the facts. Introverts have a natural edge here. That calm, grounded energy and steady presence often makes the difference when paired with a question that actually goes somewhere.

This is the most powerful one. After someone answers your first question, ask a second one based on what they just said. "You mentioned the timeline feels tight, what's driving that urgency?" "You said the stakeholders are misaligned, where's the biggest gap?"

When you ask follow-up questions, you signal genuine interest, and that kind of attention is deeply flattering. It gives the other person space to go deeper. That's exactly where trust starts to form.

Sometimes the most valuable question isn't about the problem at all. It's about how the person is thinking about it. "What would this look like if it were easy?" "If you could change one thing about this situation, what would it be?" "What are you optimising for here?"

Thoughtful questions encourage reflection on new possibilities while reinforcing clarity and alignment. When you help someone think more clearly, you become someone they want to think with again.

Use these before any conversation where you want to leave a stronger impression than usual. A networking chat, a coffee catch-up, or a meeting where you'd normally default to talking about yourself.

Here's the ChatGPT prompt for preparing better questions:

For building your follow-up habit:

"Here's what someone said to me in a recent conversation: [paste what they said]. Give me three follow-up questions I could ask that show I was listening and help them go one level deeper."

This turns your natural tendency to listen and observe into an influence strategy that actually works.

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I've come to learn that the people with real influence aren't the ones talking. They're the ones asking the questions everyone else wishes they'd thought of. The ones who make you feel heard. Who help you think more clearly.

This plays directly to how you're already wired. You listen deeply. You think before you speak. Use that. Turn it into questions that make people stop and think, rather than just nod and move on.

One great question does more for your influence than twenty minutes of talking about yourself. Because the question is about them. And when you make someone feel understood, they remember you. Not as loud. As curious. As caring.

Thank you for reading, and for being part of a community where we build influence through depth, not volume.

In your corner,
— Steven

P.S. If this resonated, forward it to an introvert who's been told they need to "put themselves out there" more. There's another way.

P.P.S. Want to put today's ideas into practice straight away? The FREE Networking Scripts for Introverts gives you the exact words to start deeper conversations, without the small talk, the performance, or the energy drain.