Four simple techniques to build trust, spark stories, and connect—on your podcast and in everyday life.
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As a podcaster, you’re often walking into conversations with people you don’t know well — or at all. Maybe they’re a rising entrepreneur, a best-selling author, or someone with an amazing life story. But unless you already have a deep personal connection, you’re starting from zero. That’s where the art of asking the right questions becomes critical.
The right questions can open doors, spark stories, and build instant rapport. The wrong ones? They can shut things down, put your guest on the defensive, and kill the vibe of the episode before it even gets going.
And here’s the thing: this isn’t just about podcasting.
Whether you’re meeting someone at a networking event, catching up with a coworker, or connecting with a friend who’s going through something big — asking better questions changes everything. It deepens conversations, builds trust, and strengthens relationships in every area of life.
Here are four simple but powerful ways to ask better questions — from my book Good Listen – that invite trust, connection, and memorable dialogue.
First impressions matter. So whether you’re turning on a mic or just walking into a room, lead with questions that feel welcoming and affirming. Avoid anything that might seem judgmental or too probing right away.
Instead of “Why didn’t that work out?” try “What’s something from that experience you’re proud of?” This immediately puts the other person in a mindset where they can reflect without feeling defensive.
When people feel safe, they share more. And whether it’s your guest, your co-worker, or your third cousin, that’s the beginning of meaningful connection.
Yes or no questions stop conversations. Open-ended questions open people up.
Instead of asking, “Did you enjoy that project?” try, “What part of that project challenged or excited you the most?” This invites reflection and storytelling, whether it’s during a podcast or over coffee with a friend.
People don’t usually reveal much when you ask only for facts. But ask them for a story, a turning point, or a memory — and you’ll start seeing who they really are.
This works wonders in everyday life too. Want to get past surface-level talk with someone? Stop asking, “How’s work?” and start asking, “What’s been the most interesting thing going on at work lately?” Watch the difference in their response.
This is the human heart of all good conversation: making the other person feel important — not through flattery, but through genuine interest.
In podcasting, this can mean actually listening instead of waiting to talk. In daily life, it might mean asking follow-up questions when someone shares something personal instead of changing the subject. It’s about leaning in.
When people feel valued, they open up. They feel safe being more real with you. This is how you move from small talk to substance.
Great conversations have rhythm. Each question should help build trust, move the story forward, and deepen the connection.
Ask things like:
These kinds of questions don’t just work on a podcast — they work around the dinner table, at work, in text threads with friends. They help people reflect, connect dots, and show up more fully.
If you want to be a better podcast host, start asking better questions. But here’s the bonus: these same questions will also make you a better friend, partner, leader, and human being.
Positive, open-ended, story-inviting questions that make people feel seen and spark deeper dialogue — those are the ones that make conversations come alive.
And in a world full of noise, a real conversation stands out — on the mic, and everywhere else.
