Interviewing tips that create real connection

In a world full of sound bites and scripted answers, the most memorable interviews are the ones that feel honest, human, and real. Whether you’re hosting a podcast, filming a documentary, or leading a one-on-one conversation, real connection doesn’t just happen—it’s created.

The best interviewers know how to build trust, ask meaningful questions, and hold space for the unexpected. If you want to go beyond surface-level Q&As, these interviewing tips will help you foster connection, authenticity, and unforgettable conversations.

1. Start with curiosity, not an agenda

The heart of every great interview is genuine curiosity. While it’s important to be prepared, don’t go in just to check off questions. Go in to learn about the person you’re interviewing.

Try this:

• Approach your guest like a person you want to understand, not a topic you want to cover.
• Let your curiosity guide the flow instead of sticking rigidly to a script.

2. Create psychological safety

Guests won’t open up unless they feel safe. Connection begins when people feel seen, respected, and unjudged.

Tips to build safety:

• Begin with warm, low-pressure questions to ease into the conversation.
• Let guests know you’re not here to expose them, you’re here to connect.
• Share a bit of your own vulnerability early on.

3. Ask open-ended, thoughtful questions

Great interviewers avoid yes/no questions. Instead, they invite reflection, story, and nuance.

Examples:

• “What’s a moment in your life that changed how you see things?”
• “What’s something you’ve unlearned that surprised you?”
• “Who shaped who you are today?”

Avoid:

• “What do you do?”
• “Do you like doing that?”

4. Practice deep listening

The best interviews feel like conversations, not interrogations. Deep listening allows you to pick up on emotional cues, interesting tangents, and unspoken meaning.

To listen deeply:

• Don’t interrupt or rush to the next question.
• Reflect back what you heard: “It sounds like that was a turning point for you…”
• Leave space. Silence often invites something deeper.

5. Be present, not perfect

Your energy matters. If you’re distracted or trying to perform, your guest will feel it. Authentic connection requires presence.

Try this:

• Before hitting record, take a deep breath.
• Let go of trying to sound “smart” or “professional.”
• Show up as a curious, kind human first and a host second.

6. Follow the emotion, not just the timeline

Sometimes the best moments happen when you stray from the script. If a guest lights up or gets quiet, follow that thread.

Connection tip: When emotion shows up, pause. Gently explore. That’s where meaning lives.

7. Reflect, don’t redirect

If a guest shares something vulnerable, don’t change the subject. Reflect, validate, or ask a follow-up.

For example:

• “That sounds like it was really difficult. How did you get through that?”
• “I appreciate you sharing that.”

This not only deepens trust, but also makes your interviews more resonant.

Real connection in action: So Many Questions…

If you’re looking for an example of these tips in practice, check out the podcast So Many Questions… hosted by Kendall Guillemette.

Each episode features thoughtful, often funny conversations that dig into who people are beyond what they do. The interviews aren’t rushed or rehearsed. They’re curious, compassionate, and genuinely human.

The best interviewing tips aren’t about clever tricks, they’re about showing up with care, curiosity, and a willingness to really listen. When you do that, you create the conditions for real connection and that’s where the magic happens.

Whether you’re just starting out or refining your style, remember: people may forget your questions, but they’ll always remember how you made them feel.