The Art of Asking Questions That Open Doors

Les Giblin often said, "The art of conversation is not about what you say—it's about what you ask." In a world where everyone wants to be heard, the person who asks great questions holds remarkable power.

Why Questions Matter

Questions do three powerful things simultaneously:

1. They show genuine interest in the other person
2. They give you valuable information
3. They make the other person feel important

Most people spend conversations waiting for their turn to talk. When you ask thoughtful questions instead, you stand out immediately.

The Question Hierarchy

Not all questions are created equal. Giblin identified a hierarchy:

Level 1: Closed Questions
"Did you have a good weekend?"
These get yes/no answers. Use sparingly.

Level 2: Open Questions
"What did you do this weekend?"
These invite longer responses but can still feel routine.

Level 3: Curious Questions
"What was the best part of your weekend?"
These show genuine interest and invite meaningful sharing.

Level 4: Follow-Up Questions
"What made that so special?"
These demonstrate you're truly listening and want to understand more deeply.

The Follow-Up Is Everything

Here's where most people fail: They ask a good opening question, get an answer, then immediately pivot to their own story or a new topic.

The magic happens in the follow-up. When someone shares something, ask them to tell you more. Show curiosity about the details. Let them expand on what matters to them.

Questions to Avoid

Giblin warned against several types of questions:

• Interrogation questions that feel like an interview
• Leading questions that push your agenda
• Multiple questions that confuse the listener
• Why questions that can feel accusatory (use "what" instead)

The Power of Silence

After asking a question, resist the urge to fill the silence. Give people time to think and formulate their response. Some of the best insights come after a pause.

Practice Questions

Try these conversation starters that Giblin found particularly effective:

• "What's been the highlight of your week?"
• "What are you most excited about right now?"
• "What's the biggest challenge you're facing?"
• "What would you do if you weren't worried about failing?"
• "What's something you've learned recently?"

The Ultimate Question

Giblin's favorite question, which he used in countless situations: "How can I help?"

This simple question communicates respect, generosity, and genuine interest. It shifts the conversation from transactional to relational.

Making It Natural

The goal isn't to memorize questions or sound like you're following a script. The goal is to develop genuine curiosity about other people.

When you're truly interested in understanding someone, the right questions flow naturally. And when you ask them, people open up in ways that create real connection.

Start today: In your next conversation, ask one more follow-up question than you normally would. Notice what happens.