Broad, vague questions are conversation kryptonite.

Yawning young man.

Always asking questions = boring conversations galore.

You’ve all probably heard that one of the best ways to continue conversation and connect deeply is to keep asking questions.

“So what do you like to do for fun?” Who ever has a good answer to that question? Or what your favorite hobby is, or what your favorite music is…

There’s a good way and a bad way to ask questions in conversation. Yes, even questions can be optimized for great interactions.


When you ask broad, vague questions, they stall conversation because they will almost always require someone to step back and think for a second. This throws off their flow, and disconnects them from the prior topics as well. What do I mean?

Tell me about yourself. How are you supposed to answer that, especially off the top of your head? Do they mean your education, upbringing, hobbies, or family?!


So do you play any sports? Much easier to answer, and doesn’t require people to think. It’s literally a yes or no question that people know off the top of their head.

The lesson is simple.

Instead of broad questions about people, ask them specific, pointed questions that they can answer. When you ask broad questions, you put the burden of carrying the conversation on them, and gets tiring and annoying. Specific questions are softballs, so to speak, and simply make it easy and pleasurable for them to converse with you.

Click for my book Improve Your Conversations: Think On Your Feet, Witty Banter, and Always Know What To Say for more tips on crushing awkward silences.


If you haven’t grabbed it yet, click here for FREE access to The Flawless Interaction Checklist – learn how to connect with people, crush awkward silence, and guarantee great conversations.