How Do You Create More Meaningful Conversations?

Why most conversations stay shallow

Default questions get default answers. "How are you?" "Good." "How's work?" "Busy." Nobody is being evasive; the question simply did not ask for anything. Change the question and the conversation changes with it.

Four things that make a conversation go deeper

1. A specific question instead of a general one.
2. A follow-up question that proves you heard the answer.
3. Appropriate vulnerability — going first, slightly, so it is safe for them to.
4. Removing distraction. One visible phone changes what people will say.

15 questions you can actually use

At work

• What's taking up most of your energy right now?
• What part of this project are you least sure about?
• What would make the next month easier for you?

At a networking event

• What are you working on that you're actually excited about?
• How did you end up doing this?
• What's changed most in your industry this year?

With friends

• What's been good lately that you haven't told anyone about?
• What are you looking forward to?
• What's something you changed your mind about recently?

With someone you just met

• What brought you here tonight?
• What do you spend your time on outside of work?
• What's the best thing that's happened this year for you?

As a leader

• What's something we should be talking about that we're not?
• What do you need from me that you haven't asked for?
• What's working well enough that we should protect it?

How to listen so the answer gets better

• Pause two seconds before you respond.
• Ask "what do you mean by that?" instead of assuming.
• Reflect the answer back in your own words once per conversation.
• Resist telling your matching story until they are finished with theirs.