How to Stop Asking, “How are You?” and Create Real Conversation

Aug 24, 2020

Stop asking stupid questions like:

  • How are you?

  • How are you doing?

  • How are you feeling?

You already know how people are doing. The future feels like mushy spaghetti.

Answers to, “How are you?” sound inane because they are. What’s worse than “Fine”?

What if “How are you?” comes from your heart. Chances of connecting are like a forecast of rain in the Sahara.

Better questions:

  1. What are you working on?

  2. What’s next on your agenda?

  3. What challenges are you facing?

  4. What’s working for you?

  5. What’s new in your life?

  6. What are you looking forward to?

  7. What would you like to get done today?


“Open your eyes before you open your mouth.”

“Let’s say you’re talking to the CEO of a large, iconic company who is about to retire, and you noticed a row of empty boxes along the wall of the CEO’s office. You might start with the question, “How hard is it for you to leave this job?” Gary Burnison, CEO, KORN FERRY

Last interaction:

I’ve been imagining that I’m having my last interaction. (I keep my imagining to myself.) What would you ask or notice if this was your last interaction with someone?

The advantages of a ‘last interaction’ approach:

  1. Deep listening.

  2. Noticing expressions and gestures.

  3. Responding with genuine interest.

I ask about people’s stories when I imagine it’s my last interaction. Recently I asked someone about the first teacher they remember from elementary school.

In another conversation I asked, “What was your most embarrassing moment?” You could ask, “What was your proudest moment?”

How might you have authentic conversations?

What’s the value of having authentic conversations?

Bonus material:

50 Questions to Ask Someone Instead of “How Are You” (Medium)

What to Ask Instead of ‘How are You?’ During a Pandemic (Atlantic)

How to Skip the Small Talk and Connect with Anyone (TEDx)

By Dan Rockwell