Asking Follow-up Questions

You ask someone how they’re doing. They say, “I’m good.”

Normally, that’s where the conversation ends. 

But maybe you notice something in their expression, and you ask, “You sure you’re good?”
They hesitate. Then they say, “Not really.”

You say, “Not really? Tell me more.”

Maybe what follows is a story about a sick family member. 
Or feeling stretched too thin at work. 
Or something they hadn’t fully put into words, or even realized, until you asked. 
That one follow-up - ”You sure?” - opened the door.

One good question can change a conversation.  

When someone shares an idea or a feeling, most of us do one of two things: we judge it immediately, or we start rehearsing what we want to say next. 

There’s a third option: curiosity.

A good follow-up question invites the other person to go a little deeper. 
And often, when they do, they clarify their own thinking in the process 

In your deliberation, try asking follow-up questions like:

  • “Can you say more about that?”

  • “How do you see that working?”

  • “Are you drawing from experience?”

Follow-up questions surface reasoning that might otherwise stay hidden. 
They uncover tradeoffs. 
They unlock what’s underneath someone's first answer.
They also protect you from filling in the blanks with your own assumptions. 

More importantly, follow-up questions create space for better thinking - yours and theirs. 

That’s how deliberations move from quick reactions to real understanding.

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Paraphrasing

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Avoiding Quick You-Turns