Meaningful questions that push past small talk!

Written by Scott Herrold. Posted in Uncategorized

Thanksgiving is full of “so how’s work?” and “how’s school?” conversations that don’t really go anywhere. Here are 10 creative ways to ask better, more meaningful questions that draw your relatives out and make for real connection – not just small talk.


1. Ask for stories, not stats.

Instead of “How’s work?” try, “What’s something funny or surprising that happened at work this year?”

Stories bring warmth and connection – facts bring short answers.

2. Ask how they felt, not just what happened.

“What was that like for you?” opens up way more than “What happened?”

3. Go backward before you go forward.

“Tell me about a Thanksgiving memory from when you were a kid.”

People love to revisit moments that shaped them — it invites nostalgia, not debate.

4. Ask about growth, not just goals.

“What’s something you’ve learned this year – even if it was the hard way?” What was it about it that stretched you?

It opens the door for vulnerability without sounding too serious.

5. Replace “Why?” with “Tell me more about that.”

“Why?” can sound judgmental. “Tell me more about that” sounds like genuine curiosity.

6. Use gratitude as an entry point.

“Who’s someone that really encouraged you this year?” or “What’s a small thing you’re grateful for that most people wouldn’t think of?”

7. Keep it light and layered.

“What’s one thing that made you laugh this year – and one thing that taught you something?”

A mix of humor and honesty keeps people engaged.

8. Ask about what matters, not what’s trending.

“What’s been giving you peace lately?” or “What’s been stealing it?”

That goes deeper than sports scores or politics.

9. Let kids and teens lead.

Ask the younger ones: “What’s something you’ve learned about God, life, or yourself this year?”

Their answers are often more profound (and hilarious) than we expect.

10. End on hope, not history.

“What are you most looking forward to in the next season — big or small?”

It turns conversation toward gratitude, anticipation, and joy. Share with your family what is giving you hope about the future!

Scott Herrold

Morning Show Personality/Program Director/Creative Ninja at SOS Radio in Vegas.