How Was Your Break? Urghhh… How To Make Questions More Interesting

Hey folks, welcome to the new year. It’s great to be back in the writer’s chair after a couple of weeks off.

So, how was your break?

If you just cringed a little, I get it. Me too.

I was reminded of this typical social interaction when reading Chad Littlefield‘s latest post, in which he argues that there are better, more engaging and novel ways to approach this topic. Questions such as:

  • Tell me about one photo-worthy moment you experienced during your break.
  • Describe a highlight from your break this year?
  • What was something small but memorable that happened over the break?

Then, this got me thinking about how lazy we sometimes are when facilitating groups…


Much the Same As… So, What Did You Learn?


We sometimes ask lazy questions such as “What did you learn from this experience?” and “What did your group do well?” etc, etc. And then we wonder why the eyes of our groups glaze over when we sit in circles and pose these questions.

Just like Chad, I am not suggesting that every interaction you have with a passerby – or a debriefing session with your group – involve a deep, meaningful conversation. But I do think we are called to make questions more interesting, novel and engaging on more occasions.

Yes, it can be a real (social) risk to ask more engaging questions because most people (not you, I’m sure) appear to wander around with their auto-pilot switched on most of the time. So, when you ask a question different from the norm, it may jolt them out of their comatose condition to have to really think about their response.

Happily, when you truly stop to listen to their response, the upside is that this person may feel genuinely seen and heard, which is a good thing and may help build a connection.


My Challenge for 2023


Curiosity is my #1 strength. It helps me succeed as a group facilitator, author, friend and partner. Consequently, I ask a LOT of questions a lot of the time.

My challenge heading into this new year is to exercise this curiosity by crafting my questions to make them more interesting, novel and engaging.

Starting now…

Q: What is one question you wish someone would ask you?

If you feel inclined, share this question by adding a Comment below.


Comments (6)

  1. Cian Brown

    Hey Mark! Great post. I encourage students and clients to reflect on a TMOJ – ‘Tiny Moment of Joy’ and share with me or the group what their TMOJ for the day or activity was.

    • Mark

      Love it, thanks for sharing. I hope you had many TMOJ today 🙂

  2. Martin Botha

    A question that I would like to be asked after doing a session is:
    Describe a moment during our session that made you smile. What were you thinking?

    • Mark

      Terrific question, Martin. I think the key to your question is that you are not asking for the “best” or “most important” lesson but for just “a” lesson. This reduces the pressure on your participants to get it right.

  3. Mary Henton

    Agreed whole-heartedly here. It’s important to ask questions that push the thinking a little, create other ways to look, reflect, or analyze. Thanks for this reminder.

    Talk about a time where/when you hit a turning point. (could be a life-type question, could be reflecting on an activity or process, group or individual).

    • Mark

      I would expect nothing less from you, Mary, thanks for sharing. HNY 🙂

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