- Nov 26, 2025
- 3 min read
Updated: Nov 30, 2025
Thanksgiving is the start of the Holiday Season. A time when we attempt to slow down long enough to connect with family and friends that we don’t see every day. Because we try hard to avoid topics that might escalate into uncivil conversations, we spend most of our time talking about food, football, and friendly but shallow small talk topics.
This Holiday, I encourage you to try something different. In addition to planning your meal, take a few minutes to prepare a handful of positive questions you can ask people before, during, or after dinner.
A positive question communicates: “I value you, and I want to understand you.”
And when you ask multiple positive questions, you communicate something even more meaningful: “I want to know more about you.”
Unfortunately, most conversations we have these days are like stones skipping across the water, we touch the surface of a topic and then move quickly to another subject. But when you pause, listen a little longer, and ask a couple positive “follow-up” questions, you often discover more:
Common ground
Shared experiences
Opportunities to connect
Reasons to appreciate each other
Stories you’ve never heard before
Information about what truly matters — and why
Memories that brought out the best in them
The Power of Follow-Up Questions
When you ask someone a series of positive questions, you’re inviting them to reflect on a moment that made them stronger, happier, or more hopeful. Those reflections create positive emotions — for them and for you.
Below are three examples of how asking follow-up questions can turn a simple topic into a meaningful story.
1. Topic: A Positive Influence
First Positive Question:
“Who was the most positive influence in your life this year?”
Follow-Up Questions:
“What exactly did they do that mattered to you?”
“How did their support or encouragement impact you?”
“What did that experience teach you?”
2. Topic: An Achievement
First Positive Question:
“What achievement was most important to you this year?”
Follow-Up Questions:
“What made that achievement meaningful?”
“What effort did it take to make it happen?”
“What’s one important goal you want to accomplish next year?”
3. Topic: A Challenge
First Positive Question:
“What challenge did you overcome this year?”
Follow-Up Questions:
“What helped you keep going when it got tough?”
“What did you discover about yourself?”
“How are you stronger or wiser because of it?”
If you believe positive questions can open the door to more meaningful conversations, it helps to have an inventory of them ready. Here are 10 examples for you to review. Select the ones you’d like to ask and add some new ones to the list. Remember to ask a few follow-up questions on the same topic.
What are you proud of that others may not know about?
What is something important you learned recently?
What natural talent did you develop into a strength this year?
What is something new you enjoyed doing this year?
What goals were you most proud of achieving?
What is one of your best memories this year?
What did you do this year that took courage?
Who benefited this year because of something you did?
What is something good that happened that you didn’t expect?
What are you grateful for today?
Positive questions are a powerful gift you give to others.
They help people tell stories about the moments from their past when they were at their best—and every time someone shares one of those stories, they feel a little more hopeful about their future.
Positive questions are also a gift you give yourself.
Each time you ask someone a positive question, you hear a story that lifts your spirit. And each time you pause and answer a positive question yourself, you reconnect with your own strength, courage, and a deeper sense of hope about your future.
So, this year, consider asking and answering more positive questions that bring out the best in everyone. I think your Holiday will be a lot happier and healthier if you do.
Let's Get Better Together,
Bill Durkin, Founder
One Positive Place
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