3 Fun Roundtable Conversation Starter Topics

Mar 26, 2024

In today’s fast-paced world, genuine conversations can often fall by the wayside, replaced by superficial interactions. I’ve dedicated my career to reversing this trend, working alongside some of the brightest leaders and educators globally to foster deeper connections and more meaningful dialogue. Let’s dive into three round table conversation topics that draw on the past, present, and future to spark insightful discussions at your next event, whether it’s a conference, summit, or staff meeting.

The Magic Of The Second Question

Inspiration struck when I stumbled upon a LinkedIn post detailing a unique exercise. Participants, all senior leaders, wrote down their first job on a sticky note. The real transformation came with the second question: “What did that job teach you about being a better leader or boss?” This approach not only encourages reflection but also fosters empathy, prompting leaders to consider the experiences they are creating for their employees.

Enhancing Inclusivity

To make this exercise even more inclusive, I propose a slight modification. Ask participants about their best, worst, or funniest job. This adjustment not only broadens the scope but also taps into a range of emotions, leading to richer, more memorable conversations.

Inviting The Group To Be Present

One of my favorite questions to ask in a group setting is, “What is taking up a lot of your brain space right now?” This question is a powerful tool to help attendees be present, setting the stage for a productive event by acknowledging and sharing the diverse thoughts and concerns they bring with them.

Defining “Belonging”

My interpretation of belonging goes beyond the standard definitions. I believe it encompasses seeing, hearing, understanding, and accepting people for who they are—and who they are not. Midway through conversations, encouraging participants to reflect on the stories being shared can deepen connections and enhance the sense of belonging.

How To Talk Your Way Into Tomorrow

Humans have the remarkable ability to shape their futures through conversation. Asking “What is something you’d like to do more of?” can lead to self-discovery and action. This question helped me reconnect with my passion for scuba diving, demonstrating the power of inquiry in prompting change and fostering growth.

Encouraging Participation Through Inquiry

Research shows that engagement in discussions about a topic can significantly increase the likelihood of taking action related to that topic. This principle can be applied to encourage participation in various contexts, illustrating the transformative power of questions.


Meaningful conversations have the power to connect us, inspire action, and foster understanding. By incorporating these strategies into your next event, you can facilitate discussions that not only engage but also empower participants to reflect, connect, and envision a better future.

For more innovative discussion topics and engaging conversation starters, feel free to explore the resources linked in the description. Here’s to enriching conversations and meaningful connections. Have an amazing day!