Building Connection Through Thoughtful Questions

I love a good icebreaker, though I'm fairly certain I'm in the minority. During the pandemic, I found myself managing a newly formed, diverse team while we all worked from home during an uncertain time. I think it's safe to say we all felt a longing for those spontaneous watercooler conversations or lunch breaks with colleagues that naturally broke up our days. Unfortunately, those moments were no longer an option.

So, I decided to start my weekly team meetings with a thoughtful prompt before diving into our work agenda. Each person could take a few minutes to share their response before we moved on to business. My criteria for choosing questions were deliberate. Were they open-ended enough to be revealing? Were they personal enough to build connection while remaining safe? Could the question prompt a short story that would create stronger bonds? Was the topic relatable to everyone in the group so no one felt excluded?

I would ask questions like:

• "If you could spend the day as CEO of any company, which would you choose and why?"

• "Take me back to high school, what was that experience like for you?"

• "What's a special skill or talent you have that very few people know about?"

This was our way to get to know one another without being invasive. Initially, these questions were met with silence and blank stares. But slowly, what began as a chore to appease me transformed into something joyful. A time to truly see and be seen. Over time, this ritual became an anticipated part of our meetings, allowing each of us to be known in ways that weren't possible when we were just discussing project details through a screen.

Now, keeping a list of conversation starters has become part of my routine. Whether I'm meeting a friend for coffee or facilitating a group session at work, I consider which questions might serve to strengthen relationships. Here are some I've been drawn to lately:

• "If you could have any superpower to make your job easier, what would it be?"

• "What's your go-to productivity hack or life tip?"

• "What physical possession do you value most?"

• "If we met a year from now, what would we be celebrating?"

• "What's one thing you've learned this past year that surprised you?"

• "If you could instantly become an expert in any skill, what would you choose?"

• "What's something you're excited about right now?"

• "What's something you've been meaning to try but haven't yet?"

• "If you could have dinner with anyone, living or dead, who would it be?"

• "What's the most beautiful place you've ever been?"

• "What's your definition of a good life?"

• "What was your first job and what did you learn from it?"

• "What's something that made you smile this week?"

Just anticipating about how people in my life might answer these questions brings a smile to my face. I'd be delighted if these inspired you to inject more personality into your upcoming gatherings, whether they're for work or personal connection.

____

Brooks, David. How to Know a Person. Random House, 2023.

Parker, Priya. The Art of Gathering: How We Meet and Why It Matters. Riverhead Books, 2018.

Rothkopf, David. The Great Questions of Tomorrow. Blue Rider Press, 2017.