When we think about team building, it’s often imagined as a one-time event, a single day packed with activities, connection, and maybe even some laughter. But then Monday comes, and everyone goes back to their separate worlds, inboxes, and task lists.
That’s how most organizations treat team building: an offsite event, not an ongoing practice.
But what if building connection was more like fitness?
The Fitness Metaphor for Team Building
If you wanted to lose 25 pounds, you wouldn’t go to the gym for 12 hours on Monday and eat nothing all day. That’s a recipe for burnout and pain.
Instead, you’d probably take a walk now and then, swap a salad for a hamburger occasionally, and build small habits over time. Those little, consistent actions are what actually lead to transformation.
Team building works the same way. It’s not about one giant, feel-good event, it’s about small, intentional moments of connection that happen regularly and sustainably.
Introducing: Calendar Questions
This exercise, called Calendar Questions, is designed to help you build stronger connections over time, one meeting at a time.
Here’s the big idea:
When you’re together as a team, look at your meeting cadence and decide how you can integrate intentional connection before your regular content.
Because connection before content isn’t small talk.
It’s not “How was your weekend?” or “How’s the weather?”
It’s five minutes that reconnect you to why you’re there, to understand your purpose, values, and shared mission.
Doing that consistently, even just a few minutes each week can help your team stay cohesive, energized, and purpose-driven long after the offsite ends.
How to Run the Calendar Questions Exercise
This one is beautifully simple, and you can do it right now.
- Pick a Question:
Choose a meaningful question from a deck like We! Connect Cards or We! Engage Cards. For example:- “What brings you joy?”
- “When do you feel most aligned with our team’s purpose?”
- “What does success look like for you this month?”
- Schedule It:
Ask everyone to open their phone or laptop and literally create a calendar event.
Example: “Create a calendar appointment on November 3rd titled ‘What brings you joy?’” You can use Siri, Google, Alexa, or your favorite reminder app. - Forget About It (for now):
In the weeks to come, that question will pop up, maybe right before a big meeting or a check-in and it’ll remind your team to reconnect before diving into the to-dos. - Repeat Monthly (Optional):
Want to build a culture of connection? Pick one Calendar Question per month. Over time, you’ll naturally strengthen relationships and improve team dynamics.
Why This Exercise Works
This is one of those fun and simple icebreakers for meetings that scales beautifully. It works because it:
- Makes connection sustainable: You’re building small rituals instead of one-time events.
- Integrates values into your workflow: It’s connection with purpose.
- Promotes mindfulness in meetings: A short reflection before content changes the tone and engagement level of the whole session.
- Fosters accountability: When it’s in your calendar, it’s real.
And yes, this one might cause a short-term “cortisol spike” as you open your calendar amidst all your notifications but it’s worth it. Because you’re not just scheduling tasks; you’re scheduling what matters.
The “Meal Prep” Metaphor
My wife and I have been talking about meal prepping on Sundays for 11 years (batch cooking food for the week) but it never seems to happen….
The ideal version of connection before content is like an actually successful meal prep:
You invest time upfront to plan and set intentions, and it pays dividends all week long.
So when you’re in the same room with your team, take five minutes to set these intentions and schedule those moments of connection now.
Because when your values show up on your calendar, they start to show up in your culture too.
Keep Building Connection
Try the Calendar Questions exercise with your team this week and if you want more facilitation tools, prompts, and exercises like this, explore:
- Ask Powerful Questions — Chad and Will Wise’s bestselling book on creating connection through conversation.
- Connection Before Content Masterclass — a guided program for facilitators and leaders who want to strengthen team culture through better conversations.
- And download free printable cards, book excerpts, and facilitation resources at weand.me/tools.
