A person plays Monopoly, the famous board game, moving a piece across the board indoors

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At Event Garde, we spend a lot of time helping organizations create meaningful engagement experiences, but recently, our own team took a closer look at how we could foster more intentional connection internally as well.

As a remote team, our monthly meetings are often packed with updates, timelines, priorities, and problem-solving discussions. While those conversations are important, we also recognized the value of creating space for relationship building outside of day-to-day project work.

To support that goal, we began incorporating extended personal check-ins into our team meetings every few months. These conversations create dedicated space for team members to connect more personally, learn more about one another, and spend meaningful time together beyond quick work-related updates.

Last month marked our first extended check-in, and we decided to approach it through gamification.

Using our virtual collaboration platform, Miro, one of our team members created a digital version of “Guess Who?”

For the activity, team members partnered up to guess which teammate was being described. Instead of limiting ourselves to simple yes-or-no questions, we intentionally made the game a bit more challenging by asking open-ended questions that encouraged conversation and curiosity. The people being guessed were all members of our own team, which added a more personal and engaging element to the experience.

The activity itself lasted only about 10 minutes, but the impact was noticeable. We laughed, learned new things about one another, and created a lighter, more connected atmosphere before transitioning into the more agenda-heavy portions of the meeting.

What made the activity especially effective was how simple and low-lift it was to execute. It didn’t require extensive planning, expensive tools, or a large time commitment, yet it created an opportunity for authentic interaction that can sometimes get lost in fast-paced virtual work environments.

Recently, one of our clients used a similar philosophy during a team retreat by incorporating structured team-building conversation cards into their programming. While simple in format, the activity created meaningful opportunities for collaboration, reflection, and relationship building across the group.

The card deck guided participants through several stages of conversation, beginning with lighthearted icebreakers before gradually moving into deeper discussions around values, experiences, communication styles, work preferences, and team dynamics. The progression helped participants ease into conversation naturally before moving into more authentic dialogue.

Some prompts encouraged laughter and storytelling, while others helped team members better understand how their colleagues prefer to communicate, collaborate, problem-solve, and stay motivated. Additional prompts focused specifically on team functionality by exploring what was working well, identifying opportunities for improvement, and encouraging open, constructive conversation in a low-pressure environment.

What made the activity particularly impactful was its versatility. The cards supported multiple goals at once: fostering trust, strengthening empathy, improving communication, reducing friction, encouraging participation, and helping individuals feel more understood and connected within the team.

Exercises like these also create opportunities for quieter team members to contribute in ways they may not during traditional meeting formats. By providing structured prompts, the activity encouraged more balanced participation and helped conversations feel intentional rather than forced.

Both experiences served as reminders that gamification does not need to be elaborate to be effective. Small interactive moments, whether incorporated into a retreat, onboarding process, monthly meeting, or team offsite, can have a lasting impact on team culture, collaboration, and engagement.

In environments where schedules are full and agendas are demanding, intentionally creating space for connection may be one of the simplest and most valuable investments a team can make.

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