Picture a room full of people who used to matter enormously to each other (former colleagues, classmates, collaborators) now standing in clusters, wine in hand, running out of small talk. Someone checks their phone. Someone else glances at the exit. By 8 p.m., half the room has left. By morning, nobody can remember what they talked about.
After decades years working at the intersection of communications, engagement, and experience design, I’ve watched organizations make the same costly mistake: they plan events as if logistics are the experience. They book the venue, set the agenda, choose the menu, then assume the connection will just happen. It won’t. This is not a people problem. It’s a design problem.
What’s really at stake
For mission-driven organizations (associations, nonprofits, coalitions, advocacy groups), gatherings are key engagement opportunities. They’re where trust is built or lost, where members decide whether to renew, volunteer, donate, or walk away quietly. If your annual conference or reunion falls flat, not only will you lose momentum, you’ll risk eroding the relationships that make your mission possible.
How to reignite genuine connection when the spark has gone out
I was recently asked to help design the 25-year reunion for a cohort of 100 business school graduates. They were dispersed across the globe. Most had left town over 2 decades ago. Some would barely recognize each other’s names.
I started with the end in mind: when this weekend ends, what do we want people to feel, see, and do?
From there, three separate events were designed, each with its own distinct purpose. The first was low-stakes, deliberately easy to say yes to, designed only as a warmup. The second flooded people with shared memory. The third rebuilt the network with intention.
To spark real connection and restore this network, I used these design principles:
Start with a journey, not an agenda. Connection doesn’t happen all at once. Set a welcoming tone through pre-event communications. Then build momentum gradually. We started with a gathering that didn’t require commitment or a big investment. The next two events went deeper. People stepped out of their comfort zone, leaned in and made the most of the experiences right until the final toast.
Hold space for small groups. As the audience grew from 20 to 40 people, each event was structured around clusters of 6 to 10, while inviting newcomers to join with ease. Quirky, personalized name tags, conversation-starters on tables, and intimate seating were signals: be yourself, start where you’re comfortable.
Protect the human moments. Our cohort is always online, so we went deliberately analogue: human to human, low-tech, sensory, and nourishing. The moments people talked about afterward were the unexpected conversations, the laughter over old photos, the singalong, the handshake that turned into a collaboration. For those who couldn’t make it, a post-event video reel and photo montage invited everyone to experience highlights from the weekend.
Design for interaction, not information. Over 12 hours together, only one was structured as sit-and-listen (during the campus tour). The rest was designed for interaction, adding information selectively without breaking up conversations. Instead of one emcee, we invited different voices to guide the group through each event.
At our final dinner, the cohort had shifted. They exchanged contacts, shared photos of their kids, scheduled follow-up meetings and stayed around until the venue closed. They also rose to the occasion for a big finale: a nostalgic group singalong! That’s the moment I knew we had genuine connection.
What most organizers miss with in-person events
Here’s what I see too often: a committee spends months on logistics and 20 minutes on participant experience. The result is an event that’s technically flawless, but makes no emotional connection and is easily forgotten. Speakers fill time slots. Networking is left to chance in a loud lobby. People leave with a tote bag and no new relationships.
Engaging experiences designed with purpose
If you’re planning an annual event, monthly member gathering, a board retreat, or a stakeholder convening, I’d love to help you design it from the ground up. We’ll start with purpose, not logistics.
My Experience Design Sprint is a focused, collaborative engagement where we build your event experience together: from connection architecture and session design to facilitation guides and measures of success.
Don’t go back to your old template. Your people deserve more than an event they’ll forget by Friday.