Our entrepreneurial group has been meeting since around 2008. Thirteen people, nearly two decades of gatherings. But here’s what actually happens over time: people gravitate toward those they’re already closest to. The same clusters form. The same conversations repeat.

The one-on-one round robin requirement changed that.

With 13 people, that’s 78 unique meetings. Each person had 12 conversations to complete. Some asked if meeting with two others at once would count – I said no. Three people is social. Two people is meaningful.

I tracked it all in a Google spreadsheet (names changed below for privacy). Visual accountability matters – you could see throughout the year where we stood.

We hit 92%. Seventy-two out of 78 meetings happened.

It took some coaxing. Being required to sit down with someone you might not ordinarily spend time with pushes you out of your comfort zone. But almost everyone took it seriously, and many reported genuinely great conversations.

I certainly did. I got closer to people I’d known for years but hadn’t really known. I learned things about them – and about myself – I never would have discovered in group settings.

Here’s what surprised me: relationships don’t deepen automatically, even after decades. You need structure. Left to chance, we default to familiar patterns. But give people a framework and accountability, and they’ll do the thing that actually strengthens the group.

We’re keeping the spreadsheet with each year as a new tab. My 2 year term as president ends today, but hopefully the structure lives on.