38 executives at the Great Lakes Winter Roundtable

Thirty-eight association executives filled the Great Lakes chapter's Winter Roundtable on February 8, meeting in a conference room at 55 Wacker Drive with the frozen Chicago River visible through the windows. The event is capped at 40 seats, and this year's session came within two of selling out — the closest the roundtable has come to capacity since the chapter began tracking attendance.

The roundtable is a fixture of the Great Lakes chapter's calendar, held every February for association executives from member organizations across the region. The Great Lakes chapter counts 98 member organizations, spanning sectors from water utility engineering to food-bank network management, and the roundtable draws a mix of small-staff executive directors and larger association CEOs.

Wendell Szymanski, executive director of the Great Lakes Maritime Shippers Association in Cleveland, was among the returning attendees. His association represents 85 shipping companies with a staff of six, and he said the roundtable is one of the few places he gets uninterrupted time with peers running similarly small operations.

"I've been coming to this one since it started," Szymanski said. "You get more out of two hours around a table with people running similar-sized shops than out of most conferences. Nobody's trying to sell you anything, and nobody's pretending their office has more staff than it does."

Attendees split time between two topics: succession planning for small executive teams and how member organizations are handling dues increases without losing renewals. Facilitators ran the session in small round-table groups of six to eight, rotating topics every 40 minutes so each attendee touched both subjects.

Several attendees raised the same concern from different angles: association boards that assume a long-serving executive director will simply be replaced when the time comes, without a transition plan or a named successor in training. The conversation echoed themes NANA's national programming has picked up in its own executive-transition planning, including guidance the Foundation and national staff have started building into the Learning catalog.

Chicago saw several inches of snow the morning of the roundtable, and chapter staff reported no cancellations tied to the weather — a detail organizers noted approvingly, given how close attendance already ran to the room's cap.

The chapter's monthly roundtable continues on the third Thursday of each month in Chicago, drawing a smaller recurring group between the annual Winter Roundtable sessions. The next Winter Roundtable is scheduled for February 2025, and chapter staff said they expect to open registration earlier given how quickly this year's seats filled.

Registration for next year's session will open through NANA's chapter portal, and executives from outside the Great Lakes region are welcome to attend if seats remain after chapter members have first choice.

The chapter's other signature programs continue on their usual cadence in the meantime: a 12-month mentorship pairing for staff new to association management, running cohorts starting each March, and the quarterly virtual Finance Officers Circle serving Detroit and Columbus members.