Before You Book the Venue: Five Questions to Ask Before Planning Your Next Leadership Convening

When organizations start planning a leadership convening, the first calls usually go to venues. Then caterers. Then AV companies. The logistics come first because they feel urgent — and because dates, costs, and room setups are easier to act on than the harder questions underneath them. But the organizations that get the most out of their convenings don't start with a venue. They start with a question: what do we actually want this gathering to do?

Here are five questions worth answering before anything else gets planned.

1. What do we want participants to think, feel, or do differently when they leave?

This is the most important question — and the one most often skipped. A convening without a clear intended outcome is just a meeting with better food.

Be specific. "We want participants to feel energized about our new strategic direction" is a starting point. "We want our regional directors to leave aligned on the three priorities they'll be accountable for in Q3" is an outcome you can design toward. Every decision that follows — who speaks, how sessions are structured, what conversations are facilitated — should trace back to this answer.

2. Who needs to be in the room, and why?

Convenings work best when the right people are in conversation with each other. That sounds obvious, but it's worth thinking through carefully. Who has the authority to make decisions? Who has the credibility to influence culture? Whose voice is missing from the conversations that matter? Who needs to build relationships with whom?

The answers shape not just your invite list but your room setup, your session design, and how much time you build in for informal conversation — which is often where the most valuable exchanges happen.

3. What's the one conversation we've been avoiding that this gathering could unlock?

Every organization has them — the strategic tensions, the unresolved questions, the elephants in the room that don't come up in regular meetings because the setting isn't right.

A well-designed convening can create the conditions for those conversations to finally happen. But only if you name them in advance and build space for them intentionally. A tightly scripted agenda with no room for real dialogue won't get you there.

4. What would make this gathering feel different from every other meeting we've had?

If your leadership convening feels like a longer version of your regular staff meeting, you've missed an opportunity.

Think about the physical environment, the pace, the mix of structured and unstructured time, the voices you bring in from outside, the moments of inspiration alongside the moments of real work. The best convenings create a sense that something different is possible — and that feeling is contagious.

5. How will we carry the momentum forward after the event ends?

A convening that generates great energy and then disappears into everyone's inboxes is a missed opportunity. The real value isn't in the room — it's in what happens because of what happened in the room.

Before you finalize your agenda, think about what follow-through looks like. Who owns what? How will decisions get communicated? What's the 30-day check-in? Building that structure before the event means you're not scrambling to capture momentum after it.

The venue matters. So does the food, the AV, the run of show. But those are the easy parts. The hard part — and the most valuable part — is getting clear on what you're really trying to accomplish before any of that gets decided. Start there, and everything else will be easier to get right.

Planning a leadership convening or industry forum? I'd love to think through it with you. Reach out at bovardconsulting.com.