Why so many board retreats fall flat – and how to fix that

A senior leader from a large nonprofit reached out about designing a retreat for one of their key departments. Here’s what struck me:

• The retreat was just two weeks away.

• A handful of team members had already been tasked with designing the day.

• Each person had ownership over one chunk of the agenda—and they hadn’t been in touch with each other about plans or possibilities.

• And, there was a palpable sense of uncertainty about what the retreat was actually supposed to accomplish.

The agenda felt cobbled together: a series of disconnected sessions, each designed in isolation, with no shared understanding of how they were supposed to roll up into something meaningful.

Moreover, the sessions were far too ambitious for the time available. Important questions would get shortchanged. Conversations would be rushed. People would leave feeling like they drank from a firehose—and no one would remember what had actually been decided.

I see this sort of half-baked retreat planning all the time. I’ve even heard people say, “It’s just a long meeting—how hard could it be to put together?”

The truth is: it takes real work, intention, insight, and foresight to design a powerful retreat that converts possibility into action.

So here’s what I told the planning team:

Before you carve up the day and assign pieces, get crystal clear on your desired outcomes:

• What do you want to have in hand by the end of the retreat?

• What decisions need to be made?

• What would make people say, “That was absolutely worth our time and expense”?

Only once you know the destination can you design a structure to get you there. Start with the outcome, then design your way there–with care.

A successful retreat requires intention, integration, and sequencing:

• The right people need to be in the room.

• Conversations and activities should build on each other.

• Data must show up at the right time. Decision points should be clear.

• Pre-work must set the stage for progress.

And please—don’t design in siloes. If each session is designed independently, what are the odds the pieces will magically fall into place? (Spoiler: they won’t.)

When I design retreats, I typically spend 2–3 hours planning for every one hour in the room–aligning goals, sequencing conversations, perfecting discussion prompts, and looking around corners to prevent confusion before it starts.

Yes, it’s an investment—in time, in expertise, and in budget. But that’s exactly how I deliver the value I’m known for: thoughtfully crafted, deeply engaging, strategically effective convenings that align collaborators, spark insight, unlock decisions, and build real momentum.

Takeaway Tip: If your retreat planning starts with “Who wants to run which part?”—hit pause. Instead, start with: “What are we here to accomplish?” Then build your day with that end point clearly in view.

Is your board or organization gearing up for a retreat? I’d be glad to talk through your goals and explore how I can support your success. Just hit reply to start the conversation.