Monopoly notwithstanding, most board games don't yield direct business insights.
Here are three exceptions, courtesy of software entrepreneur and veteran gamer Matt Calkins.
The game: Players try to accrue the most points by bidding for land along the Nile in ancient Egypt. Different provinces have different properties. Begin by acquiring land hospitable to agriculture, and you may struggle to erect pyramids later in the game.
The insight: Strategy doesn't happen in vacuum. When making a decision, consider how it will limit or expand your choices down the road.
The game: Players build, invest in, and merge hotel chains, with the goal of making the most money. Opponents' stock and cash holdings are secret. You can change the game by attacking your opponents at the exact moment when they lack cash to defend their assets.
The insight: Strategic opportunities appear in brief windows of time. Be ready with the vision and resources to capitalize on them.
The game: Calkins created this one himself to model the experience of launching a start-up. It's set in the early days of aviation. Players compete to build the most successful airline by reducing inefficiencies and exploiting new technologies while mitigating the impact of crashes, strikes, and oil shocks.
The insight: Good entrepreneurs develop capabilities while insulating themselves against misfortune. Always be heding.