The Hard Choices board game from the Software Engineering Institute is a game designed to teach the effect of technical debt in software development. Players choose between taking a shortcut or taking the "long way" and gathering more tools. Shortcuts incur a -1 movement penalty on subsequent turns unless one turn is spent "refactoring."
An interesting suggestion from the Facilitator's guide is to play multiple rounds, keeping the shortcut and tools cards from the previous round. This simulates a second release where shortcuts from the first round will continue to slow development.
I want to play this with my development team but I am not sure how well the will take to playing a dice game in the office. The discussion following the game is likely to be the most important part.
ink jet films and stuck the board on a piece of poystyrene board and the tool cards onto some thick card.