Getting a project approved, or killed, often has less to do with technical merit than with who actually holds the keys and what they need to hear. This talk draws on real case studies from library design fights, cross-functional infrastructure rewrites, and a couple of notable failures to show practical techniques: how to find the real decision-maker, how to break expert deadlock with a position paper, and how to build toward an audacious goal through incremental wins and a well timed crisis.