In this article, Richard Busby explores the fundamental questions that strategic leaders must ask before making decisions. Through a business story from his early career, he illustrates the importance of assessing tradeoffs and the rationale behind recommendations. Busby shares a decision model developed to justify training solutions for an underperforming insurance claims team. He emphasizes the need for leaders to balance the "can we?" and "should we?" aspects of decision-making, considering both benefits and risks. The article provides actionable steps for evaluating current and proposed projects, encouraging leaders to document their perspectives, challenge low-value work, and leverage the Dutcher Principle to avoid inefficiency. Ultimately, Busby underscores the value of strategic questioning in effective leadership.