Practicing project management is much like playing poker: One must balance the risks of failing against the odds of winning. Understanding this dynamic can help project managers more effectively convince their organization's executives to invest in project management initiatives. This article discusses how project managers should approach their attempts to secure project funding from executives. In doing so, it identifies the key factors that influence an executive's decision to accept or reject an opportunity to invest in a project. It also lists eight questions that can help project managers sell investments in project management to executives.