The rapid increase of new and emerging technologies, the considerable costs associated with implementing technological solutions and the budget constraints of healthcare organizations combine to emphasize the importance of thoughtful consideration of any information technology (IT) purchase. Given their role in deciding whether or not to invest in a specific technology, healthcare executives are instrumental in this process. While there is no need for everyone to have a technical background, asking the right questions helps healthcare executives understand the full impact of the proposed solution. Here we present 10 questions healthcare executives should ask prior to investing in IT projects. These questions and the supporting background are based on our collective experience as information management/IT leaders in the healthcare industry combined with findings from the relevant literature.