IT Project Management: Lessons Learned from Project Retrospectives 1999–2020

Companies realize they cannot stay in business if they cannot manage their projects effectively. Yet, most organizations still are either unable or unwilling to perform the one basic activity critical to project management and continuous improvement: learning from mistakes and successes. This monograph provides a framework for conducting retrospectives—a process of “looking back†—to glean lessons for ongoing and future project success. This systematic approach has evolved through the analysis of hundreds of information technology (IT) projects over the past 20 years. Compiling the findings of this extensive research, the monograph offers a guide for how to leverage best practices to avoid classic mistakes with the end goal of improving the chances of project success. To this end, the monograph begins with a discussion on project retrospectives, including what they are, why they are important, and why they aren’t done, followed by a description of the action research (i.e., meta-retrospective) on which the remainder of the monograph is based. The focus of Section 2 is on 10 of the most infamous IT project failures (each with reported losses of over $100 million), a ranked list of classic mistakes that most often contribute to project failure (categorized by people, process, product, and technology), and a discussion of one method (root cause analysis) and five best practices designed to prevent classic mistakes from occurring in the first place. Section 3 presents a robust framework for evaluating project success based three process-related criteria (schedule, cost, and product) and three outcome criteria (use, value, and learning). Section 4 defines momentum as it relates specifically to IT projects and discusses how managers can equip themselves with mapping and analysis tools to control the momentum of a project for best results. The focus of Section 5 is on the most cited reason for IT project failure—poor estimation. Using the findings from two research studies, the section provides recommendations to help project managers improve project estimation. In sum, this monograph plots a pathway to success for IT project managers by applying the voluminous findings from analysis of retrospectives done for 264 IT projects from 1999 to 2020. The result is a comprehensive guide that project managers may use to gauge progress at points throughout a project’s life, map momentum, apply best practices to spot and prevent classic mistakes, conduct root-cause analysis, and devise actionable recommendations that will help their organization achieve project success.