As project managers (PMs) play an important role in project success, assigning PMs with appropriate skills and personalities to projects is a crucial task. Nevertheless, empirical research on skill requirements for information technology (IT) PMs is limited and little information systems literature focuses on the role of internally recruited IT PMs. This paper presents a case study of a troubled IT project led by three consecutive PMs, with a range of backgrounds, skills, and personality types. Across subjects, IT project management was found to be a necessity of project success. Additionally, it was observed that internally recruited PMs showed advantages in understanding organisational culture and business processes. Lessons learned from the three PMs confirm the importance of particular skills previously described in the literature, and the need for an additional focus on how an IT PM’s personality facilitates or inhibits IT project outcomes.