This longitudinal study examines information technology management issues that senior IT executives have indicated to be the most critical to their organizations over a four-year period. Through association rule mining, it provides a comprehensive view of issues that persist and vary together over time. Findings provide insight into better leverage resources in managing these issues holistically. For example, there appears to be a stronger synergy among issues in three key areas of IT focus (transformation, strategy, value) than previously understood. The ability to leverage this synergy could lead to even greater ability for organizations to leverage and capitalize on IT for success.