In recent years there has been an increasing amount of attention paid to effective strategic planning of the information systems resource in many organizations. The motivation for this attention derives from a number of sources, especially the rapid rate of technological progress in computer and telecommunications facilities and the increasing application of these facilities to problem domains that are critical to organizational success. As a wide range of new opportunities become apparent, it has become more difficult to match the operational, managerial, and strategic needs of the business with appropriate systems activities. Based upon an exploratory study of eight organizations which involved extensive interviews with IS and senior managers, this article describes the planning practices observed and identifies several factors which seemed particularly important to their planning success, or lack of it. These factors include such things as the style of senior management decision making, the volatility of the business (and by extension, the applications development portfolio), the complexity of the IS organization and management task, and the status and physical location of the IS manager.