In this chapter, we use the IT staffing cycle of forecasting, acquiring, training, and retaining to investigate how companies ensure that their IT staffs possess a skill base adequate to respond effectively to rapidly changing and uncertain technological environments. To better understand the strategies that companies use throughout the IT staffing cycle, we surveyed 30 senior-level managers (i.e., CIOs, IT planners, and Human Resources managers) from 15 companies representing a broad range of organizational environments across five different industries: energy, high-tech, financial, transportation, and distribution. Telephone interview questions were based on a framework that we developed to explain the relationship between IT and organizational planning in IT skills forecasting. The respondents answers to these questions clearly demonstrate that the companies in our sample lack formal systems for linking business plans with IT plans for the purpose of forecasting IT skills. Further, our study findings clearly suggest that long-term skill needs are not managed, but are treated as a source of uncertainty. Within the skills acquisition process, strategies appear to be adopted with the intent of reducing uncertainty. In particular, companies often treat the IT group as a self-contained unit that operates separately from Human Resources when acquiring employees with needed IT skills from the external market. Staffing gaps are frequently filled by turning to the external market to find IT specialists with needed skills, or by turning to their internal market by training employees already on the payroll. We conclude with suggestions to fine-tune IT skills forecasting and planning.