One on-going problem within IT that I see is the inability for management and HR to work effectively as a team and develop a competent strategy for hiring, maintaining appropriate staffing levels, training and retaining employees. This comes from a belief that folks in IT do not need training, that a company can hire staff that are ready at the starting gate. This is insane considering how this is not expected in any other field. Take an accounting firm; they factor in training costs for all CPAs they hire, regardless of skill and experience level, this is because they understand the costs of having and retaining educated, competent employees.
This posting by James McGovern hits the nail on the head.