What are the proposed IT initiatives? What questions still need to be addressed in the systems planning and systems analysis phases? Why: Why are you proposing these IT initiatives? How will the IT initiatives support or enable the business objectives? How Much: What is the high-level cost / benefit of each initiative? What are the timing and priorities for your multiple-year plan? What is the timing for implementation of each initiative? In what order do you propose the IT initiatives be implemented? Why are you proposing that order? Who: What is your recommendation for who will implement the initiatives (in-house resources, contractors, software providers, a combination, etc.)? Where: Will the initiatives be run in-house or be implemented as a cloud computing solution? How: How will you measure success? What will be checkpoints to determine if the strategy is on track?