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The intricacies of IT strategic planning come with inherent risks, differing across traditional top-down, agile, and hybrid methodologies. This chapter unveils the challenges present in each approach, from potential disconnects between executives and implementers in top-down planning to communication lapses in agile strategies. Crucially, readers will gain insights into actionable strategies to mitigate these risks, emphasizing the pivotal roles of clear communication, strategic-tactical alignment, and flexibility. Dive in to equip your organization with the knowledge to navigate IT strategic planning challenges successfully.