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Embarking on a comprehensive exploration of IT strategic planning, this chapter offers an insightful journey into various approaches, from traditional to agile to hybrid planning methods, highlighting their unique advantages and limitations. Through real-life case studies, readers gain a nuanced understanding of how different strategies align with specific organizational goals, cultures, and market environments. The text emphasizes the criticality of stakeholder engagement, effective change management, and the continuous improvement mindset, underlining the importance of regular reviews and benchmarking. Additionally, it touches upon the role emerging technologies like AI and IoT will play in shaping the future of IT strategy. Readers will walk away not only with a foundational understanding of current IT strategic planning practices but also with an eye on the horizon, ready to anticipate and embrace future trends in the field.