This chapter presents a practical, hands-on AI Strategic Readiness Workshop designed for IT managers and business leaders to evaluate their organization’s ability to adopt and scale AI effectively. Through guided worksheets, scoring models, and pilot planning templates, it helps participants identify gaps, prioritize use cases, and create an actionable roadmap for responsible AI adoption. By the end of this workshop, organizations will be equipped to align AI initiatives with business objectives, mitigate risks, and accelerate value realization.