Service on a college or university board of trustees has always been an honor, and still is. It has always entailed significant responsibilities, and still does. At a time of rising expectations and diminishing resources, of profound demographic and cultural change, of global opportunities and global competition, trustees are called to think strategically about their institutions. From a 20-year perspective as a senior administrator working with boards of trustees and as a current trustee herself, the author knows that most trustees are familiar with and comfortable with strategic-planning processes, whether those processes are generated internally or mandated by external agencies, such as state legislatures. But she has also found that the trustees most committed to detailed strategic plans and to predictable and precise execution of those plans are also often those least capable of strategic thinking. And for that reason, despite their good intentions, they find it difficult to acknowledge the need for transformational changes. In this article, the author makes the case for strategic thinking as a driver of transformational change. From personal experience, she offers examples of what happens when strategic thinking at the board level drives specific campus plans and what happens when it does not.