It is extremely difficult to overcome what James O'Toole calls "the ideology of comfort and the tyranny of custom." In Leading Change, he explains why organizations and their leaders must not simply change to accommodate new realities; they must transform themselves effectively. According to O'Toole, "today's executives believe they are struggling with an unprecedented leadership challenge to create internal strategic unity within a chaotic external environment ....Executives know what needs to be done and even how to do it. Nonetheless, they are unable to lead change effectively. Explaining the sources of this paradox and offering a practical way to resolve it are the purposes of this book." Leading Change is divided into two parts within which O'Toole addresses three separate but related questions:

1. What are the causes of resistance to change?
2. How can leaders effectively and morally overcome that resistance?
3. Why is the dominant philosophy of leadership, based on contingency theory, neither an effective nor a moral guide for people who wish to lead change.

For O'Toole, values-based leadership is provided by those he calls "Rushmoreans": They possess courage, authenticity, integrity, vision, passion, conviction, and persistence. To vary degrees, "Rushmoreans" listen to others, encourage dissenting opinion among their closest advisers, grant ample authority to their subordinates, and lead by example rather than by fiat, manipulation, or coercion. Granted, history produces very few Washingtons, Jeffersons, Lincolns, and Roosevelts. Nonetheless, according to O'Toole, there is much of value to learned from them by those who struggle with "an unprecedented leadership challenge to create internal strategic unity within a chaotic external environment".