When The Penny Drops: Learning What's Not Taught is filled with anecdotes of people in similar situations, and their experiences.

The book is divided into four parts. The first part looks at the author's own career, spanning forty years, in the field of management. The book uses this as a starting point for the rest of the text.

The next three parts looks at the different aspects of personal and work factors that managers have to deal with. The author classifies these as the inner world, the world of relationships, and the world of getting things done.

The inner world is the personal aspect of life. The author stresses the need for a person to take care of themselves. They have to take care of the physical, psychological and spiritual self. He suggests that people should treat their body like they would treat their car, their only car. Always keep it fit and in good condition, and give it adequate rest.

The psychological self needs care in other ways. The author explains the need to do a job with enjoyment, knowing when to let go, and learning to deal with unfairness. Putting in all the effort to realize one's full potential is one way of caring for the spiritual self.

In the world of relationship, the book explains the need to cultivate good communication skills and to avoid misunderstandings. While discussing the execution part of a manager's job, the author suggests that at least at the beginning of their careers, managers should be more of an executive than a strategist. The visionary stage comes later.