Derailed – Book Review


This is one of the best books I have read on the topic of leadership and highly recommend it. Tim Irwin deep dives into the mysterious and captivating topic of executive derailment. He asks the question: why do seemingly bright, capable and ambitious people sabotage their own careers? Irwin provides a synopsis of six leader personalities and the corporate situations that led to their derailment. He also provides strategies for the reader to insulate themselves from meeting their own ‘derailed’ end.

The authors intent is not to poke holes, berate or ostracise the named executives, but to educate us all. Through the media, we come to learn about high profile people derailing. However, ‘normal’ people derail every day. If you don’t run a listed business or country, your derailment will only be known in local circles. It doesn’t make it any less unfortunate or damaging for those involved just because it is not reported in the press.

Derailed: Five Lessons Learned from Catastrophic Failures of Leadership Book Review
Thanks to Tim Irwin and Thomas Nelson


Derailment occurs before the crash

I found this explanation particularly insightful. The author explains that derailment actually happens before the crash. It occurs over time. A series of signals that the leader ignores – feedback they don’t listen to, warnings from advisors are ignored, emotional cues missed and a slow onset of hubris. So, derailment builds up slowly and one day goes boom. There are parallels with that regularly quoted line about bankruptcy: “How did you go bankrupt?”. “Gradually, then suddenly”.

One source in the book says to deal with your own derailment early in your career, while there is still time to recover from it. But, leaders make mistakes. The author says, “certain mistakes (by leaders), handled tactfully, willfully and humbly, are often forgivable and their leadership is salvageable”. One of the consistent themes in high profile derailment is that even after their career implosion, the leaders refuse to admit they got something wrong. Particularly, in this book, Carly Forina and Dick Fuld. But this extends to more widely known cases of derailment such as Lance Armstrong, and Jeff Skilling at Enron.


The power to see ourselves

Clearly, and most obviously, self-awareness is the key variable. As is common with positions of high power, the leader is truth-starved. Self-awareness develops through a healthy feedback loop. That is, feedback is a corrective mechanism for behaviour. It prompts us to coach ourselves and adjust. Contrary to popular belief, coachability has nothing to do with age or position. It’s free to all: all the time.

Derailment occurs when the corrective mechanism is broken and the feedback loop fails. But, powerful executives might “punish” truth-tellers. Which extinguishes the practice of truth-telling in a hurry. Thus, starving a leader of the power to see themselves honestly.


The toothpaste tube

“It can’t be overstated how much stress impacts our behaviour”, says Irwin. Stress causes us to give a full expression of our flaws. The author uses the analogy of a toothpaste tube i.e. the harder you squeeze it, the more you see what’s really inside. On the flip side of stress, continued success encourages people to keep doing what they’re doing. This leads to strengths being overused and becoming weaknesses. Likewise, situations of high stress also cause people to overuse their biggest asset i.e. when confidence turns into arrogance. Derailment is most likely to occur in stressed situations (Jeremy Clarkson), situations of high discretion or low control (Jeff Skilling), and finally when someone if really successful feels untouchable (Sepp Blatter).

In summary, what leads to derailment? Over time, lack of feedback and lack of willingness to act upon it.


This book review is number 2 of 5 of what we feel are the best books on leadership development and communication. We will be releasing the other reviews over the coming months. To be in for a chance to win your own set of the books and to get the future reviews direct to your inbox sign up today.