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Derailed: Five Lessons Learned from Catastrophic Failures of Leadership

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Vibrant stories of well-known execs who failed spectacularly as senior executives of major corporations. Read about and learn from these colorful and entertaining derailers who misread the symptoms of their own doom and failed to take the corrective actions needed to sustain their viability as leaders.

217 pages, Hardcover

First published October 7, 2009

About the author

Tim Irwin

18 books4 followers

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5 stars
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66 (44%)
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Displaying 1 - 30 of 32 reviews
Profile Image for Thomas Freeman.
61 reviews7 followers
December 15, 2009
Derailed: Five Lessons Learned from Catastrophic Failures of Leadership by Tim Irwin

I found this book to be overly simplistic and generalized. Tim took the downfall of 6 different corporate leaders and identified five key character deficiencies he believes contributed. He breaks character in to four key areas: authenticity, self-management, humility, and courage. I do believe the deficiencies were clearly there but I also believe that the derailments may have been more complex than Tim describes. Tim is attempting to present this material in the same form as “From Good to Great”. However, he simply doesn’t have the same amount of research and connections between the CEO train wrecks. His dogmatic assertions are not based on scientific study but rather on an intuitive surface level.

That being said, there is no doubt that these CEO’s would have been better leaders if they had developed these character qualities. Tim does a good job of explaining each quality and showing how they could have a positive impact on business leaders today. I particularly appreciated the way he presented the quality of courage and how it has an impact on the leadership provided. Tim asserts that derailment is a process and I believe we would all agree. However, I’m not sure that it will always happen in the same order.

After profiling the 6 leaders, identifying character deficiencies and showing the downward process they follow, Tim gives two chapters to explain how we can avoid a similar downfall. He does a fine job but I believe that much more could have been said.

I probably would not recommend this book. I found the book simplistic and boring. I believe that you could find better books on leadership qualities and leadership deficiencies than “Derailed”.
Profile Image for Norm Konzelman.
126 reviews4 followers
May 28, 2014
There are six or seven brief summaries of the character of famous captains of industry, and the decisions they made that caused them to self-destruct in the first third of the book. By the time I got to the last example I began to despair a little thinking, is this book going to go anywhere? After all, you can see the same thing anywhere every day in the lives of people. But then, Wham! The tone of the book changed, and went directly to character. Character that makes a success, contrasting that with the character/decisions that would cause failure.
The last third was the good habits to acquire, and how to obtain them.
It was very inspiring for me personally, opening up weaknesses within me, and ideals I would like to aspire to. What shone through during the whole time reading was how God has been teaching me these things over years in His word and through my Pastor.
What is taught takes so many forms. Just as there are so many people, all different yet the same in the issues they have and face.
It is simplistic to say and don't miss this book because of it, but you could say it is 'pride versus humility'.
I am very pleased I was able to enjoy this book, and a little of the author.
Profile Image for Katt Hansen.
3,700 reviews104 followers
October 16, 2012
Fascinating how people in high position go wrong. We watch them fall, almost gleefully sometimes, thinking "They got what they deserved." The actions these powerful men and women take seem SO outrageous, we can't understand how they came to have so much power to begin with.

But then we realize that it's not just them, it's us. Maybe we aren't buy $8,000 shower curtains but the little indulgences, the small lies, the actions we take to get ahead show that those same character traits are things we need to be aware of. These are the things that can lead to huge derailments down the road.

This book was interesting, the first half being one horror story after another with a little bit of analysis of what led to the fall. But then we get into the meat of things, the exposure of these own traits in ourselves, and a look at what we can do to keep them from derailing us.

It's an interesting concept but by far too negative for me. We're looking at failure in depth, and how we can learn from failure. I felt like there were an awful lot of 'don't do this' but not enough emphasis on positive actions we can take as leaders (or would-be leaders). I came away unsettled and a little overwhelmed and unhappy overall.

This won't be one I'll be picking up again though there was some good information here. Not one I'd really recommend unless this style of book works for you.

*** I received this book free from a blog giveaway with a request for an honest review. ***
Profile Image for Tunde Disu.
3 reviews
January 26, 2016
One of the best books on leadership lessons ever! The detailed description of each character highlighted in the book, their background, road to stardom, their highest peak of power and influence, their flaws and errors and the proposed solutions to avoid such makes this a once-in-a-lifetime lesson book.

Highly recommended for leaders, those around them and those aspiring to become leaders.
Profile Image for Gina Herald.
77 reviews3 followers
April 19, 2011
Unfortunate story about some incredibly talented people who let pride, greed and self-importance get in the way of solid leadership.
Profile Image for Richard Angelus.
180 reviews2 followers
October 20, 2019
Derailment means "off the rails." To be a derailed leader means to fall short of inner character that results in outer disaster. No one is immune from the derailment. I've been to the dark valley of my character flaw. I went to prison because of it. A minor crime, I assure you, but a serious lack of character issue. WHY and HOW did derailment happen? 

Read my (somewhat) Book Review of Tim Irwin's Derailed: Five Lessons Learned from Catastrophic Failures of Leadership (2009), CLICK HERE: https://www.richardangelus.me/2019/10...



Profile Image for Rye Bailey.
41 reviews1 follower
April 30, 2019
The anecdotes on real-world leaders who have derailed setup this book greatly. Dr. Irwin takes principles from their negative examples and gives practical ways to implement roadblocks into our personal and professional lives so that we don't make the same mistakes and end up derailed. I highly recommend this book for professional circles. It was a quick and easy read, but packed with valuable insight.
Profile Image for Amish.
17 reviews
May 22, 2020
Brilliant read, case studies with great examples of leadership failures. If you want to understand your own performance as leaders you would do well to evaluate yourself against the spider chart of competencies this book highlights. There is a certain simplicity to the ethos which only makes it that much more accessible to the reader, and fundamentally clear.
Profile Image for Darren Sapp.
Author 10 books20 followers
February 1, 2022
We have so many books about leaders or soared but few on those who sank. This book chooses six, tells us why, and offers a way for all of us to avoid those pitfalls.
8 reviews
February 15, 2010
Applying the term derailed because of the train wreck September 2008 in California and the fact that it was due to human error Tim Irwin proceeds to give 6 illustrations of leaders who have derailed their careers in spite of the fact they were talented and had a prior history of success.

We all have the opportunity to be derailed in life. Tim’s purpose of this book is not about the six profiled leaders, but instead is to help define what derailment is and to hopefully help us stay on track.

Derailment is a process and usually in slow motion and the derailing leader usually believes he is right and must stay the course, despite any warnings that may say otherwise.

The larger portion of the book is on providing us with the warning signals and helping us to hopefully avert them and to stay the course for the long haul. He helps us evaluate our character, authenticity, humility, and courage. He says that our brand is not what we say it is but is what others say it is, and there are early warning signs we should watch for.

“great leaders channel their ambition toward building their organization rather than personal aggrandizement.”

They realize “Most work in the organization is done by teams…when someone takes excess credit, he will ‘get cut from the herd pretty fast.’”

My only thought is that sometimes there are derailment casualties of a derailing leader frantically trying to hold on. However, this book will give us insight into our personal character and responsibility and will prove invaluable to any person who will read it and apply its principles.
Profile Image for Andrew Murch.
49 reviews16 followers
January 11, 2016
Life's greatest lessons usually come to us through failures. Experience can be a harsh teacher. Often we don't realize critical areas we are falling short until we get derailed. In the aftermath, if we're fortunate to look at ourselves objectively, we can grow and move on with the added benefit of not making the same mistakes the next time around. I've seen this play out in my own life and in numerous other lives as it relates to job performance, relationships, and any other number of critical areas.

Tim Irwin's book 'Derailed' offers us the opportunity to learn from failures not our own. In it he profiles 5 top-shelf CEO's who derailed badly, crashing and burning on the big stage of Fortune-500 business. After analyzing the situations post-mortem, he offers some concluding chapters intended to give the reader a road map to effective leadership. I see these final chapters as 'guard-rails' which help us stay on track. Although the stakes may not seem nearly as high for many of the readers of this book, the lessons applied to individual lives and contexts have the potential to keep anyone on track.

This is a great read for any leader or manager. If you've read Jim Collins' book 'Good to Great,' Irwin's book is an interesting look at the other side of the coin. Also, if you're a fan of Patrick Lencioni's books (which I am), you'll enjoy Irwin's style. If you have any interest in business, it's especially engaging.
Profile Image for Ellen Christian.
229 reviews236 followers
November 20, 2009
Derailed chronicles the careers of six CEO’s in the business world. Each of these CEO’s had a career that many would envy; well paid and in control. They also each had one thing in common. They all failed at their careers due to a lack of leadership skills and character.

Derailed gives the reader a look into each person’s career and allows them to see how they failed and what lessons can be learned from their failures. A few of the CEO’s he describes include Dick Fuld, former CEO of Lehman Brothers, and Durk Jager, former CEO of Proctor & Gamble.

Tim Irwin explains what the five stages of derailment are and how we can avoid them in our personal lives by recognizing the attitudes and behaviors that lead us there. This book is ideal for anyone who holds a leadership position in their lives. You don’t have to be a leader in a business capacity, these ideas can easily be used by teachers, pastors or youth group leaders.
Profile Image for Jeremy.
789 reviews21 followers
December 13, 2011
This book was disappointing. There were some Collins-esque profiles of CEO's, but in my mind they were overly brief and did not communicate many transferrable principles. I found the book to be a bit disjointed, and the calls to action to be overly trite and vague (like "never, ever be arrogant") I don't think anyone ever makes a conscious decision to be arrogant, so this tip is irrelevant.

The big idea of this book is that character is the most important characteristic of a leader. If you want to dig in on that idea, I would recommend reading Leadership and Self-Deception, Integrity, Becoming a Person of Influence, or the Bible.
Profile Image for Jeff.
238 reviews45 followers
January 19, 2010
Tim's book is a wake-up call. He profiles leaders who have derailed and then walks us through the cause of it. The derailments of these leaders are tied to a lack of or failure of one of these four critical qualities:
1. Authenticity.
2. Self-management.
3. Humility.
4. Courage.

This would be a good book for your team or co-workers to read through together. There is a free online assessment as well as part of the book.
Profile Image for Jeremy Copeland.
79 reviews1 follower
February 18, 2010
A good book for anyone in leadership. Especially those early on in leadership - the point is to avoid the things the leaders in this book failed to avoid. There were lots of nuggets in here, but the main thing that stood out to me was to avoid pride and be willing to listen to other people. Leaders that fail to listen end up alienating themselves and losing their own voice in the process.
Profile Image for Adam Shields.
1,750 reviews112 followers
August 19, 2011
Short review: Decent book on character. The audiobook isn't narrated all that well. But the particular subjects of the book felt like they were chosen and presented in a way that did not really tell the whole story.

The longer review is on my blog at http://bookwi.se/derailed-five-lesson...
Profile Image for Pathway Midland.
142 reviews6 followers
May 8, 2012
Derailed is one of the better business books I have read in a while. I have to admit it took me a long time to pick it up but once I did I couldn't put it down. The 2nd half of the book was probably the most helpful with pointing out the things we do that are keeping us from reaching our potential.

--Jeanette
Profile Image for Glenn Williams.
57 reviews
August 6, 2010
Great book. Must read for all leaders and potential leaders in business, the not-for-profit world, or ministry. It takes a good look at the key facets of leadership and if they do not exist, how you can derail any organization.
Profile Image for Matthew.
312 reviews6 followers
March 5, 2011
While this wasn't amazing all the way through and maybe not even worth 4 stars, it was a much needed reminder for me and my staff. If you are a leader and you don't have character, you are headed for an inevitable derailment.
Profile Image for Thomas Kinsfather.
254 reviews4 followers
July 21, 2010
The lesson: Don't be a selfish jerk.

Irwin chronicles the fall of 6 CEOs whose character falls trumpets their competency. A good read leaders.
Profile Image for Michael Hearn.
2 reviews4 followers
August 7, 2010
Amazing insight and principles to implement in each leaders life...warning flags to watch out for
Profile Image for Gina Mcclain.
16 reviews12 followers
December 30, 2010
Interesting read. I was familiar with a few of the case studies but not all. I found the assessments subjective. Still lots to learn and benefit from as a leader.
Profile Image for Rat Barrel.
42 reviews3 followers
December 22, 2011
For those looking to better understand dysfunctional leadership patterns, this book is a must-read.
Profile Image for Theqs13 Halim.
8 reviews
January 10, 2012
No man is an island,
Entire of itself.
Every man is a piece of the continent,
A part of the main....
-John Donne-
Profile Image for Doug Allen.
29 reviews1 follower
January 2, 2014
Good real-world examples of management self-awareness (and lack thereof).
Profile Image for Brandon Allen.
44 reviews2 followers
July 14, 2015
Great book on leadership examples of failure. I loved the principles for leadership success in the book. Definitely recommend for leaders.
Displaying 1 - 30 of 32 reviews

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