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Churchill on Leadership: Executive Success in the Face of Adversity

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Success often depends on the strength of a single leadership. Winston Churchill is universally recognized as one of the 20th century's great political leaders and his words ring just as true in the world of commerce. A wise, witty, and inspiring leader, Churchill ran Great Britain like a great corporation.

"Perhaps the finest book on practical leadership ever written." — Brian Tracy

Churchill on Leadership demonstrates that the principles that guided Churchill ably translate to private industry today. Author Steven F. Hayward gives strong evidence that, if you remove Churchill from his political context, he would have the resume to be among the great business leaders of any age.
• was a financier (as chancellor of the Exechequer) and labor negotiator (as home secretary)
• managed a large transportation network (as head of the British Navy) and far-flung property holdings (as colonial secretary)
• persevered through bankruptcies and other financial disasters
• conceived and introduced innovative new products over the opposition of his colleagues, and reorganized major production operations in the midst of crisis.
With wit and insight, Hayward reveals Churchill's secrets for business success from assembling and inspiring a first-rate team to preparing a wise budget, from communicating a vision to structuring effective meetings, from acting decisively to rebounding from a failure. Laced with epochal events from the historical stage, enlivened with stimulating speculation, and leavened with wit, Churchill on Leadership is both an enjoyable read and a thought-provoking lesson on leadership.


From the Trade Paperback edition.

224 pages, Hardcover

First published April 30, 1997

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Steven F. Hayward

24 books22 followers

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5 stars
64 (28%)
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55 (24%)
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11 (4%)
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Displaying 1 - 15 of 15 reviews
Profile Image for Gary.
61 reviews11 followers
November 16, 2008
Good book. There are so many things that we don't learn in school that should be taught. Leadership of course, but even things in history that get glazed over. This book has some good things to know about a great leader and a great man.
Profile Image for Chandler Collins.
499 reviews
July 16, 2024
I found this book very similar in style and format to Donald Philips's "Lincoln on Leadership." Hayward describes well Winston Churchill's work as a political and military leader and draws out (sometimes reads in?) leadership principles from his character and leadership style. The end of each chapter also contains bullet-points of the leadership principles that Hayward explicated in the chapter, and Churchill's quotes or "maxims" that accompany the leadership principles. These sections make the book a great reference work! I particularly enjoyed the chapter on Churchill's rhetoric and communication, as well as Hayward's early emphasis on Churchill's historical imagination and the significance of history for leadership. I also enjoyed learning about Churchill's diverse interests and hobbies as he contended that everyone should have 2-3 hobbies. Churchill was a painter, a writer of very thorough history texts, and one who enjoyed afternoon naps. He kept a rigorous but remarkable schedule throughout his career. There is also an appendix that is a stricter biography on Churchill's executive career. Hayward also explains the structure of British government in this appendix that will interest any anglophile (such as myself).

My main critique with this work takes significant space to explain but it is not that serious of an issue with the book. The problem is Hayward's treatment of Churchill as a completely faultless leader. In Hayward's eyes, Churchill could never do any wrong. Hayward often mentions criticisms raised against Churchill's leadership style but quickly dismisses them as exaggerations or misunderstandings. At one point, Hayward even refers to Churchill being a "disgraced leader" in the eyes of the British people, but there is no explanation in the book as to why they viewed him that way. In Hayward's effort to paint Churchill as a faultless leader, Hayward even develops certain inconsistencies in his interpretation of Churchill's leadership style. For example, Hayward explains how Churchill was a man who rightfully claimed responsibility for all of his decisions and how Churchill would not blameshift or throw anyone under the bus for failed strategies. Yet, when Hayward describes the Dardanelles affair (perhaps the biggest nightmare of Churchill's career), Hayward blames everyone but Churchill for the failure of the plan. I thought this attempt to clear Churchill from every criticism was interesting, but I am not well-versed in the life of Churchill, so I do not know if any of the criticisms hold any water.

Still, while many contemporary leadership books are white noise or do not add anything to the field of study, I find these books on the leadership styles of historical leaders to be very illuminating and refreshing from a leadership and historical perspective. Hayward's writing style is extremely clear even if it is a little hagiographical. I would highly recommend this book!
Profile Image for Bryce Pinder.
329 reviews3 followers
February 11, 2019
(B-school)
Pros - Concise look at the positive areas of Churchill's leadership, with many examples from his life and plenty of great quotes. Leadership principles that stood out to me:
- Premium on action
- No fear of being wrong, willing to accept responsibility for failure
- Build an organization from the top down, not the bottom up
- Taking ownership, stepping in when something needs to get done

Cons - Not a biography so you don't learn much about his actual life, Hayward is pretty imposing with his interpretation and application of Churchill's leadership principles, and there is no focus on Churchill's faults as a leader (all faults are defended or explained away).

Favorite Churchill quotes:
If we look back on our past life we shall see that one of its most unusual experiences is that we have been helped by our mistakes and injured by our most sagacious decisions.

Success is going from failure to failure without loss of enthusiasm.

Ponder, and then act.

In the course of my life I have often had to eat my words, and I must confess that I have always found it a wholesome diet.
Profile Image for False.
2,437 reviews10 followers
April 25, 2022
As we all know too well, in the flow of flotsam from academe, there is seldom material that is both readable and edifying. Often neither quality is present. This book, Churchill on Leadership, scores high in both categories. Hayward's obvious in depth knowledge of Churchill and his times enabled him to organize the vast storehouse of material available into a useful and unique way of teaching the leadership principles Churchill personified. God knows the lack of leadership today evidences the extreme need for what Hayward has wrought. And, I might add, Churchill was highly quotable. I truly enjoyed this book and plan on reading more of Churchill's own writings.
5 reviews
September 9, 2020
Doesn’t quite succeed

This book combines history with biography and leadership and doesn’t go far enough in any of these areas. It reads more like a senior thesis...first let me tell you about Churchill’s thoughts and actions during this period of history then let me shoehorn that into a lesson on leadership.

There are undoubtedly many leadership lessons to learn from Churchill’s life. This book is a little clunky in the way it shares them.
Profile Image for Austin Odom.
5 reviews
April 14, 2020
The book organized the traits of what it takes to be a good leader from the perspective of Winston Churchill. It talks about how to deal with failures, organizational management, and personality traits that Churchill exemplified on his road to success. An excellent read.
Profile Image for Rick Davis.
Author 1 book3 followers
October 25, 2020
Although this book was published in 1997, the subtitle is certainly applicable today. Hayward did a good job providing an overview of Churchill's career and life, and applying practical leadership lessons.
Profile Image for Colby Holloway.
364 reviews19 followers
June 29, 2019
Surprisingly interesting book on a man who said lots of fun little pithy things! My only complaint is that the author used the same anecdotes throughout the book.
427 reviews
June 13, 2022
While the attempt is admirable, this is an example of placing a round peg in a square hole.
Profile Image for Peter Jones.
645 reviews132 followers
August 24, 2016
A solid book, but not as good as the similar book on Robert E. Lee. What is most amazing about Churchill is his persistence. Perhaps no political leader who has had a great impact was faced with so many situations where it was assumed his career was dead. Over and over again Churchill rose from the ashes. It is worth remembering that he did not just see the looming Nazi threat he went on record as seeing it, thus again putting his career at risk if his alarms proved false.

Finally, his eulogy at Neville Chamberlain's funeral is good example of his ability to speak truly, yet kindly of people with whom he differed. Chamberlain and Churchill were political adversaries, but when Chamberlain died and Churchill gave the eulogy he did not flatter Chamberlain, but nor did he destroy him. It is a good example of how Churchill did not hold a grudge.
Profile Image for Shivam Agarwal.
25 reviews11 followers
November 2, 2014
Learnt a lot about a person whose determination affected many events. I don't know much about the world history and have just started exploring it. This book taught me that a person's character and life is heavily influenced by external factors and interactions with other people. But still it depends a lot on the path one takes. One cannot say that positions held by W. Churchill were "accidental", rather he built himself and then contributed back.
Profile Image for Olivia.
7 reviews
Want to read
January 24, 2011
I'm so all over the place with books this time around. I just borrowed this from someone at work and am reading it little by little. We'll see what Churchill has to teach me :)
Profile Image for Jason Jay.
20 reviews
March 11, 2016
Great read!. Interesting, motivational, and informative. Good balance of story and principle. I really enjoyed learning about Churchill as well as his approach to leadership.
Profile Image for Collette.
429 reviews
August 23, 2015
I really enjoyed learning about Churchill and his leadership style. Such a fascinating man.
Displaying 1 - 15 of 15 reviews

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