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Winston Churchill, CEO: 25 Lessons for Bold Business Leaders

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Following his BusinessWeek bestsellers Elizabeth I, CE O and Patton on Leadership comes a new and perfect subject for Alan Axelrod’s innovative Winston Churchill, the quintessential leader of the 20th century. Churchill skillfully converted crisis into victory, making the boldest of visions seem attainable; even though he sometimes failed audaciously, he embraced his errors and used them to become stronger. Axelrod looks at this much-studied figure in a way nobody has he explores 25 key facets of Churchill’s leadership style and decision-making from his early years as a junior cavalry officer and journalist to his role throughout WWII and demonstrates how he was able to overcome near-impossible obstacles. Fluidly and engagingly written, each lesson is enlivened with a vivid vignette from Churchill’s life. As always, Axelrod’s penetrating analysis will instruct, inspire, and encourage those who lead business enterprises, large and small.

276 pages, Hardcover

First published May 1, 2009

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131 people want to read

About the author

Alan Axelrod

176 books53 followers
Alan Axelrod, Ph.D., is a prolific author of history, business and management books. As of October 2018, he had written more than 150 books, as noted in an online introduction by Lynn Ware Peek before an interview with Axelrod on the National Public Radio station KPCW. Axelrod resides in Atlanta, Georgia.

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5 stars
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Displaying 1 - 16 of 16 reviews
Profile Image for Egor.
19 reviews
July 27, 2018
In my opinion, the book does a good job of analyzing why Winston Churchill was a successful leader and it shows that in fact, the principles he used can be applied to everything in your everyday life. The book gives many examples to prove the points, which does give it additional credibility.

As with any book that offers advice on interpersonal relationships and business, it's not the end-all, be-all, but it definitely provides a nice foundation to build you skills on.
105 reviews
May 29, 2017
While I enjoyed reading further into the events of Winston Churchill's life, I believe my expectations had been wrongly set on being given a more thoughtful evaluation of those events and how they might apply to business leaders today. I felt the author's interruptions to Churchill's prose were unnecessary and distracting. Overall I would not recommend this book to others in search of a true application of Churchill's life to those in the business world today.
Profile Image for Katyа Zubko.
63 reviews
April 29, 2025
This book will be interesting for anyone who wants to better understand what kind of leader Winston Churchill was. It's an easy read. The author shows Churchill not just as a politician, but as a true leader you can really learn from.
Profile Image for Steven.
Author 32 books9 followers
October 14, 2016
This is a good book if you wish to be a better leader. Churchill, of course, was the right man for his time and his country. You might prove to be the right person at the right time for your organization, and a little preparation (through reading this book) wouldn't hurt. The 25 lessons here are useful and actionable.

The book suffers a bit from repetition. Also, it's nine tenths biography, and one tenth relating the biographical parts to useful CEO advice. However, the biography is well written, and gave me a great picture of the great man.
154 reviews4 followers
April 11, 2011
Winston Churchill has long been considered a symbol of fearlessness and bravery, especially during a time of grave danger to world peace.
He was a prominent English statesman who shrewdly turned any defeat into opportunity and boldly demonstrated self-confidence and leadership.
Axelrod astutely utilizes a variety of stories and events of this British bulldog's life and concisely presents 25 lessons to learn, in order to excel as a leader in a boardroom.
He imparts his insights with the help of vivid quotes and historical tales.

Since 25 lessons seem too tedious to review, I have picked my favourite from this book:

1) Get down in the trenches and get your hands dirty,: showing yourself in the front lines boosts morale by everyone by demonstrating that you are in touch with your enterprise.

2) Never allow yourself to be confined in the prison of someone else's ideas. Despite any risk, taking timely action may well allow you to define yourself before others do it for you.

3) Win Your Authority Every Day. Leaders require followers and ensure that those who do follow, do so voluntarily. Make followership a matter of choice.

4) Negotiate from Strength. Best time to enter key negotiations is when things are going well; when you are strong and have the greatest range of options. It's hard to be persuasive when your back's up against the wall. For instance, Mark Twain once griped that banks would lend money only if you could prove you didn't need it.

5) Greet Hardship as Opportunity. To manage information is to discover and open the potential for profit in any event. Opportunity often requires an advocate to identify and promote it.

6) Gather Good Partners: Take every opportunity to demonstrate your commitment to your allies and your partners.

And some of my favourite Churchill sayings from this book:

"Success is the ability to go from one loss to another with no loss of enthusiasm"

"I cannot forecast to you the action of Russia. It is a riddle wrapped in a mystery inside an enigma"

"A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty"


Profile Image for Jared Pyatt.
20 reviews6 followers
August 16, 2010
This is a good book. Having always been interested in Churchill, this work on his leadership lessons peaked my interest. While most of us aren't convincing others about why or why not we should be going into war(s), Churchill was a master at providing prospective, priorities and learning from failure. Churchill was a winner and his style of leadership can be effective in all positions and organizations in the 21st century. In the end, traits such as: honesty, relationship building, communication and conviction are still admirable in a leader.

This is a great book for those interested in learning more about Winston Churchill and maximizing their leadership potential.
Profile Image for Othón A. León.
100 reviews3 followers
November 12, 2012
I highly recommend this book. Full of wisdom... political, war, peace, business wisdom... all the things that Sir Winston Spencer Churchill standed for are included here and reinterpreted in what I would say is more than business adaptation. Alan Axelrod wanted that, yes, but in his effort he achieved a humanistic approach to that of a theory of organizations. Business are made from people to people, therefore, everything is personal in business. From Winston's young days to old Winston's last period, this is a fascinating recount of his leadership lessons and managerial experiences.
Profile Image for Robert McKeehan.
16 reviews24 followers
July 31, 2012
As commanding of a leader that Churchill was, he deserves a better treatment of his leadership principles and practices than is found in this book. Having read several biographies on Churchill, this book lacks depth and texture. It's strength is the identification of 25 so-called leadership principles from Churchill's life and legacy. It's weakness is that it explains many of these principles tediously and repetitively.
Profile Image for Effendy Yahaya.
125 reviews2 followers
January 1, 2015
I love on how Alan wrote about Sir Winston Churchill and narrated it in a good structure of lesson learnt and directly relate it to business. Patience and persistent is what I would carry on my next venture in 2015. I have bought Gandhi and Napolean, I can't wait to start on it. V for victory!
3 reviews4 followers
Read
September 14, 2010

my 5 weeks old daughter who I ma reading it to since I got no time whatsoever thinks it` s the most boring book in the world

PS
I like it.
Profile Image for Mohit Rastogi.
4 reviews
Read
May 15, 2016
Very captivating book. Written in a fluid manner , the fast pace of the book keeps interest alive and flipping of pages one after the other.
Displaying 1 - 16 of 16 reviews

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