CHURCHILL: The Character of Leadership

This entry is part 6 of 12 in the series Lead Like Churchill

Winston S. Churchill c.1891

It has sadly become a popular belief that leaders are naturally born, and Churchill, many have said, was one of them. Looking at some of the leaders around the world today, the reality happily sets in that this can’t be true, or Nurse Ratched would be calling “Medication time”[1] for all of us. “Many are called,” however, “few are chosen.”[2] Anyone can be a leader, but few are considered great. Of that select few, I am honored to say that my great-grandfather was one. But his skill as a leader was not born, it was cultivated by the influence of those around him.

Hang on, I hear some shout in objection, he was born into great privilege and had much more opportunity than the average Joe. True, I can’t deny his class. He also had the best education that money could buy. Because of birth and wealth, he could join the ranks of the British Army as an officer in Her Majesty’s cavalry, instead of being forced to enter as a Private, with no hope of climbing ranks beyond Sergeant. However, none of this helped him win his political seat in 1900. Nor did the fact that his mother was friends with those in high political office.

Winston S. Churchill – War Correspondent for the Morning Post, South Africa
© Bettmann Corbis

When Churchill entered Parliament in 1900 he did so on his own merit, earned literally from his own ‘blood, toil, tears and sweat,’[3] while working as a war correspondent in South Africa. Over the sixty years he served in Parliament, he did so, like his father before him, at the will of the people who had elected him, and with their voice in his heart.

Caring nothing for rank, status, class or consequence, Churchill confidently spoke out, despite often seeing his words fall on stony ground, or be picked over in London society, like vultures to a corpse. ‘Every prophet has to go into the wilderness,’ he remarked in his essay on Moses, but it was his conviction that it was a necessary process, and that challenges presented opportunities ‘by which psychic dynamite is made.’[4] His faith that he was being prepared for greatness ran through his veins, and although he seemed at times in too much of a hurry, his speed was clearly dictated by the circumstances around him.

He led with humility, spoke with conviction, and forgave all who had hounded him unfairly, unreservedly. His faith in himself and the ability of the British people to defeat the despot over the Channel, was equaled only to his faith in God, and in “all the strength that God,”[5] could give him. With courage, faith and integrity, Churchill raised “the tattered flag [he] found lying on a stricken field.”[6] And despite the odds, stood in front of his people against a “monstrous tyranny, never surpassed in the dark, lamentable catalogue of human crime,”[7] and said “you do your worst, and we shall do our best.”[8]



JANUARY 18, 2017

Be among the first in Houston to learn about this exciting opportunity for personal growth, join me on January 18 at Willie G’s on Post Oak.

CHURCHILL: The 20th Century’s Greatest Leader
An overview of Sir Winston Churchill’s leadership and the
introduction to the Lead Like Churchill leadership course


“We can all learn to lead like my great-grandfather, with courage, faith and integrity”



The Most Important Time of The Year, 1941

Prime Minister Winston S. Churchill & President Franklin D. Roosevelt, enjoying dinner at the White House – Christmas, 1941

In 1941, Winston Churchill made two of the most important visits to the United States. In the August, he met with President Roosevelt in Newfoundland, and together they signed the Atlantic Charter, which formed the basis of the Allies intentions towards the aggressor after the war, and a pledge that the errors of the First World War would not be repeated. On December 7, the Japanese attacked at Pearl Harbor, and two days later Mussolini, followed by Hitler, declared war on the United States, thus securing the Allies victory.

It is 75-years since that terrible attack, and being a Brit, having the honour of living among you, I certainly agree with Great-Grandpapa’s sentiments in his 1941 Christmas message at the White House. “I spend this anniversary and festival far from my country…yet I cannot truthfully say that I feel far from home.”

President Franklin D. Roosevelt, and Prime Minister Winston S. Churchill, watch the Christmas Light ceremony at the White House, 1941

Churchill’s love for America led him to drop everything after Pearl Harbor was attacked and fly over to spend Christmas in America. His visit was the sign of solidarity that struck fear in the hearts and minds of our enemies, but a cord of hope in the homes of those united against the tyranny of Hitler and his Nazis.

“Let the children have their night of fun and laughter. Let the gifts of Father Christmas delight their play. Let us grown-ups share to the full in their unstinted pleasures before we turn again to the stern task and the formidable years that lie before us, resolved that, by our sacrifice and daring, these same children shall not be robbed of their inheritance or denied their right to live in a free and decent world.

And so, in God’s mercy, a happy Christmas to you all.”




“…unlike anything seen before.”

Courage, Faith, Integrity

* Draws upon Churchill’s victories and defeats
* Demonstrates how great leaders were influenced by Churchill
* Doesn’t simply instruct you, but empowers you to

Lead Like Churchill




CHURCHILL: The Wisdom Behind the Throne

This entry is part 5 of 12 in the series Lead Like Churchill
Mrs. Clementine Churchill, right, laughs heartily as British Prime Minister Winston Churchill talks at Chigwell, England, during his election campain, May 27, 1945. (AP Photo)

Mrs. Clementine Churchill, right, laughs heartily as British Prime Minister Winston Churchill talks at Chigwell, England, during his election campain, May 27, 1945. (AP Photo)

Thirty-nine years ago, one of the greatest women of the Twentieth Century, Clementine Churchill, passed away and joined her husband, my great-grandfather, Winston. They had been married for over fifty years, and although on occasion tumultuous, theirs was a relationship of overwhelming love, and on Great-Grandmamma’s part, extreme patience. As author Sonia Purnell points out, Great-Grandmamma ‘proved a genius both at patching up the wreckage caused by his [Winston’s] bad decisions, and at offering good advice.’ Purnell maintains, and from my study of Churchill’s life, I agree, Clementine’s role in Great-Grandpapa’s life was so significant that without her, his ‘career would have been a washout.’[1]

How often the vital role of women, or indeed a supportive partner or spouse has been overlooked, or indeed taken for granted. While I am sure that many can claim that they became successful because of their own hard work, few can say they remained successful due to their own merits. Whether you are a successful man, or woman, can you really say that you got there alone? I certainly cannot make such a claim. Without the support of several significant people in my own life, including my mother, my sister, and indeed, my very patient wife, I would never have made it this far in life, let alone written and had published, a book. Great-Grandpapa was unable to lay claim to his success on his own strength. Apart from the credit that he gives God, in his autobiography My Early Life, Churchill’s early career both as an officer in the British Army, and a politician from 1900, would not have been possible without the support and intervention of his American mother, Jennie. His later career success also required finesse, something his personality seriously lacked. However, wisely, Churchill deferred to Clementine, who proved on many occasions that she was very capable of fighting his corner without antagonizing his opposition, or his leaders. Following the Dardanelles disaster, it was my great-grandmother who, according to Sonia Purnell, ‘encouraged him to go to the Front,’ believing it would be good for his image. While Churchill was away serving in France, Clementine was busy ‘running nine enormous workers’ canteens.’[2] Although not necessarily a calculated political move, it certainly didn’t hurt with improving Churchill’s reputation as people realised that Mrs. Churchill, like her husband, didn’t see herself as high and mighty, but indeed equal to all, and as ready as any to roll her sleeves up, and get dirty for the boys on the Front.

Leadership is not conducted alone, and wise leaders acknowledge and respect those who helped them to the top, and never look down in-pride from above. Great-Grandpapa himself credited Great-Grandmamma with great wisdom, describing her as ‘his “sagacious military pussycat”.’[3]

This is only to give you my fondest love and kisses a hundred times repeated…I have found it quite lonely & will rejoice to see us joined together in gaiety and love.

Yours ever & always,




CHURCHILL: The Courage to Listen 

This entry is part 4 of 12 in the series Lead Like Churchill

Courage is what it takes to stand up and speak; courage is also what it takes to sit down and listen.

Often attributed to Great-Grandpapa, but in-fact, according to Richard Langworth, unattributed; but the sentiment is right, whether Churchill spoke it or not.


The Churchill’s on The Thames (c.1940)

During the 1930s, groans would be heard in the House of Commons when Churchill rose to speak. His warnings that Hitler was a problem we could not afford to underestimate were sadly ignored. But with courage, despite colleagues on both sides of the House jeering at him and shouting for him to sit-down, Great-Grandpapa remained resolute.

Churchill’s goal was clear from the earliest moments in 1933; he intended to ensure that Britain rearmed to avoid a war, the horror of which he feared would be matched, if not outdone, by the War of 1914-1918.

Great-Grandpapa proved his courage was made of metal when he stood and spoke over the unruly House of Commons, however, it was not until he became Prime Minister he proved that, although ‘always ready to learn,’[1] and not always happy to be taught, he could rise to the occasion, and, as a leader, listen to advice.  Shortly after becoming Prime Minister, Great-Grandmama wrote to Churchill, concerned at a complaint she had received on how he was handling the pressures of his office, and the war:

‘I must confess that I have noticed a deterioration in your manner; & you are not so kind as you used to be,’ Clementine wrote, ‘with this terrific power you must combine urbanity, kindness and if possible Olympic calm…I cannot bear that those who serve the Country & yourself should not love you as well as admire and respect you.’[2]

Great-Grandpapa’s attitude changed overnight. Although still occasionally overbearing, the cruelty disappeared completely, and as a result, colleagues he worked with remembered him fondly and considered him a great hero. I personally feel that his late secretary, Grace Hamblin, summed-up the sentiment best. In a letter penned to Clementine Churchill, following the funeral in London, Grace wrote:

‘I pondered on what had made this dynamic but gentle character so beloved and respected—and such a wonderful person to work for. I think one found first of all that there was courage. He had no fear of anything, moral or physical. There was sincerity, truth and integrity, for he couldn’t knowingly deceive a cabinet minister or a bricklayer or a secretary. There was forgiveness, warmth, affection, loyalty and, perhaps most important of all in the demanding life we all lived, there was humour, which he had in abundance….’[3]

Leading with courage is one of the most important qualities of leadership because, ‘as it has been said…Courage is rightly esteemed the first of human qualities because…it is the quality which guarantees all others.’[4]

Note from the author: This blog post represent information based upon Jonathan’s Churchillian leadership course,
LEAD LIKE CHURCHILL: Courage, Faith, Integrity.
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