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I’ve just finished reading Andrew Robert’s magisterial biography of Winston Churchill, a 982-page account of a life so astonishing I had to remind myself repeatedly it wasn’t fiction, but true history. There’s so much to learn from the story of this remarkable, complex man – especially for those of us burdened/blessed with the privilege of leadership. Here are four lessons I am reflecting on, summarized in four broad headings.


Winston Churchill grew up idolizing a distant, absent and profoundly neglectful father, one he could never seem to win the approval of. In the end, despite some early successes, Randolph Churchill failed not only as a father, but as a politician, and died at a relatively young age with thwarted ambition. His son’s life, leadership, character traits, and lofty ambitions were shaped more by his absence than anything else – and his driving desire to vindicate his father’s memory and in some way, win his haunting approval.

I am reminded that who we are as both people and leaders is influenced in large part by our family of origin, and to think otherwise, is naïve. Self-awareness, including knowledge of the family characteristics, history and dynamics that have shaped us (the good and the bad), is a critical attribute of any emotionally intelligent leader. (I am so grateful for my incredible family, and my wonderful dad, whose influence blesses me still)


A prolific author, celebrated journalist and eventual winner of the Nobel Prize for Literature, Churchill was perhaps the 20th centuries most revered orator. During the dark days of World War 2, when defeat seemed likely, the American journalist Edward R. Murrow said of his speeches that roused a cowering nation and empire, ‘he mobilized the English language and sent it into battle.’

Undoubtedly this was a skill he in part inherited from his father. But it was also one he cultivated with diligence and discipline from a very young age. A voracious reader, and blessed with an incredible ability to memorise, he knew that to realise his ambitions required the mastery of words. In an essay he wrote as a 23-year-old, he said:

Of all the talents bestowed upon men, none is so precious as the gift of oratory.   He who enjoys it wields a power more durable than that of a great king.   He is an independent force in the world.   Abandoned by his party, betrayed by his friends, stripped of his offices, whoever can command this power is still formidable. (Winston Churchill, ‘The Scaffolding of Rhetoric’, 1897)

Churchill’s speeches, witticisms, articles and books were key to the longevity and effectiveness of his leadership. His words were always carefully crafted and well-rehearsed.

Borrowing from a saying of Martin Luther King Jr, like a thermostat, leaders set the temperature of their team. Well chosen words, spoken or written, can inspire, challenge and move a team to be and achieve more than they ever could or would otherwise. What I say and write as a leader matters a lot. Making the time to shape messages that not only inform, but move people to collective action, is critical. To not would be an abject failure as a leader.


Winston Churchill collected and cultivated wildly divergent circles of friends across his life. Political and ideological differences didn’t get in the way, nor even war. Jan Smuts, Churchill’s one-time Boer War enemy, would become one of his closest friends.

‘Blackballed’ by one of London’s establishment clubs in the early 20th century, Churchill helped establish ‘The Other Club’, a regular and wall-watered dinner meeting that ignored normal tribal allegiances, which was attended by similar mavericks from across the political spectrum, and included authors, scientists, businessmen and politicians.

At times Churchill experienced immeasurable leadership loneliness, especially in the darkest days of the war, and after the many political setbacks he experienced, some self-inflicted. But this was tempered by the relational capital he had developed over many years – the ‘happy few’ who always had his back and who often filled his emotional cup. And who, when necessary, challenged him.

Leadership is not a solo endeavor. Only those leaders who have around them a ‘happy few’ will thrive, let alone survive.


An admirer of his friend TE Lawrence (Lawrence of Arabia), Churchill’s life reads like a barely believable ‘boys own’ adventure. As a soldier he was constantly in danger, shot at, captured and imprisoned, an escapee and a survivor of the horrors of the trenches of the Western Front. He was also a reckless pilot who survived a plane crash, and a skilled horseman who suffered many injuries.

Perhaps even more, Churchill endured many political, military, financial and personal setbacks, including a disastrous term as Chancellor of the Exchequer and conceiving and pushing for the tragic Dardanelles (Gallipoli) campaign of WW1. There were so many others mistakes and missteps, too many to recount. Perhaps the most admirable of all his many qualities, it is Churchill’s resilience that I admire the most. Just one of these setbacks would be enough for most to turn away from every aspiring to any significant leadership in the future. Not so for Winston Churchill. He never failed to learn and always failed forward.  It was because of this, that, when his nation and the world needed him and his unique skillset the most, this most remarkable of leaders was ready and more than able to take up the call.

Once, after retreating from another significant defeat in parliament, Churchill took up his role as an officer leading troops in the Western Front trenches. From the mud and muck and terror of those times, he wrote to his wife, ‘as one’s fortunes are reduced one’s spirit must expand to fill the void.’ (20 December 2015) Churchill’s spirit never failed to expand to fill the void created by external circumstances. Resilience born from his optimism and self-belief not only served him well, but indeed the whole world.

The hardest person anyone leads is themselves. Churchill’s example reminds me that, ultimately, only I can take responsibility for, and can feed my own relational, emotional and mental health. I cannot give others what I do not have. I cannot lead from an empty cup. I cannot lead people to a well I’m not drinking from myself.

One Comment

  • I do trust all the ideas youve presented in your post They are really convincing and will definitely work Nonetheless the posts are too short for newbies May just you please lengthen them a bit from next time Thank you for the post

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