Lessons from The Last Lion - A Book on Winston Churchill

I finally finished the "Last Lion - Winston Spencer Churchill, Defender of the Realm, 1940 - 1965" by William Manchester and Paul Reid, and I'm finally putting my thoughts together regarding the book and the lessons learned. Now most of my peers would wonder why a thousand-page tome about a British Prime Minister half a century ago would be relevant to our work today. Having trudged through the book, I can reassure you that its lessons are perhaps as relevant and powerful if not more so than any business books out there. In case you don't have the time or the patience to read it, I suggest watching Into the Storm, a 2009 movie that basically captures the essence of Churchill's story during the war. Below is my crude attempt to summarize some of the lessons I've found useful in my capacity as a tech CEO (the order of which has no chronological importance. I just want to blurt out my thoughts).

Details, details, details

Often I struggle with the level of operational detail that I'm supposed to be concerned with. Should I delegate and not look over people's shoulders? To what extend should I concern myself with the details of the product? What if the color / design is off and it really bugs me? But on the other hand, I can't possibly check everything. My team might even think that I don't trust them. Having read Steve Jobs by Walter Isaacson and The Last Lion, I found remarkable similarities between the two leaders - both were known to be obsessed with details. In fact, Churchill cared about the details of war-planning to the extent that he appointed "himself his own minister of defense, thereby assuring that he himself working through Major General Ismay, would manage the Chiefs of Staff, conducting the war day by day, even hour by hour." War against Hitler was Churchill's mandate and enterprise so he was not afraid to immerse himself in the details of day-to-day warfare. Likewise, leaders must be very hands-on and detail-oriented. My experience developing a new product with top engineers from JD also proved that although it wore me down, the attention to detail is worth it. 


"Even though large tracts of Europe and many old and famous states have fallen or may fall into the grip of the Gestapo and all the odious apparatus of Nazi rule, we shall not flag or fail…. We shall go on to the end, we shall fight in France, we shall fight on the seas and oceans, we shall fight with growing confidence and growing strength in the air, we shall defend our island, whatever the cost may be, we shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall never surrender."

- Winston Churchill, June 1940. 

In business, it is not uncommon to find challenges and opponents that are seemingly too overwhelming for us. We feel like we're punching above our weight. We feel cornered by the constant barrages and defeats, but that's precisely when we should keep fighting and exhibit an indomitable spirit. Stand firm against bullies and don't budge. Don't be afraid to stand up for what is right. Great Britain was losing almost every single major battle in the first half of World War II that the public, political, and psychological pressure on Churchill must have been unbearable. Nevertheless, he kept the public spirits up and kept on fighting. Eventually, the tides turned when the United States entered the war and the rest is history. Thor Bjorgolfsson, the Icelandic billionaire, endured a torturous partnership in an impossibly chaotic environment (Russia in the 1990s) before finally establishing a foothold as the sixth largest brewery in Russia.  This is a particularly hard lesson for me. My natural reflex in face of danger, defeats, and bullies is to run and give up. After all, it's so easy to run away. In light of that, I've decided to find a project and hunker down, hopefully to achieve something impactful. Perseverance, I think, is the ultimate barrier to entry. 


You can't always have the best team. Most of the time, we'd be lucky if we could get any team to work effectively together. It's easy for management gurus to say that we have to focus people's strengths but that's easier said than done. I can relate to Churchill's pragmatism in working with two particular individuals, Anthony Eden and Max Beaverbrook. Anthony Eden was the one who as Churchill's deputy patiently waited his turn to be the PM but is considered to be weak while Max Beaverbrook had a controversial reputation but had the execution capabilities to "deliver the goods".  

"Churchill was going to need a lot of airplanes soon, and he knew this man had the drive and the ruthlessness to get them one way or another. Beaverbrook, he told Jock Colville, was "twenty-five percent thug, fifteen percent crook and the remainder a combination of genius and real goodness of heart."

- Manchester in The Last Lion

It was a coincidence that while I was reading the book, I had on my core team two particular individuals that mirrored Eden and Beaverbrook. Surprisingly their roles were almost exactly the same as the latter on Churchill's team. Many questioned the wisdom of having them on the team but from my experience and my interpretation of Churchill's intentions, you need both the diplomatic peacemaker and the resourceful and capable lieutenant to get things done, and the eventual outcome of WWII justified Churchill's team selection. 

Other Lessons

Unless you solve the problem of supplies, you cannot win the war. Lifeline (in the form of technological breakthroughs and economic supplies) from the States was crucial to winning the war. It allows you to buy time and wait for the right opportunity to strike. That's why Churchill was so keen to protect the Suez Canal as well. As leaders, we have to protect and secure our funding, without which we won't have enough time to continue our cause. Economic strength ultimately determines political power; the UK's financial situation at the conclusion of the War determined its decline in the colonial world and America's ascent in the Cold War. 

Know where you have to be to drive the action. Churchill would fly across the Atlantic and Mediterranean very often to speak, cajole, and negotiate with world leaders and generals to coordinate his strategy. If frequent flyer programs existed back then, he must have been the supreme gold member. This shows the importance of showing up at the right place at the right time with the right people. 

Never sacrifice family for your career. It's not worth it. Your love and care for your family is in itself a legacy that gets passed down. Regular escapades are necessary to spend time with family and recuperate from burn outs. Throughout his life, Churchill was so consumed with his war and political life that his children all had severe problems later in life. 

Divine Providence is the determining yet often ignored factor in the course of history. Some people call it luck, but as a Christian, I believe God has His purpose in everything. Many a time Churchill got real close to getting killed by friendly and enemy fire and right before the Normandy invasion, only one panzer division was under Rommel's direct command near the Normandy coast. If it was not so, history would have turned out very differently.