I may have to go back and update some of my previous posts on best leadership movies, because The Darkest Hour just bumped the others off the the top spot. It doesn’t require special ability to note leadership lessons in Churchill’s life, so not much is original here, but perhaps the questions in this blog post can be a tool to be intentional about drawing out some of those lessons. In the spirit of Invictus, my most popular post, I offer The Darkest Hour study guide. It’s designed for personal or group reflection after watching the movie.

We learn the most about Churchill from his wife, Clementine. Their interactions as a couple reveal the truth about Churchill as a man much more three-dimensional than the legend most have come to know. Consider these questions about the Churchills and then reflect on how they apply to you.

• Consider the various scenes in which Clementine appears. How does she view him—realistically or with rose-colored glasses? What specific traits does she appreciate about him?
• What does she appeal to in Winston to get him to do what others can’t?

The takeaway quote is this one: “These inner battles have actually trained you for this very moment. You are strong because you are imperfect, you are wise because you have doubts.”

• How do your doubts, weaknesses and imperfections give your leadership strength?

Later the king asks, “Are you not afraid?” Churchill admits, “Most terribly.”

• Do followers expect their leaders to be fearless, or is that an unattainable standard leaders expect of themselves?
• In what ways does the “fearless leader” myth hold back potential leaders?
• How much should a leader let on about his/her own doubts? What are the risks and benefits?

From biographies, we know that one of the first things Churchill does as Prime Minister is to get a realistic assessment of the state of the war. In the film, his War Room depicts the dire state of the British forces. And yet he portrays to the public something very different.

• What steps does Churchill take to get brutally honest information for himself?
• What is the challenge in communicating to the public the state of the war? Do you agree or disagree with his choice to lie to the public? Why?
• What is the line between optimism and inspiration versus honesty? What might have happened had he done it differently?
• Clementine makes an interesting point about truth: “The truth will have its time.” In the film, when is the time for truth? Are the people ready by then?

The early days of Churchill’s time in office are extremely fragile, requiring great courage.

• What is his relationship with the king? How does that relationship change over time, and what factors account for the change?
• Why does he surround himself with a War Cabinet of rivals? What power do Chamberlain and Halifax utilize against him?
• How does Churchill find the leverage to break the opposition and gain the political ground to lead effectively?
• What would courageous leadership look like in your context—with superiors, with rivals and colleagues, and with direct reports?

Churchill struggles with whether his leadership position requires him to consider all possibilities, including entering into negotiations.

• When does focus and principled leadership become myopic and stubborn to the point of blindness? Is it an abdication of leadership to cave on the one point that got you into your position? Why do you think Churchill concludes, “Those who never change their mind never change anything”?
• What is the difference between leading others with a clear vision and looking at the people around you, asking their opinions and seeking out the voice of the people? Is that simply following, or is that also a form of leadership?
• Which factor/whose support most influences his decision to never surrender? The king’s or the people?
• In what ways does Churchill manipulate the various voices to influence the War Cabinet?

There are a lot of other directions you could take in a film discussion, from exploring the shifting nature of Churchill’s reliance on his secretary… to assessing the tradeoffs that come with leadership… to evaluating Chamberlain’s leadership from the back row. If you come up with any other questions or topics of discussion, post them here so we can all benefit.