Gather initial thoughts and broad opinions about the book.

1. How did your perception of Catherine the Great change from the beginning of the biography to the end? What aspect of her life or character surprised you the most?

2. Massie is renowned for his narrative biographies of Russian rulers. How does Catherine’s story compare to other famous Romanov narratives you might be familiar with, such as those in Massie’s other works like Peter the Great (1980) or Nicholas and Alexandra (1967)?

3. Did you find this book to be more of a political history of an empire or an intimate “portrait of a woman”? Where did you feel the line between Catherine the empress and Catherine the woman was most blurred or most distinct?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Catherine’s success depended on her ability to reinvent herself from a German princess into a thoroughly Russian ruler. When have you had to adapt to circumstances and what did you do?

2. Empress Elizabeth served as Catherine’s volatile and unpredictable mentor, teaching her crucial lessons about power through both kindness and cruelty. What have your own experiences with mentorship been like, and what makes a mentor-mentee relationship effective in your experience?

3. In her early years, Catherine used reading as a refuge and a tool for self-education. How has reading or self-directed learning played a role in your own life? What has it helped you to learn, both in empirical knowledge and in a wider sense?

4. Catherine made a calculated gamble by writing to Empress Elizabeth and asking to be “sent home,” turning a moment of extreme vulnerability into a source of power. Think of a time when someone you know used perceived weakness as a surprising source of strength. How did this work and what changed as a result?

5. Massie presents Catherine as seeking to escape a form of loneliness attached to absolute power. When have you experienced loneliness and how did you seek to lessen it? Were you successful, and why?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The 18th-century concept of an “enlightened despot” suggests that an absolute ruler could use their power to manage progressive reform. How does this idea challenge or reflect our modern beliefs about democracy and effective leadership?

2. The Pugachev rebellion revealed the immense and violent gap between the Russian nobility and the enserfed peasantry. Where do you see similar deep societal fractures today, and what can Catherine’s response teach us about how power structures react to widespread social unrest?

3. The French Revolution served as a crucial ideological test for Catherine, transforming her from an admirer of liberal philosophy into a staunch reactionary. How do societies and their leaders today respond when their foundational ideals are challenged by radical new movements or events? Use examples in your answer.

Dive into the book’s structure, characters, themes, and symbolism.

1. Massie weaves Catherine’s own memoirs and letters throughout the narrative. What effect did hearing Catherine’s voice directly have on your reading experience and your interpretation of her character?

2. What do the recurrent descriptions of military uniforms and drills bring to the biography, and why do you think Massie included them?

3. Analyze the ways that the parallel teenage illnesses of Catherine and Peter function as narrative turning points for the presentation of their subsequent lives.

4. What does Massie argue the evolution of Catherine’s relationship with Gregory Potemkin reveals about her capacity for love and the ultimate demands of autocratic rule? Do you agree? Why or why not?

5. The biography details Catherine’s complicated relationship with her son and heir, Paul. How does their story compare to other famous parent-child succession struggles in 18th-century history or literature?

6. The book’s subtitle is Portrait of a Woman. In what way does Massie use visual description and imagery to engage the reader in his narrative?

Encourage imaginative and creative connections to the book.

1. The Bronze Horseman statue was a masterful piece of political branding that linked Catherine’s legacy to Peter the Great’s. What kind of modern monument or public art project would you design to capture the legacy of her 34-year reign?

2. Imagine that you can make contact with Catherine across time. What would you be most excited to tell her about modern life, society and politics today, especially given her own beliefs and ideals?

3. You’ve been secretly appointed as an advisor to the 14-year-old Sophia upon her arrival in Russia. Based on what you know of her future, what are the three most important pieces of advice you would give her for surviving the court of Empress Elizabeth and securing her position?