Dare to Lead

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

1. Brown argues that vulnerability is not weakness but rather our greatest measure of courage. When have you experienced the power of vulnerability in your professional life, and what happened when you decided to take that risk?

2. The book introduces the concept of “permission slips” to encourage thoughtful communication in meetings. What permission would you write for yourself to address a current professional or personal challenge?

3. Brown depicts shame as the painful feeling that we are flawed and that our flaws define who we are. How have you observed shame-based behaviors in your own workplace culture? What strategies from the book might help address them?

4. The author suggests that real confidence emerges when we acknowledge vulnerability and learn from failures. Was there a time when failure led to greater confidence or growth in your life? How did your experience align with Brown’s concept of “grounded confidence”?

5. Brown writes about living into our values by identifying specific behaviors that reflect those values. Which two values would you identify as your core values, and what specific behaviors demonstrate these values in your daily life?

6. The book discusses how people often resort to “armoring up” when facing difficult situations. Which of Brown’s described armor tactics (perfectionism, cynicism, numbing, etc.) do you recognize in yourself, and how might you practice more vulnerability instead?

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

1. Brown suggests that our culture often confuses leadership with control and achievement with domination. How do you see these misconceptions playing out in contemporary workplace cultures or leadership models?

2. The book challenges traditional notions of professional behavior by advocating for emotional awareness in leadership. How do societal expectations about workplace professionalism help or hinder the implementation of Brown’s leadership approach?

3. Brown discusses how perfectionism and workaholism are often celebrated in professional settings despite their negative impacts. How do these values reflect broader societal attitudes toward work, success, and personal worth in contemporary culture?

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

1. Brown deliberately uses colloquial terms like “rumbling with vulnerability” instead of more clinical language (10). How does her choice of accessible, metaphorical vocabulary affect your engagement with the leadership concepts she presents?

2. Throughout the book, Brown employs various metaphors, such as “emotional armor” and “the arena.” Which metaphor did you find most illuminating, and how did it enhance your understanding of her leadership philosophy?

3. Brown structures her book around four skill sets: “Rumbling with Vulnerability,” “Living into Our Values,” “Braving Trust,” and “Learning to Rise” (10). How effective is this organizational approach in developing her argument about daring leadership?

4. The author uses personal anecdotes to illustrate her points about vulnerability and leadership. Select one story that particularly resonated with you and analyze how it supports her larger arguments.

5. The book integrates research findings with practical advice. How does Brown balance theory with practical application? What effect does this balance have on the book’s persuasiveness and value as a tool for leaders?