This reading group guide for When Women Lead includes an introduction and discussion questions with author Julia Boorstin. The suggested questions are provoke interesting and lively discussions in your reading group. We hope that these ideas will inspire connection with the women profiled in these pages, self-reflection, and goal setting.

Dear Readers,

In When Women Lead I lay out a new, inclusive vision for leadership. My goal in writing this book was to showcase a diverse set of new leadership icons to inspire people of any gender. I intended for the varied leadership styles and approaches to problem solving of the women in these pages to prompt readers to examine their own traits and how they can be reframed and leveraged as superpowers. We are at a moment when women’s leadership—their empathetic, communal, and purpose-driven approach—is more important than ever.

I hope you will use this book as a guide to defying odds yourself—just like all the women in these pages have. As I’ve traveled the country on my book tour I’ve heard about how both women and men have suffered from insufficient role models to set new patterns in which they could follow. The stories of the women in my book can serve as a beacon, and the data outlining the underlying value of their approach can serve as a blueprint. I’ve seen in my experience and heard from hundreds of women how a lack of understanding about the nature of deep-seated societal biases has prevented success. I hope you will find all the data empowering, and can use the explanation of phenomena, from confirmatory bias to pattern matching, to navigate your own challenges.

Throughout all the gender gaps and bias revealed in my reporting and research, I remain more optimistic than ever. I have seen hundreds of times how women have been able to tap into their own authentic leadership styles to thrive and achieve success on their own terms. A key way women find and pursue their own path is through community. Please strip away any socially imposed concerns that it would be inappropriate to talk about money, lay out audacious goals, or discuss your weaknesses. Don’t try to fit any stereotype of leadership, but rather figure out what you really want, what drives you, and how your differences can be your superpowers. I know we all have them.

Please use a conversation about my book, and the thoughts and feelings it prompts about your own experiences and dreams as a way to connect with a group, class, or community. Use these conversations to identify people who would be a valuable addition to your personal board of advisors. Remember the power in vulnerability—it invites collaboration. And know that no one is born a leader but everyone can become one. I hope the questions posed on the following pages inspire self-reflection, goal setting, and inspiration.

Julia Boorstin​

1. When Women Lead tells a series of stories spotlighting women who have managed to defy the odds to found and run successful companies. Which women’s stories resonated most with you? Are there women who remind you of yourself or a peer? Which of their traits are familiar? Which characteristics or skills that contributed to success were most surprising and counterintuitive to you?

2. The book explains the strategies and skills used to achieve success with a range of research studies and social science experiments. Were there any concepts—like token theory or social sensitivity or beautiful mess effect—that were exciting or validating? Which studies changed your perception of your experience in the workplace? Discuss the study about jockeys that identified how people who are rare in certain roles are underestimated. Did the idea that people are harder on themselves than they are on others resonate? Share your reaction to the sorority and fraternity members solving a murder mystery; does it make sense that the addition of an outsider made the original members of the group smarter?

3. When Women Lead opens with the author recalling how, when she was a teenager, her mother was optimistic that women would be equally represented in leadership positions, and how disappointed she was to see the reality of inequality. How did your family and upbringing frame your expectations of your own opportunity? What do you wish you’d known when you were starting your career that you know now?

4. Have you ever felt underestimated in your professional or personal life? Perhaps both? Share your experiences in the group and discuss the commonalities or differences.

a. Bonus question: Have you ever been able to leverage being underestimated to your advantage? Have you ever been able to surprise people with your skills?

b. Bonus question: Feeling like an outsider can be hard, but have you ever been able to tap into the value of that outsider perspective?

5. Think about the concepts introduced in When Women Lead that explain bias—pattern matching, token theory, the glass cliff, minimum and confirmatory standards, etc. Have you experienced any of those concepts in your work or life? How did you navigate around them? Does learning about these concepts give you ideas about how to better manage them in the future?

6. What are some ways you’ve experienced bias because of your gender or identity? Have you ever directly confronted or rejected stereotypes placed on you? What was the result? Did you face backlash? Did you earn more respect? Bonus question: Talk about a time when you caught yourself applying pattern matching or stereotypes to others or yourself.

7. One theme in this book is how having a purpose beyond just a financial profit helps people and companies succeed and that women face less bias when embracing social or environmental goals. Purpose-driven companies have an advantage in hiring and retaining talent and founders and leaders can draw on their greater purpose to push through challenging times. What do you feel is your purpose beyond succeeding at work? How can you tap into what you’re most passionate about—mentoring people, helping the environment, etc.—to drive your success with work?

8. Make a list of what you consider to be your strengths and your weaknesses. Now, dig into your weaknesses/areas of improvement category. Are you being too critical of yourself? Are there ways to reframe those traits you see as weaknesses? Is there any way to think of them as superpowers?

a. Bonus question: Do you think that the way you saw your shortcomings would be different if you were a different gender or had a different identity? How would you recategorize your traits if your identity matched that of people who have traditionally held positions of authority?

9. Have you ever felt like your ability to achieve a particular goal was limited because of a part of your identity? Have you felt like something core to who you are, like your gender or race, prevented you from succeeding?

a. If you struggled with a limitation, but were still able to succeed, what enabled you to overcome those obstacles? Make a list of the steps you took to navigate those challenges and identify which of those strategies you can deploy again.

b. If you have not been able to overcome challenges tied to your identity, list what you think is preventing your progress. Are there any structural disadvantages laid out in this book, like pattern matching, or the confirmatory standard, that are hindering your progress? Are people judging you more harshly because people with an identity like yours are rare in a particular role? Looking at your list of obstacles, refer back to When Women Lead. Are any of your challenges similar to those faced by the women in the book? How might you be able to emulate their strategies?

10. One of the core messages of When Women Lead is that diversity can drive success. How can you think about the value in bringing in different perspectives to your work? Thinking about intersectionality: Can you broaden your definition of diversity beyond simply gender and race? Can you reframe your company’s approach to investing in diversity from something that’s a nice thing to do to something that provides a financial advantage?

11. Between the studies and the stories, which were some of the most useful lessons that you took from When Women Lead? How can you apply these new tools to navigate adversity or pursue success in your work and life?

12. When Women Leads notes that women are less likely than men to network and pursue audacious professional goals. Do you have a dream job, a fantasy of starting a company, or just a bold personal goal? Write down your ideal position or outcome for yourself in ten years. Then think about how to make this dream a reality. Break down the steps it would take to achieve your most audacious goal over time. Set yourself long-term goals for the next year or two, along with some near-term targets. What would you like to achieve this month? What’s the target you want to stretch and reach for this year?

a. Make a list of all the people you can call upon—friends, colleagues, work contacts—to talk about your goals. Share your dream with them, ask them for advice, and to hold you accountable. Create your own personal board of advisors to help and push you on your journey. You can do it!