Dare to Lead

Key Concepts

The Heart of Daring Leadership

“1. You can’t get to courage without rumbling with vulnerability. Embrace the suck.” (p. 10)

“A rumble is a discussion, conversation, or meeting defined by a commitment to lean into vulnerability, to stay curious and generous, to stick with the messy middle of problem identification and solving, to take a break and circle back when necessary, to be fearless in owning our parts, and, as psychologist Harriet Lerner teaches, to listen with the same passion with which we want to be heard.” (p. 10)

“2. Self-awareness and self-love matter. Who we are is how we lead.” (p. 12)

“3. Courage is contagious. To scale daring leadership and build courage in teams and organizations, we have to cultivate a culture in which brave work, tough conversations, and whole hearts are the expectation, and armor is not necessary or rewarded.” (p. 12)

The Four Six Myths of Vulnerability

Myth #1: Vulnerability is weakness. (p. 23)

Myth #2: I don’t do vulnerability. 

Myth #3: I can go it alone. 

Myth #4: You can engineer the uncertainty and discomfort out of vulnerability

Myth #5: Trust comes before vulnerability.

Myth #6: Vulnerability is disclosure. 

“Vulnerability minus boundaries is not vulnerability. It’s confession, manipulation, desperation, or shock and awe, but it’s not vulnerability.” (p. 39)

“Show me a culture in which vulnerability is framed as weakness and I’ll show you a culture struggling to come up with fresh ideas and new perspectives.” (p. 43)

The Vulnerability Armory

1. Armored Leadership: Driving Perfectionism and Fostering Fear of Failure

Daring Leadership: Modeling and Encouraging Healthy Striving, Empathy, and Self-Compassion

2. Armored Leadership: Working from Scarcity and Squandering Opportunities for Joy and Recognition

Daring Leadership: Practicing Gratitude and Celebrating Milestones and Victories

3. Armored Leadership: Numbing 

Daring Leadership: Setting Boundaries and Finding Real Comfort

4. Armored Leadership: Propagating the False Dichotomy of Victim or Viking, Crush or Be Crushed

Daring Leadership: Practicing Integration—Strong Back, Soft Front, Wild Heart

“For me, that strong back is grounded confidence and boundaries. The soft front is staying vulnerable and curious. The mark of a wild heart is living out these paradoxes in our lives and not giving into the either/or BS that reduces us. It’s showing up in our vulnerability and our courage, and, above all else, being both fierce and kind.” (p. 90)

5. Armored Leadership: Being a Knower and Being Right

Daring Leadership: Being a Learner and Getting It Right 

“There are three strategies that I’ve seen work to transform always knowing into always learning. First, name the issue. It’s a tough conversation, but clear is kind: I’d like for you to work on your curiosity and critical thinking skills. You’re often quick with answers, which can be helpful, but not as helpful as having the right questions, which is how you’ll grow as a leader. We can work together on this. Knowers often have a lot of people talking behind their backs, and that’s unkind. Second, make learning curiosity skills a priority. Third, acknowledge and reward great questions and instances of ‘I don’t know, but I’d like to find out’ as daring leadership behaviors. The big shift here is from wanting to “be right” to wanting to ‘get it right.’” (p. 92)

6. Armored Leadership: Hiding Behind Cynicism 

Daring Leadership: Modeling Clarity, Kindness, and Hope

7. Armored Leadership: Using Criticism as Self-Protection

Daring Leadership: Making Contributions and Taking Risks 

8. Armored Leadership: Using Power Over 

Daring Leadership: Using Power With, Power To, and Power Within

“Power with ‘has to do with finding common ground among different interests in order to build collective strength. Based on mutual support, solidarity, collaboration, and recognition and respect for differences, power with multiplies individual talents, knowledge, and resources to make a larger impact.’” (p. 97)

“Power to translates to giving everyone on your team agency and acknowledging their unique potential. It is ‘based on the belief that each individual has the power to make a difference, which can be multiplied by new skills, knowledge, awareness, and confidence.’” (p. 97)

“Power within is defined by an ability to recognize differences and respect others, grounded in a strong foundation of self-worth and self-knowledge. When we operate from a place of power within, we feel comfortable challenging assumptions and long-held beliefs, pushing against the status quo, and asking if there aren’t other ways to achieve the highest common good.” (p. 97)

9. Armored Leadership: Hustling for Your Worth

Daring Leadership: Knowing Your Value 

“Getting clear on our value and our team members’ values will revolutionize our company and create lanes where none might have existed before—instead of a ten-person race, we start to develop a coordinated relay in which team members baton-toss to each other’s strengths instead of vying to run the whole stretch alone. Once everyone understands their value, we stop hustling for worthiness and lean into our gifts.” (p. 98)

10. Armored Leadership: Leading for Compliance and Control (p. 98)

“The armor of compliance and control is normally about fear and power. When we come from this place, we often engage in two armored behaviors: 

• “We reduce work to tasks and to-dos, then spend our time ensuring that people are doing exactly what we want, how we want it—and then constantly calling them out when they’re doing it wrong.” (p. 99)

• “When we operate from compliance and control, we also have a tendency to hold on to power and authority, and push only responsibility down. This leads to huge alignment issues for people.” (p. 99)

Daring Leadership: Cultivating Commitment and Shared Purpose 

11. Armored Leadership: Weaponizing Fear and Uncertainty

Daring Leadership: Acknowledging, Naming, and Normalizing Collective Fear and Uncertainty 

12. Armored Leadership: Rewarding Exhaustion as a Status Symbol and Attaching Productivity to Self-Worth 

Daring Leadership: Modeling and Supporting Rest, Play, and Recovery 

13. Armored Leadership: Tolerating Discrimination, Echo Chambers, and a “Fitting-in” Culture 

Daring Leadership: Cultivating a Culture of Belonging, Inclusivity, and Diverse Perspectives

14. Armored Leadership: Collecting Gold Stars 

Daring Leadership: Giving Gold Stars 

15. Armored Leadership: Zigzagging and Avoiding

Daring Leadership: Talking Straight and Taking Action 

“When we find ourselves zigzagging—hiding out, pretending, avoiding, procrastinating, rationalizing, blaming, lying—we need to remind ourselves that running is a huge energy suck and probably way outside our values. At some point, we have to turn toward vulnerability and make that call.” (p. 110)

16. Armored Leadership: Leading from Hurt

Daring Leadership: Leading from Heart 

Shame holds back organizations

“What’s trickier is that in most cases, shame is hidden behind the walls of organizations. It’s not dormant—it’s slowly eating away at innovation, trust, connection, and culture—but it’s tougher to spot. Here’s what to look for: 

“Perfectionism 

“Favoritism 

“Gossiping 

“Back-channeling 

“Comparison 

“Self-worth tied to productivity 

“Harassment 

“Discrimination 

“Power over 

“Bullying 

“Blaming 

“Teasing 

“Cover-ups” (p. 131)

Empathy skills

Empathy Skill #1: To see the world as others see it, or perspective taking (p. 143)

Empathy Skill #2: To be nonjudgmental (p. 145)

Empathy Skill #3: To understand another person’s feelings (p. 146)

Empathy Skill #4: To communicate your understanding of that person’s feelings (p. 146)

Empathy Skill #5: Mindfulness (p. 148)

“The word mindfulness can get on my nerves sometimes, so I opt for paying attention.” (p. 149)

“Grounded Confidence = Rumble Skills + Curiosity + Practice”

“Here are some specific rumble starters and questions that we use: (p. 172)

1. “The story I make up…” (p. 172)

2. “I’m curious about…

3. “Tell me more. 

4. “That’s not my experience (instead of “You’re wrong about her, him, them, it, this…”).

5. “I’m wondering… 

6. “Help me understand… 

7. “Walk me through… 

8. “We’re both dug in. Tell me about your passion around this. 

9. “Tell me why this doesn’t fit/work for you. 

10. “I’m working from these assumptions—what about you? 

11. “What problem are we trying to solve?” (p. 173)

The BRAVING Inventory

“Boundaries: You respect my boundaries, and when you’re not clear about what’s okay and not okay, you ask. You’re willing to say no.” (p. 225)

“Reliability: You do what you say you’ll do. At work, this means staying aware of your competencies and limitations so you don’t overpromise and are able to deliver on commitments and balance competing priorities.” (p. 225)

“Accountability: You own your mistakes, apologize, and make amends.” (p. 225)

“Vault: You don’t share information or experiences that are not yours to share. I need to know that my confidences are kept, and that you’re not sharing with me any information about other people that should be confidential.” (p. 225)

“Integrity: You choose courage over comfort. You choose what is right over what is fun, fast, or easy. And you choose to practice your values rather than simply professing them.” (p. 225)

“Nonjudgment: I can ask for what I need, and you can ask for what you need. We can talk about how we feel without judgment. We can ask each other for help without judgment.” (p. 226)

“Generosity: You extend the most generous interpretation possible to the intentions, words, and actions of others.” (p. 226)

The Revolution

“If you asked me to boil down everything I’ve learned from this research, I would tell you these three things:

1. “The level of collective courage in an organization is the absolute best predictor of that organization’s ability to be successful in terms of its culture, to develop leaders, and to meet its mission. 

2. “The greatest challenge in developing brave leaders is helping them acknowledge and answer their personal call to courage. Courage can be learned if we’re willing to put down our armor and pick up the shared language, tools, and skills we need for rumbling with vulnerability, living into our values, braving trust, and learning to rise.

3. “We fail the minute we let someone else define success for us. Like many of you, I spent too many years taking on projects and even positions, just to prove I could do it. I was driven by a definition of success that didn’t reflect who I am, what I want, or what brings me joy. It was simply accomplish-acquire-collapse-repeat. There was very little joy, very little meaning, and tons of exhaustion and resentment.” (p. 271)

Quotables

“Our ability to be daring leaders will never be greater than our capacity for vulnerability.” (p. 11)

“Daring leaders must care for and be connected to the people they lead.” (p. 12)

Rumble Tool: The Square Squad. “Here’s the solution we shared in Daring Greatly: Get a one-inch by one-inch piece of paper and write down the names of the people whose opinions of you matter. It needs to be small because it forces you to edit. Fold it and put it in your wallet. Then take ten minutes to reach out to those people—your square squad—and share a little gratitude. You can keep it simple: I’m getting clear on whose opinions matter to me. Thank you for being one of those people. I’m grateful that you care enough to be honest and real with me.” (p. 22)

“If you read these stories and think Who has the time? I’d ask you to calculate the cost of distrust and disconnection in terms of productivity, performance, and engagement. Here’s what I know to be true from my experience and what I consider to be one of the most important learnings from this research: Leaders must either invest a reasonable amount of time attending to fears and feelings, or squander an unreasonable amount of time trying to manage ineffective and unproductive behavior.” (p. 67)

“Today we pay a lot of lip service to the idea of ‘bringing your whole self to work’—yet the organizations that actually allow employees to do that are few and far between. I don’t see a tremendous amount of meaningful, actionable support for integration and wholeheartedness in most companies. The slogan is easy. The behaviors to support the slogan are not.” (p. 73)

“The hopeful news is that there are some tasks that humans will always be able to do better than machines if we are willing to take off our armor and leverage our greatest and most unique asset—the human heart. Those of us who are willing to rumble with vulnerability, live into our values, build trust, and learn to reset will not be threatened by the rise of the machines, because we will be part of the rise of daring leaders.” (p. 75)

“Something as simple as starting or ending meetings with a gratitude check, when everyone shares one thing they’re grateful for, can build trust and connection, serve as container-building, and give your group permission to lean into joy.” (p. 83)

“There is incredible relief and power in naming and normalizing fear and uncertainty. We have to find the courage to look back at the people who are looking at us for leadership and say, ‘This is difficult. There are no simple answers. There is pain and fear that would be easy to unload on others—but that would be unfair and out of our integrity. We will walk through this in a way that makes us feel proud. It will be hard, but we will do it together.’” (p. 105)

“The majority of shame researchers and clinicians agree that the difference between shame and guilt is best understood as the difference between ‘I am bad’ and ‘I did something bad.’” (p. 128)

“In my own life, this translates to one simple mandate: Talk to yourself the way you’d talk to someone you love.” (p. 158)

“Remember, empathy is the most powerful connecting and trust-building tool that we have, and it’s the antidote to shame. If you put shame in a petri dish and cover it with judgment, silence, and secrecy, you’ve created the perfect environment for shame to grow until it makes its way into every corner and crevice of your life. If, on the other hand, you put shame in a petri dish and douse it with empathy, shame loses its power and begins to wither.” (p. 160)

“Another helpful curiosity tool is staying on the lookout for horizon conflict. Our role dictates where we should set our lens in terms of the organizational horizon. As a founder and CEO, I’m expected to plot a long-term course for the company. I try to bounce back and forth from a ten-year horizon to the current state of affairs. Other leaders on my team have responsibility for different horizons. An operations leader may be focused on a six-month horizon because of a huge launch schedule.” (p. 174)

“The most important seats in the arena, the ones we need to be able to focus on, especially in difficult times, are reserved for empathy and self-compassion. In the empathy seat, or seats, we just need one or two people who know our values and support our efforts to put them into action. And the self-compassion seat is for us. It’s a reminder that if we can’t cheer ourselves on, we shouldn’t expect others to do it. If we don’t make our values priorities, we can’t ask others to do it for us.” (p. 195)