1-Page Summary

Should leaders allow themselves—or their employees—to be vulnerable? Many organizations say no. But in Dare to Lead, researcher Brené Brown argues that courageous leaders who allow vulnerability—in themselves and in others—are essential to thriving work cultures. In this guide, you’ll learn the four skills you must practice in order to lead courageously—facing vulnerability, choosing and practicing values, building trust, and developing failure resilience—and how using these skills effectively can help your team overcome difficult situations and encourage creativity and innovation. Along the way, you’ll learn suggestions from other experts on the best ways to practice these skills.

Skill #1: Face Vulnerability

According to Brown, the first skill you must practice in order to become a courageous leader is to face vulnerability. She explains this is a vital skill because you can only build an innovative, creative work culture if your team feels comfortable failing and taking risks.

In this section, we’ll first define vulnerability: What exactly is it, and why is it essential that we understand it well? Then, we’ll name the benefits of facing vulnerability.

What Is Vulnerability?

Brown defines vulnerability as exposure to the risk of failure or emotional harm. However, she argues, most people have three main misconceptions about vulnerability—which leads them to avoid it.

Misconception #1: Being vulnerable means you’re weak. As Brown notes, people often view their refusal to acknowledge vulnerable feelings as a courageous act. However, she argues that it signals the opposite: They’re not brave enough to engage with their vulnerability. Rather, Brown contends, feeling vulnerable is a sign that you were courageous enough to approach—not avoid—exposure to risk and uncertainty.

The Difference Between Vulnerability and Weakness

In her earlier book, The Power of Vulnerability, Brown explains that many people who are in a position where showing weakness can be harmful—like executives—mistakenly associate weakness with vulnerability and so believe they can’t be vulnerable. But in Daring Greatly, Brown elaborates further on the difference between vulnerability and weakness, explaining that Merriam-Webster defines vulnerability as “open to attack or damage,” while weakness is “the inability to withstand attack or wounding.” In other words, being vulnerable means that you’re open to harm but not totally defenseless. Moreover, she presents studies that prove that acknowledging your vulnerability makes you stronger: If you don’t acknowledge your vulnerability, you’re not prepared to protect yourself.

Misconception #2: You have to trust someone in order to be vulnerable with them. Brown contends that this misconception explains why people refuse to be vulnerable with people they don’t know well. However, Brown argues that vulnerability and trust happen simultaneously, in a constant exchange of small moments; neither comes before the other. As Brown explains, when someone reaches out to you and you choose to engage with and respond to their vulnerability (instead of ignoring it), you earn their trust and the right to be vulnerable with them in turn.

(Shortform note: While Brown argues that vulnerability and trust happen simultaneously, Start With Why author Simon Sinek argues that trust comes before vulnerability: In the workplace, employees must trust their leaders before they feel vulnerable enough to take risks. So how, as a leader, can you get your employees to trust you? Sinek explains that trust is based on shared beliefs: We believe that someone who shares our beliefs is more likely to have our backs and not take advantage of us. So you can earn your employees’ trust by showing them that you share their values.)

Misconception #3: Being vulnerable means you have to share everything. Brown clarifies that courageous leaders practice vulnerability with limits and don’t overshare personal feelings or information with their team. Instead, they talk openly about the emotions surrounding uncertain but work-relevant situations—like a new product launch.

(Shortform note: As a leader, how can you effectively create a boundary on what you will—or won’t—share with your team? Try creating SMART boundaries: Your boundaries should be Specific, Mutable—in other words, flexible based on the situation, About You—not about what others do near you, Reasonable, and Talked Through—in other words, you communicate them and compromise on them if necessary.)

The Benefits of Facing Vulnerability

Now that you understand what vulnerability is, we’ll discuss the benefits of productively engaging with it—and teaching your team members the value of doing so. Brown names three benefits of facing vulnerability: It helps you have tough conversations, discourages defensive behaviors, and helps you understand and overcome shame.

Benefit #1: Facing Vulnerability Helps You Have Tough Conversations

As Brown notes, leaders must sometimes have tough conversations that have uncertain outcomes or demand emotional exposure from either party. However, she argues that being vulnerable enough to clearly say what you mean will help you make honest, productive connections.

(Shortform note: Clearly saying what you mean may not help you make positive connections in all cultures. In The Culture Map, cultural expert Erin Meyer explains that, while the United States prizes direct negative feedback, many other cultures traditionally provide negative feedback indirectly—like by couching their message with positive affirmations—and so may perceive direct negative feedback as harsh and cruel. To avoid this, Meyer recommends that Americans working in other cultures be transparent about how they normally provide feedback so that their employees can adjust their expectations accordingly.)

Being vulnerable also prevents two issues that can arise from unclear language. First, Brown explains that using unclear language may put your team in situations where they’re unfairly held accountable for expectations they don’t clearly understand. Brown explains that if you’re uncomfortable with vulnerability, you may struggle to be honest and instead say a polite half-truth to avoid discomfort. However, this lack of honesty hurts your team members, especially if you’re providing feedback: The recipient receives no indication that they need to improve, yet they’re held accountable for their lack of improvement. But when you use clear language, your team knows exactly what is expected of them.

(Shortform note: In Principles, hedge fund founder Ray Dalio recommends practicing “extreme honesty” to help your organization make better decisions. This means that everybody in your organization commits to revealing their thoughts instead of putting a filter on or hiding them. In such an environment, you don’t have to worry about hurting other people. This allows you to give truthful feedback on someone’s foolish decision before they follow through on it so that you can prevent its negative consequences.)

Second, Brown explains that if your team uses unclear language, it may hinder your ability to help them. As Brown notes, people who struggle to be vulnerable may avoid talking about their true emotions; instead, they’ll name “easy” but inaccurate emotions so they can talk about their feelings without full emotional exposure. But if you don’t know exactly what your team member is feeling, you won’t appropriately connect to or solve the root of their problem; in contrast, understanding their feelings allows you to provide the best possible solution.

For example, you might respond to your team member saying “I’m stressed” by giving them a few days off. But if it turns out that your team member is actually scared of being fired, your solution may amplify their fears because they worry that you don’t need them at the company. But if you had made them comfortable enough to say “I’m scared,” you could have eased their fears by discussing how they’re indispensable to the company.

(Shortform note: Your employees may also struggle to tell you exactly what they’re feeling—in other words, to give you feedback on their work environment—because they’re afraid of offending you or hurting their careers. In No Rules Rules, Erin Meyer and Netflix CEO Reed Hastings recommend making it easier for employees to give you feedback by including “feedback” as an agenda item in one-on-one meetings.)

Benefit #2: Facing Vulnerability Discourages Defensive Behaviors

Another benefit of facing vulnerability, Brown argues, is that it discourages defensive behaviors.

Brown explains that unless you encourage your employees to face their vulnerability, they’ll naturally adopt defensive behaviors, which are behaviors that protect them from experiencing any negative emotions. But these behaviors, Brown argues, usually stifle innovation and creativity.

The defensive behaviors Brown names include the following:

Other Ways People Respond to Negative Emotions

In Awaken the Giant Within, life coach Tony Robbins also suggests that people who face negative emotions may respond by trying to avoid them—which is what both perfectionists and critics do.

However, Robbins adds two more unhealthy behaviors people resort to when they face negative emotions: First, they may go into denial and try to dissociate from the emotion. Second, they may internalize the emotion and turn it into part of their identity. For example, instead of trying to avoid the shame of making a mistake by becoming a perfectionist, they might instead try to develop a reputation as the lovable goof who’s constantly messing up at work—which would stifle innovation by forcing your team to spend time fixing this employee’s mistakes.

To combat these behaviors, Brown recommends creating a work culture where team members are comfortable facing vulnerability and understand that risk and failure are both tolerated and useful. She names three specific steps for doing so.

  1. Stop rewarding defensive behaviors. You could be doing this consciously, like when you commend a team member for never making a mistake, or unconsciously, like if you allow someone to criticize without following up with their own idea.
  2. Open up honest conversations with team members acting defensively. Clearly name the behavior, question the emotional source of it, and suggest how they can improve.
  3. Recognize team members who try to be more vulnerable. Present their efforts —such as asking questions and asking for help or taking responsibility for their mistakes—as an example for other team members to follow.

Why Demonstrating Vulnerability Matters

In How Will You Measure Your Life?, business consultant Clayton Christensen elaborates on why it’s essential for leaders to demonstrate that they value vulnerability instead of merely saying that they do. Christensen explains that a company culture is its employees’ instinctive sense of the company’s priorities and processes, which they learn over time by seeing how the company works toward its priorities. So if a leader defines a culture but doesn’t embody or enforce it, the company will evolve a different culture based on the priorities and processes that the employees actually see.

As such, by refusing to reward defensive behaviors, talking with team members acting defensively instead of yelling at them, and rewarding vulnerability, you prove to your employees that you value vulnerability and are not just paying lip service to it. This teaches them that they can feel more comfortable feeling and acting vulnerably in return—instead of resorting to defensive behaviors.

Benefit #3: Facing Vulnerability Helps You Understand and Overcome Shame

The final benefit of facing vulnerability, Brown argues, is that it helps you understand and overcome shame—the feeling that you’re a flawed person who’s not worthy of connection or belonging. This matters for leaders, according to Brown, because shame drives toxic behaviors—like bullying at work.

(Shortform note: How does shame drive toxic behaviors like bullying? Brown doesn’t specify in this book, but she does present research on it elsewhere: She argues that people bully others in an effort to hide their own feelings of shame.)

Brown explains that to overcome shame, you must talk through it. As a leader, you can support your team members in this process by encouraging them to discuss their struggles with you, and responding to these struggles with empathy. By doing so, you’ll demonstrate to team members how they can practice empathy among themselves. Moreover, your team members will be more likely to take risks in the future if they know they’ll be supported if they struggle.

(Shortform note: Why does expressing empathy help people overcome shame? Although Brown doesn’t explain this in Dare to Lead, she does present research on this elsewhere: Brown explains that practicing empathy—in other words, connecting with someone—proves that they are worthy of connection and thus reduces their shame, or their feeling that they’re not worthy of connection.)

To effectively practice empathy, Brown notes, you must understand that empathy is a connection with the emotions tied to someone’s struggle or failure—not just an attempt to make things better. So when your team struggles, focus on being nonjudgmental, understanding the emotions of the other person, and opening up the opportunity to talk about the feelings surrounding the experience. For example, after a team member has a tough presentation, you can respond with empathy by saying, “I’m really sorry for how that presentation went. I know it can be embarrassing. Do you want to talk about it?”

(Shortform note: Brown’s recommendations for practicing empathy reflects the three types of empathy described by psychologists Daniel Goleman and Paul Ekman. Being nonjudgmental indicates cognitive empathy—your ability to understand others’ perspectives. Understanding others’ emotions is the definition of emotional empathy. And asking about others’ feelings indicates compassionate empathy—the actions you take based on the empathy that you feel towards others. Even though compassionate empathy usually is an attempt to make things better, it still counts as empathy because you’re acting based on your understanding of others’ emotions and not disregarding them totally.)

Skill #2: Choose and Practice Your Values

You now know why it’s important to face vulnerability—but how do you actually develop the courage to do so? Brown contends that this develops partly from the second skill of courageous leadership: choosing and practicing your values. In this section, we’ll first discuss the importance of leading with grounded confidence and why practicing your values is essential to that. Then, we’ll discuss how to choose and practice these values in your organization—especially when giving feedback.

Leading With Grounded Confidence: Practicing Values, Curiosity, and Self-Awareness

Brown contends that, when faced with vulnerable moments or tough decisions, brave leaders depend on “grounded confidence” for the courage to face their vulnerability instead of hiding behind defensive behaviors. Brown defines “grounded confidence” as confidence rooted in strong values, self-awareness, and curiosity; it’s based on a proven ability to face your vulnerability rather than a contention that you probably could.

(Shortform note: Brown’s description of “grounded confidence” is nearly identical to the definition of confidence described in The Confidence Code by Katty Kay and Claire Shipman. They argue that confidence is a strong belief that you can perform a skill because you’ve already proven that you can do it—although they also add that this belief is so strong that it drives you to perform the skill in question.)

Brown argues that grounded confidence has two components. The first is to approach your work with curiosity; in other words, wonder what might happen instead of panicking about an uncertain outcome. With this approach, you’ll take the time to examine problems and possible solutions, instead of racing for an answer and missing valuable learning opportunities.

(Shortform note: In Essentialism, author Greg McKeown suggests that in order to rationally evaluate all your options, you must have the following: a separate space to explore your options, time to think about why your decision matters, imagination to increase the number of creative connections you might make, a good night’s sleep so that you can perform at your optimum level, and clear selective criteria so you know how to decide which option is best.)

The second component of grounded confidence, according to Brown, is continually practicing your values and self-awareness. She argues that if you act in accordance with your values in everyday situations, you will also do so in moments of vulnerability because it’s become second nature. Brown admits that these moments of vulnerability will never be easy, but with well-practiced values—and the self-awareness to recognize and refute the temptation to resort to defensive behaviors—you’ll have the confidence to face these moments, knowing fully that you’ll make it to the other side.

(Shortform note: Practicing the second component of grounded confidence may also improve your self-esteem, according to self-esteem expert Nathaniel Branden. In The Six Pillars of Self-Esteem, he argues that you can improve your self-esteem by recognizing and acting on every reality that affects your life and by regularly acting in accordance with your values—both of which you do each time you recognize that you’re tempted to resort to defensive behaviors and choose to live by your values instead.)

How to Practice Your Values

Now that you know why you should practice your values, we’ll discuss how to practice them.

The first step, according to Brown, is to have your organization choose no more than two core values that employees can depend on to guide tough decisions. If you have too many values, Brown explains, they become meaningless and too nebulous to be actionable. Imagine that you say, “We care about quality, collaboration, sustainability, balance, and knowledge.” These are all worthy values, but there are so many, so it’s hard to know which one should be driving behaviors and major decisions.

The second step, according to Brown, is to translate these values into behaviors that can be taught, practiced, and evaluated. These behaviors will provide clear guidelines of how you expect your team members—and yourself—to work together, make decisions, and show up to their work. For example, say that your company decides on balance and knowledge as their two core values. The balance value might translate into a “no work emails on the weekend” policy, and the knowledge value might translate to an expectation that everyone comes to the weekly marketing meeting with a question or a new tool or skill to share.

Other Ways to Choose and Practice Your Values

Like Brown, Traction author Gino Wickman also argues that having core values will help guide your company through difficult situations. However, he presents different ways of choosing and practicing them.

Notably, Wickman argues that you should have three to seven core values—not just two—and recommends a four-step process for choosing them:

  1. Think of three people in your company who stand out as star performers.
  1. List the characteristics these people embody.
  1. Combine similar values and narrow the list.
  1. Pick out the values that seem most important, reflect on them for a month, then finalize them.

What do you do once you’ve chosen these values? Instead of translating them into behavioral guidelines, as Brown suggests, Wickman recommends communicating your values to your employees by presenting them with stories and examples of people in your company applying that value. Additionally, Wickman suggests hiring people who’ve already exhibited those values because they’ll likely fit in better with your company culture. To do so, Wickman recommends explaining your values to candidates in the interview process and asking them how they’ve applied them in their previous work.

How Strong Values Support the Feedback Process

According to Brown, practicing your values is especially important when giving and receiving feedback—a vulnerable process that often prompts defensive behaviors. When giving feedback, focusing on your values can help you approach the conversation in alignment with them. For example, having the core value of teamwork might push you to work together with your feedback recipient to come up with solutions.

Brown adds that when receiving feedback, focusing on your values can help you channel your emotions productively, toward insight and learning, rather than defensively. You can do this by entering the conversation with a value-supporting mantra or behavior, such as “Paying attention will make me a better teammate” (teamwork), or “I will ask questions and fully understand” (curiosity).

(Shortform note: In Thanks for the Feedback, Douglas Stone and Sheila Heen present an alternative way to ensure that you receive and respond to feedback productively: Understand your triggers, or the knee-jerk responses that cause you to dismiss or get angry about feedback. Understanding these responses, they explain, will help you gain control over them. For example, you may negatively respond to feedback because your colleague—and not your boss—is giving it to you, even though she’s making a valid point. But if you understand that feedback from this specific colleague triggers you, you can separate your frustrations about who is giving you the feedback from your receptivity to the content of the feedback.)

Skill #3: Build Trust and Connection

Brown contends that the third skill of courageous leadership is building trust and connection. In this section, we'll first discuss why trust matters and why people shy away from discussing it. Then, we’ll discuss how you can increase trust within your organization.

Brown explains that trust is essential to organizations: It allows people to feel comfortable trying new ideas and relying on others. However, Brown argues that we often don’t trust our colleagues—but we don’t talk about this to avoid offending our colleagues by calling them untrustworthy.

(Shortform note: Other researchers agree with Brown that trust is essential to organizations. Specifically, they contend that you must have two types of trust: competence trust, or a belief that your colleagues will do good work, and interpersonal trust, or a belief that others are doing their best. But what if a colleague doesn’t extend these types of trust to you? Instead of becoming offended, remember that trust is not an either/or proposition. In Crucial Conversations, the authors argue that trust can evolve and is specific to the situation—so just because someone distrusts you in some circumstance doesn’t mean they distrust you in all circumstances.)

How to Talk About Trust

To make the conversation about trust less emotional, Brown recommends that you reframe the discussion: Talk about trustworthy behaviors instead of the general sense of trust you have in someone. By doing so, you break down the nebulous concept of trust into actionable behaviors that you—and your team—can work on to improve trust. For example, if you say, “I don’t trust you with this project,” your team member may grow angry. But if you say, “I want to discuss some reliability issues when it comes to meeting deadlines,” your team member understands exactly why you have lower trust in them and how they might improve.

What, exactly, are trustworthy behaviors? Brown explains that these are behaviors you perform in everyday situations—not grand gestures. Namely, behaving in a trustworthy manner means that you set and respect limits, stick to your commitments, take responsibility for your mistakes, keep confidences, and generally assume that others are trying their best.

Why Trustworthy Behaviors Work

If you can build trust by practicing specific behaviors, you may assume that trust is something that behaves logically: For example, if a company presents data that proves that they’re doing something right, you automatically trust them. However, in Start With Why, Sinek explains that trust is a gut feeling that can’t be rationalized because it’s located in the limbic brain—our emotional center. This explains why we trust certain companies even when things go wrong but mistrust other companies that do everything right. But in this case, why would practicing trustworthy behaviors help build trust?

As Brown notes, you can earn people’s trust by showing them that you share their values and beliefs. So it’s possible that the trustworthy behaviors Brown recommends build trust because they’re all behaviors that demonstrate your values. Setting and respecting limits implies that you value boundaries, sticking to your commitments and keeping confidences imply that you value integrity, taking responsibility implies that you value accountability, and assuming the best in others implies optimism.

Brown emphasizes that assuming that others are trying their best is particularly important, as it can reveal how your leadership might be causing untrustworthy behaviors. As Brown notes, if someone falls short on a task, it’s easy to assume the worst—like that they don’t care. But if you assume that they were trying their best, it prompts you to examine how you may have failed as a leader: For example, perhaps you gave unclear guidelines. When you change your actions according to what you learn—like by providing clearer guidelines—it rebuilds trust on both ends: You are able to restore your trust in your team member’s abilities, while they learn that they can trust you not to give them tasks that they can’t accomplish.

(Shortform note: What should you do if someone falls short on a task, and it turns out that it is their responsibility—not yours? In Crucial Conversations, the authors recommend that you try to rebuild trust incrementally: Start by trying to trust them in the moment, allowing yourself not to trust them in all circumstances. Say you’ve lost trust in your colleague because he missed an important deadline. You should start trying to rebuild trust by trusting that he’s working when he says he is; it’s OK to not trust him to turn in his next project on time.)

Skill #4: Develop Failure Resilience

Brown contends that the fourth skill of courageous leadership is developing your team’s failure resilience—the ability to recover and move on quickly after something goes wrong. This is an essential skill for leaders to teach because people are more likely to take risks and try new ideas if they’re confident that they can recover from any setback.

Brown recommends that you teach failure resilience from the very beginning of the onboarding process, in order to normalize failure and demonstrate that team members will be supported, not shamed, when (not if) it happens. Otherwise, you’ll waste time fixing the defensive behaviors that arise from the fear of failure, like the perfectionism we discussed previously.

How to Make Employees Feel Safe From the Beginning

In The Culture Code, Daniel Coyle also contends that to make an employee safe enough to fail, you should start early in her journey with the company because the sooner she feels safe with your company, the sooner she can behave productively—instead of engaging in unproductive, defensive behaviors.

Coyle defines the behaviors and actions that create a supportive environment in the office as “belonging cues” and suggests three things to do on an employee’s first day. First, show interest in her excitement; you’ll show her that you value her as an individual and help her feel connected to others. Second, show her how she might be promoted so that she can see what kind of future she has with the organization. Third, express that you value openness, transparency, and feedback to signal that she can speak up without fear of being fired.

According to Brown, failure resilience has two main components: recognizing your emotional response to failure and working through the story you create about failure.

Step 1: Recognize Your Emotional Response

Brown explains that while you don’t need to know exactly what you’re feeling in response to a failure or setback, you need to acknowledge that your emotions were triggered in some way. By following this step, you go from feeling to thinking—instead of leaping directly to problematic defensive behavior.

Step 2: Work Through Your Initial Story

Brown explains that when you encounter failure, you naturally create a story to explain what happened and why. But since this “initial story” is based on incomplete information and your own insecurities, it tends to include connections that may or may not be true.

To work through the story productively, you need to question its different components to separate facts from assumptions and insecurities. Ask yourself: What do I actually know about the situation? What am I assuming about the other people in the situation? What feelings are driving my reaction?

Then, talk through your story aloud with the people involved. The phrase, “The story I'm telling myself…” is especially useful in these conversations—it lets you express your feelings and invite the other person to share their side of the story. Approaching the story this way either shows you the illogical leaps your story made or opens up an honest conversation about her thoughts.

For example, say you present an idea in a meeting and your colleague Anne glances at another colleague before rejecting your idea. Your initial story might be, “Anne looked at Cheryl before saying no. That must mean they’ve been talking about me and think my ideas are stupid and not worth their time.” But by reviewing this story, you realize that you only know that Anne looked at Cheryl and she rejected your idea.

Once you understand these feelings, you speak to Anne, saying, “When I brought up that idea, you looked at Cheryl before you said no. The story I’m telling myself is that you two have been discussing my ideas outside the meeting and don’t think they’re worth your time.” Then, Anne might simply say, “No, I was looking at the clock behind Cheryl because I had a deadline that day that I was behind on,” which would bring you great relief.

How to Talk About Failure: What Other Authors Say

The Crucial Conversations authors would likely characterize any conversation about failure as a “crucial conversation,” which they define as a discussion characterized by high stakes, differing opinions, and strong emotions. Their process for having such a discussion is similar to Brown’s, but they have additional suggestions that may help you work through failure even more productively.

Like Brown, the authors contend that in order to prevent yourself from engaging in problematic defensive behaviors, you must acknowledge that your emotions were triggered and re-examine the initial story that you created. They add that to do so effectively, you must understand that your emotions are not created by others; rather you create your emotions. They also provide more actionable strategies for separating facts from assumptions in your initial story: For example, they recommend watching for emotionally charged terms—for example, “she scowled at me” might sound like a fact, but “scowled” is a word that expresses judgment.

Then they, like Brown, recommend speaking with the people involved, and they present an acronym for helping you do so: STATE. Share your facts, starting with the least controversial. Tell your story, explaining what you’re beginning to conclude. Ask for others’ paths, encouraging others to tell their facts and stories. Talk tentatively, stating your story as opinion, not fact. Encourage testing; in other words, proactively seek opposing views to test your theory against additional information.

Question Initial Stories in Turbulent Times

Brown adds that it’s especially important to lead your team in questioning and talking through their initial stories in times of change or uncertainty in your organization, when rumors are prevalent. People tend to believe their stories and retell them as truth, breeding insecurity and anxiety. Just think how easy it is for “There will probably be massive layoffs at the end of the summer, I can feel it” to become twisted into, “There will be massive layoffs in August.”

Brown explains that you can stop these stories by offering as much information about the situation as possible and speaking to your team with transparency to separate fact from imagination—before rumors abound. Addressing your team’s stories now will take some extra time, but it’ll also save you from wasting your time on fixing defensive behaviors down the road.

How to Talk to Your Teams About Their Initial Stories When Working Remotely

If you’re working in a virtual or hybrid team during a time of uncertainty in your organization, don’t try to discuss your team members’ initial stories via email or chat; talk to them live. Experts argue that easily accessible leaders are key to promoting transparency on (partly) remote teams: Your in-person and remote employees should both have equal opportunity to ask you questions, and making people email you adds a barrier to entry that’s not present when you’re talking in person. Additionally, having this conversation via video chat improves the chances that you’ll notice that something is wrong even if your team member isn’t explicit about her concerns: The vast majority of our communication comes from factors other than the words we speak, like our gestures.

Introduction: Why Brave Leadership Matters...and What’s Getting In Its Way

We’re living in a rapidly-changing world that demands constant innovation and creativity from organizations. But there are four errors that organization leaders make that get in the way of creativity and innovation.

Error #1: Trying to engineer vulnerability and uncertainty out of the workplace

By refusing to allow the risks and uncertainty in their workplaces, leaders create work cultures where team members don’t know how to control their natural emotional reactions to uncertainty and failure. Instead, their team members are driven by their emotions toward defensive behaviors that hold them back, such as perfectionism, criticism, and a refusal to take responsibility for their mistakes.

Furthermore, many leaders use unclear or untrue language in tough conversations in a bid to protect themselves from the negative emotions that might be sparked by honesty. By doing this, leaders create work cultures that are void of the honest and productive feedback that allows team members to improve themselves.

Error #2: Not establishing clear values

When a leader doesn’t spend time clarifying an organization’s values, those values will be too ambiguous to be modeled or evaluated. The leader will waste time trying to “wrong” behaviors that don’t align with their vision for the organization, without being able to pinpoint why the behavior is wrong or what behavior would be considered “right.”

Additionally, organization members should be able to lean on their values when faced with a tough decision. Wishy-washy values aren’t strong enough to act as a guide, and organization members risk listening to whatever opinion is loudest, or doing what is easiest over what is right.

Error #3: Not building connection or trust in their organization

When there’s no culture of trust in a workplace, team members hold back from expressing new ideas for fear of being ridiculed by their colleagues or punished for going against the status quo. This lack of trust extends to the way team members recover from failure and shame as well—they don’t talk about or work through tough situations if they don’t feel that their colleagues will respond with empathy and support. Instead, they let the shame fester under the surface, manifesting in toxic defensive behaviors.

Error #4: Not preparing their team members to deal with failure

When team members aren’t prepared to fail, they don’t respond productively to failure—they react emotionally. This drives problematic behaviors such as covering up mistakes instead of talking about and learning from them, or blaming one another for failures and setbacks instead of holding themselves accountable. With teams that can’t handle failure, leaders waste their time on reassurance and fixing defensive behaviors.

The way to combat all four of these errors and build a thriving organization is brave leadership—leadership that allows for risk and failure, and engages with feelings of uncertainty and fear. Brave leadership is necessary because it fosters courageous work cultures, where employees take risks and learn from their failures—which is crucial for innovation. Developing these skills and teaching them to your team is hard, uncomfortable work—but you’ll gain a culture where members act with integrity, share ideas without fear of judgment, respond to failure productively, and will take the risks necessary to innovation.

We’ll walk through the four courage-building skills that all brave leaders should practice: facing vulnerability (Chapters 1.1-1.5), choosing and practicing values (Chapter 2), building trust (Chapter 3), and developing failure resilience (Chapter 4).

Chapter 1.1: What Vulnerability Is (And Isn’t)

Vulnerability is exposure to the risk of failure, to situations with uncertain outcomes, or to the possibility of emotional harm. Facing your vulnerability is at the base of brave leadership: it’s only in meeting vulnerability head-on that you can master your response to the fear and uncertainty that come along with it. Before you can face your vulnerability, you need to understand what it looks like. There are six widely-held myths about what vulnerability is, and how you should react to it.

Myth #1: Being vulnerable means being weak

While vulnerability does stem from situations that make you feel afraid, it’s important to understand that vulnerability isn’t fear. Rather, it’s recognizing your feelings of fear and knowing that something out of your control may happen, and being brave enough to push on anyway. It’s not weak—walking into, rather than avoiding, tough situations or the potential for failure takes an immense amount of courage.

Myth #2: Vulnerability isn’t for me

Life is naturally full of experiences that have uncertain outcomes and expose you to the risk of failure—it’s not possible to have a work culture void of vulnerability. No matter what measures you take, vulnerability will naturally happen to you and your team members. Choosing not to engage with this vulnerability doesn’t signal bravery or control. Rather, it signals that your work culture is based in hiding from and being driven by emotions.

A work culture that doesn’t “do” vulnerability reacts to failure with fear and anger, in a way that doesn’t truly represent their values. On the other hand, work cultures with brave leadership that encourages engagement with the emotions of vulnerability react to failure with productive self-awareness that’s aligned with the organization’s values.

Myth #3: I don’t need anyone

Asking for help, sharing ideas, and connecting with others can be frightening because you can’t control how your need for help or your ideas are perceived, or you may be rejected. You can avoid this vulnerability only if you never connect with or depend on anyone, but of course, this isn’t a plausible choice in an innovative work culture where collaboration is crucial. Humans are social by nature—we depend on the ability to communicate, work together, and depend on one another in order to thrive. Fearing, and subsequently refusing, this collaborative part of our nature can cause innovative cultures to collapse.

Myth #4: I can have vulnerability without uncertainty

Some leaders refuse to allow vulnerability in their workplace, because they misunderstand the difference between systemic vulnerability and relational vulnerability.

Systemic vulnerability is unwelcome—it refers to flaws or instability in your organization’s systems. In this context, it makes sense to mitigate risks and reduce opportunities for uncertainty. On the other hand, relational vulnerability refers to the vulnerability of people: the risk and uncertainty that comes with trying something new, or the possibility of emotional exposure in tough conversations. This is a welcome type of vulnerability that helps team members grow.

Some leaders, especially in fields where uncertainty or instability signals failure, find it difficult to invite vulnerability into the workplace, or try to engineer a type of vulnerability that doesn’t involve uncertainty—suggesting an app to guide tough conversations, for example. However, it’s important to practice relational vulnerability, in all its uncertainty and need for courage, to bolster your team members’ growth, learning, and innovation.

Myth #5: Trust must happen before vulnerability can

It’s widely thought that you need to trust someone deeply before you can be vulnerable with them. In reality, vulnerability and trust are a constant exchange—you do need to trust someone to be vulnerable with them, but you also need to be vulnerable in order to build trust. It’s important to realize that this exchange doesn’t happen suddenly, with a grand gesture of trustworthiness. Trust-building happens in a long, slow sequence of small moments where it’s clear that people are truly listening to and connecting with you.

Every interaction you have with someone is the opportunity for a trust-building moment if you recognize it and respond accordingly. When someone is vulnerable with you, and you choose to turn toward their vulnerability—that is, listen to and support them—you earn their trust and the right to share your vulnerability with them. Imagine that you see your colleague is upset after a meeting. You can build trust with her by asking what’s wrong, listening to her, and asking questions to help work through the problem together.

However, it’s just as easy to destroy trust by turning away from the vulnerability someone is offering you—when you choose to ignore or criticize them, you stop the trust-building exchange in its tracks. Imagine that your upset colleague had asked to talk to you about her tough meeting, but you chose to go back to your emails, saying you were too busy to listen. It’s not likely she’ll trust you again with a moment of vulnerability.

Myth #6: Practicing vulnerability means spilling everything

Practicing vulnerability as a leader does not mean spilling all your emotions and personal details. Instead, brave leaders practice vulnerability by acknowledging the uncertainty or risk of a situation, talking openly about the emotions tied to it, and creating a space where your team members feel safe discussing it. This might look like, “Our organization is undergoing a lot of changes. It’s normal to be anxious during this time—I’m right there with you. What questions or concerns do you have? How can I support you through this?”

Asking for input from your team members, thereby building a safe space for discussion, is crucial to encouraging vulnerability among your team. Without fear of backlash, they’re more likely to ask questions, propose new ideas, or admit mistakes. Be sure that your team members fully understand what the objectives of this space are.

In this process of speaking openly and building a safe space, be careful not to practice fake vulnerability—this type of vulnerability shows up in two ways: manipulative oversharing and insincerity.

Manipulative oversharing happens when a leader expresses too much personal emotion and information. This is usually fueled by selfish underlying intentions—self-protective reasons they’re sharing outside the bounds of what’s smart and effective to share—and underlying expectations—the desired (but unlikely) outcome, usually sympathy.

Imagine that a shop is going through some tough months, and the staff is concerned about their hours being cut. The shop owner decides to get really vulnerable with them, saying, “I’m trying my best and working around the clock but we’re hemorrhaging money, I don’t know how I’ll make rent next month, and I’m losing sleep every night over it. We really need to stick together for support at this time.” The underlying intention of her oversharing is to convince her team that she’s a good person trying her best, and her expectation is that they’ll sympathize with her instead of shaming or judging her. In reality, her oversharing will likely cause her team to stop trusting her, panic, and start looking for new jobs.

Manipulative oversharing can be avoided by setting boundaries: while the shop owner’s oversharing is okay with a mentor with whom she’s established a fully-honest relationship, her team should hear, “It’s been a slow few months and I know it’s causing anxiety. I’m working on a plan to get us through this. I’m happy to hear any input or questions you have.”

The second form of fake vulnerability is insincerity. Insincerity is asking for input without building space for discussion. It looks like asking how you can support your team without giving them time to answer; ignoring your team’s ideas, getting defensive, or shooting down ideas that you don’t agree with; and saying you accept your team’s suggestions and then complaining about them later to a colleague. Practicing insincere vulnerability breeds anxiety and distrust among your team members, who will hold back from speaking about their concerns for fear of being ridiculed or criticized.

In the following four chapters, we’ll discuss how facing vulnerability impacts four crucial leadership skills: having hard conversations (Chapter 1.2), lowering your defenses (1.3), accepting shame and showing empathy (1.4), and developing confidence and curiosity (1.5).

Exercise: Bring Vulnerability to Your Workplace

As a leader, you need to debunk the myths of vulnerability in your workplace—and be the first one to model how vulnerability can be allowed.

Chapter 1.2: Having the Courage to Start Hard Conversations

Leadership naturally demands that you engage in difficult conversations where you give and receive feedback, or bring up emotional issues that your team is facing. These conversations often stir up fear and uncertainty—you can’t control how they will go, and often they depend on a great deal of emotional exposure.

It’s tempting to shy away from the uncertainty of these conversations. Facing vulnerability, however, grants you the courage to approach these conversations with honesty and clarity—your guiding principle in difficult conversations should be that it’s kind to be clear, and unkind to be unclear. This ensures productive conversations that foster learning and give you necessary insight to best serve your team.

First, we’ll look at how this principle should guide feedback sessions, and then we’ll discuss how you can depend on clarity of language to open conversations about difficult or awkward emotions.

Giving and Receiving Clear Feedback

Often, people give feedback that is polite, but dishonest. Their argument is that giving polite feedback is the nice thing to do—but the real motive isn’t so altruistic. In fact, people give polite feedback because it’s easier and more comfortable for them. Dishonesty allows them to avoid the discomfort of telling someone they’re not performing to their standards.

Dishonest, polite feedback is unkind because it’s unfair—the recipient receives no indication that they need to improve, yet they’re held accountable for their lack of improvement. Moreover, it wastes time and creates frustration as the same unaddressed problems continue to crop up.

The natural remedy to this issue is to start giving direct, honest feedback. Be aware that doing so might be a difficult adjustment to your team if you’ve created a culture where polite but dishonest feedback is the norm. To avoid having your team shut down or get defensive in response to this new type of feedback, volunteer yourself as the first honest feedback recipient.

Go into this first feedback session with two goals in mind: to model a thoughtful response to hard feedback and demonstrate honest feedback’s productive outcome. You can open the feedback session by asking your team how you can better lead them. They will likely default to “nice and polite,” so be prepared to suggest areas of improvement and ask about their experiences working with you—ask for specifics, and keep pushing until you receive an honest answer.

Once you have feedback to work with, your session should have four parts: 1) be curious, 2) take a step back, 3) question your motives, and 4) share your thoughts.

  1. Be curious. It’s easy to get defensive and push back or shut down when hearing about your problems. Resist this instinct by asking for clarification.
  2. Take a step back. Ask for time away to think about what’s been said, consider how it’s made you feel, and figure out what the root of the issue might be. Be careful in how you present your need for some space. Many people speed through the discomfort of negative feedback, wrapping up the conversation with a vague and dismissive “Okay, I’ll think about that.” Knowing this, you can avoid sending a dismissive message by clarifying that you want time to think through the problem so you can come back and continue the conversation with your findings.
  3. Question your motives. Ask yourself what could be motivating your behavior—what is the real problem?
  4. Share your thoughts. Come back to the team and share your thoughts. This is an especially vulnerable step—it’s difficult to expose the emotional issues causing your behavior. It would be much easier and more comfortable to put the blame elsewhere, but your brave leadership role is to be as honest as possible. Exposing the root of the problem allows your team to help you think of productive solutions.

Example: Feedback on Time Management Skills

Your team tells you that you lack time management skills and that you keep asking your team to accomplish projects on impossible deadlines. You ask them to tell you more about how your tight deadlines affect them and their work, and take notes. You thank them and ask for a follow-up meeting the next day after you’ve had some time to think. In your follow-up meeting, you share your insight: when you set tight deadlines, you are usually feeling anxiety that a competitor will “do it first,” and you are thinking of multiple projects and deadlines that you haven’t communicated to your team. The problem isn’t time management—it’s anxiety and lack of communication. Your team comes up with a solution—when new projects are put on the table, everyone writes down how long they think the project will take and how it should be prioritized alongside current projects. They then share their estimates as a group and create deadlines and priorities that work for everyone.

Talking About Difficult Feelings

Beyond honest conversations surrounding feedback, brave leaders need to engage in honest conversations surrounding difficult or awkward emotions. These conversations are necessary to a thriving work culture—if you don’t invest time in them, you will end up wasting time addressing problematic behaviors that team members rely on to cover up their difficult emotions.

These conversations require the vulnerability of using the right language. In workplaces, language is usually sanitized and disconnected from the very real emotions that team members experience and need to work through

Brave leadership doesn’t allow team members to fall back on describing “easy” emotions to avoid their true, difficult emotions. Brave leadership puts the correct language to the feeling, and it allows space for discussion. This is much easier said than done—using the right language can make people feel very emotionally exposed, which is uncomfortable for both parties.

Once you open up these honest conversations around emotions, you need to be brave enough to stay in the discomfort that comes with them. You can best do this by simply listening, resisting the temptation to talk away the discomfort or come up with answers. By allowing space and silence in the conversation, you let people discover the true core of their emotions and behaviors by themselves.

For example, Colonel Dede Halfhill of the Air Force regularly opens honest conversations with her airmen about their emotions. She started the practice years ago, when her airmen started asking to slow down operations because they were tired. In response, she told them about a study she’d read that showed that high levels of loneliness often manifest as exhaustion. This prompted an honest discussion about loneliness in the Air Force and her methods of support. Consequently, Halfhill stopped giving isolated time off for exhaustion and started focusing on connection and inclusion.

Honest conversations are difficult, but crucial to serving your team members and getting ahead of the emotions that often manifest in defensive behaviors that are toxic to innovative cultures.

Exercise: Practice Giving Clear Feedback

Being clear in your feedback about your expectations and intentions is essential to avoiding more problems down the line.

Exercise: Open Up Tough Conversations

As a leader, you need to be willing to address tough emotional issues with your team members and open up a conversation about them.

Chapter 1.3: Lowering Your Defenses

Often, leaders try to engineer vulnerability out of their work cultures because they believe that it will make their team members more efficient and less susceptible to emotions. In fact, when organization members aren’t given the opportunity to face their vulnerability and think through their emotions, they allow their ego to take control and become more susceptible to emotional reactivity. The ego will adopt any behavior that might protect it from being bruised by negative emotions such as embarrassment or shame.

Leaders and their team members usually resort to one or several of 16 defensive behaviors—in this chapter, we’ll walk through how these behaviors present themselves, how they hold back your team, and how brave leaders take steps to discourage them and solve their sources.

Behaviors to Avoid Difficult Emotions

Defense #1: Numbing Difficult Feelings

When prevented from engaging with negative emotions, team members may escape their feelings with numbing agents such as drinking, shopping, over-scheduling, gambling, and so on. Besides the obvious risk of addiction, this threatens their mental health because it’s not possible to choose which emotions are numbed. Positive emotions are numbed along with the negative.

Brave leaders combat this behavior by regularly checking in with their emotional needs and finding healthy outlets for negative emotions, and teaching their team members how to do the same. This can be taught as a simple shift in thinking: rather than, “How can I make these feelings go away?” have your team members try, “What is the source of how I’m feeling?” This shift replaces the need for a numbing vice with the choice of an appropriate comfort. For example, a team member might feel angry and indulge in a bottle of wine to cope. But if she were to explore the source of the feelings—she’s feeling irritable at the end of a hard day and needs some calming alone time—she can choose a more comforting outlet like putting on some favorite music and cooking a nutritious meal.

Defense #2: Avoiding Difficult and Awkward Situations

People tend to put off difficult or awkward situations—such as asking for a favor or facing a conflict—because the vulnerability of these situations is uncomfortable. It might feel easier to avoid the discomfort, but in the end, this avoidance is mentally exhausting and a waste of time. After all the time and energy spent, the difficult situation still needs to be dealt with.

Brave leaders combat this behavior by showing their team members how to mentally prepare themselves to directly face vulnerable situations. This simply involves taking a moment to ask yourself: “What feelings are driving me to avoidance? What can I control? What do I need to accept is out of my control?” Walking through these questions provides clarity about the situation—the resulting sense of calm, rather than anxiety, makes the situation easier to face. Without this mental preparation, they’ll continue practicing avoidance, but this only leaves them prone to being caught by the situation when they’re emotionally and mentally unprepared for it.

Behaviors to Prove Self-Worth

Defense #3: Overcompensating to Prove Worth

Team members who feel insecure about their value or place within your organization will often overcompensate to prove their worth. Overcompensation can present as the need to be right, or the pursuit of validation rather than self-improvement. Often, overcompensating team members slow down their colleagues by pushing themselves into projects where they’re not needed or their skillset isn’t helpful.

Brave leaders combat this behavior by giving positive feedback to their team members and reminding them of what particular value they bring to the organization. When team members feel secure about their worth, they focus on improving within their unique skill set rather than hustling for everyone’s attention and validation.

Defense #4: Attaching Self-Worth to Productivity

Team members insecure with their inherent value might attach their self-worth to their productivity. They’re too hard-working, never taking a break for anything they deem “unproductive,” such as vacations or hobbies. This over-productivity is often damaging—our brains require downtime in order to learn new things, exercise creativity and innovation, and simply rest. If a team member is never “off,” she’s putting herself at very high risk for depression, anxiety, or burnout. Furthermore, over-productive attitudes are contagious among colleagues and spur everyone to overwork themselves—leaving you with a team of burnt-out, undercreative people.

Brave leaders combat this behavior by setting healthy boundaries among their team members. Start this process by setting boundaries for yourself, such as, “I won’t reply to emails on the weekend.” These boundaries should be extended to your team members—if you don’t want to receive weekend emails, you shouldn’t be sending them weekend emails. Once you’ve demonstrated your commitment to your boundaries, encourage your team members to make their own.

If you have team members who brag about exhaustion, or working through their time off, be careful not to reward them—this can be obvious, as with praise for hard work, or subtle, as with engaging with their overproductivity and allowing them to work during their time off. Instead, talk to these team members and emphasize your expectation that they prioritize downtime. Explain why downtime is important to them and the organization as a whole, and help them set healthy boundaries.

Defense #5: Suppressing Authenticity to Fit In

In a work culture based on the status quo and “fitting in,” team members might feel that they need to suppress their authentic selves in order to be respected and heard. Naturally, this calls into question the authenticity of their colleagues—who are likely also suppressing their authentic selves—and diminishes trust. Furthermore, a lack of diversity in an organization prevents the discovery of the new perspectives and ideas essential to a thriving innovative culture.

Brave leaders combat this behavior by committing themselves to the inclusion of diverse perspectives. You can start by becoming more aware of your privilege and biases. Ask yourself: “Does everyone on my team look like me? Does everyone have the same background? Is there anyone I overlook in meetings because they’re not the same as everyone else?”

This line of questioning can be tough. It’s hard to see what prejudices you might be unconsciously holding, but you need to rely on your commitment to brave leadership to acknowledge and work against these blind spots. If you find that there are team members whose perspectives and ideas you favor, spend time recognizing the efforts and value of those you tend to overlook.

Defense #6: Looking for Self-Worth Externally

Team members with no sense of self-worth often try to fill the space with power or validation by taking credit for work or ideas that aren’t theirs, comparing themselves to others, and needing to be right all the time. These behaviors inhibit innovation and learning, confidence-building, and the ability to recover from setbacks.

Brave leaders combat this behavior by reminding those team members displaying a lack of self-worth of the unique value they bring to the organization. If you don’t address the self-worth problem directly, your team member will continue holding themselves—and the organization—back by avoiding any risk of failure and trying to prove that they’re never wrong and better than everyone else.

Behaviors to Keep Others at a Distance

Defense #7: The “Kill Or Be Killed” Mentality

Unhealthy work cultures pit team members against one another—in these environments, any show of vulnerability is seen as failure. This mentality is toxic to innovative settings because it’s void of meaningful collaboration and self-improvement, instead focused on gaining approval.

Brave leaders combat this behavior by rewarding those who show vulnerability and collaborate, not compete, with others. You can accomplish this by identifying team members who ask for feedback on their ideas, ask for help from others, and are transparent about their mistakes. Reward these team members with recognition for their commitment to self-improvement—meaningful recognition depends on the team member, but it can look like a shoutout at a meeting, a promotion, or a shift in focus onto more meaningful projects.

Defense #8: Cynicism and Sarcasm

In response to negative emotions, team members might put up a snide, detached, or suspicious front that lets them avoid engagement with these feelings or with other people. This approach of cynicism and sarcasm usually turns work relationships sour, because it stirs up feelings of anger, resentment, and confusion. Other people might distrust them—“What does she really mean when she’s saying ‘great work’?”—or they might become distrusting of others—“My colleague is purposely slowing down this project to make me look bad.”

Brave leaders combat this behavior by rewarding clear communication while refusing to allow or engage with cynicism or sarcasm. With the knowledge that team members usually resort to cynicism and sarcasm when they’re hiding feelings like fear or inadequacy, you can open up an honest conversation with them about the difficult emotions they’re dealing with.

Defense #9: Criticism

Team members who feel inadequate or afraid often criticize others as a way to shift negative attention from themselves onto someone else. Unmitigated criticism is toxic in an innovative culture, because the fear of backlash or ridicule stops team members from contributing ideas or breaking the status quo.

When trying to weed criticism out of your organization, you need to listen carefully—criticism isn’t always obvious. There are two ways that people veil criticism: clinging to the past and the royal “we.”

Brave leaders combat this behavior by counterbalancing criticism with contribution. You can easily achieve a healthy contribution and criticism balance by establishing a new policy stating that team members can’t criticize without offering their own point of view or idea.

Defense #10: Abusing Power Dynamics

Power is not inherently dangerous, but it becomes dangerous when it’s used to protect a higher-ranked minority while disadvantaging the majority. This protection of the minority causes resentment and resistance among the majority. Yet, the cycle never breaks—as members of the disadvantaged minority are promoted to higher levels of power, they begin to feel that they have more value than those at the bottom. They choose to abuse their power to benefit themselves and their perceived higher value.

Brave leadership combats this behavior by reassuring their team members that they all have power, at any level. This stops the abuse of power at higher levels, because people aren’t given the idea that they’re somehow more valuable. It also calms the resentment at lower levels, because people are no longer being disadvantaged by abuse of power, and understand their agency and value in organization. This can be accomplished by reminding team members at all levels that they possess three types of power: power with, power to, and power within.

Behaviors to Avoid Failure & Mistakes

Defense #11: Perfectionism

Team members resort to perfectionism to protect themselves from the embarrassment and shame that come from experiencing failure, being criticized, or not living up to the expectations of others. Perfectionism prevents team members from taking on challenges and risks that foster progress and learning, which are crucial to an innovative culture.

Perfectionism is an ongoing cycle that worsens over time—they try to be perfect, inevitably fail, and conclude that it was because they weren’t perfect enough. As the cycle continues and failures inevitably pile up, the team member takes smaller and smaller risks so that they can achieve perfection every time.

Brave leaders combat this behavior by having open and honest conversations with their teams about the drawbacks of perfectionism, and present the idea of healthy striving. Perfectionism is external and focuses on the perceptions of others—it looks like, “What will people think of me and my work?” On the contrary, healthy striving is internal and focuses on self-improvement—it looks like, “How can I be better?”

Defense #12: Needing to Be Right

Insecure team members might feel that their value lies in being right all the time. This presents as refusal to admit mistakes, rejection of others’ answers, and making up answers instead of saying, “I don’t know.” This behavior pulls down everyone who needs to work with the always-right team member, for several reasons. Firstly, they’re likely to cover up their mistakes, which creates distrust and misinformation. Secondly, their “my way is the only way” mindset leads to poor, ego-based decision making. And thirdly, team members who need to be right are usually in constant conflict with anyone who disagrees with them.

As a leader, it’s possible that you’re exacerbating this problem by valuing certain people as “always right,” which takes away the power of other, less tenured people to contribute diverse ideas. Imagine that someone who’s an expert in their field joins your company. Six months in, she has yet to contribute to a single meeting because your company’s culture dictates that only the ideas and opinions of long-term leaders are valued. You’ve missed out on valuable insight and discussion by creating a culture that discredits new perspectives.

Brave leaders combat this behavior by having an honest conversation with the always-right team member about their issue, and offering suggestions for improvement. For example, you could say, “I appreciate that you always have answers to problems, but I think you should work on asking good questions as well. Developing curiosity and thinking critically is what will help you thrive on this team.”

Furthermore, you should recognize team members who are committed to learning—they ask questions often and admit when they don’t have an immediate answer. By recognition for these behaviors, you can demonstrate to your team that there’s no value in always being right, but rather in continued effort to learn to do things right.

Behaviors in Conflict With Brave Leadership

When identifying defensive behaviors in your organization, don’t forget to look in the mirror. While the first 12 defenses focused on team member behaviors, the next 4 will focus on behaviors that ego-driven leaders are susceptible to.

Defense #13: Refusing to Celebrating Achievements

Joy is wonderful to have, but it can be lost at any moment. Because of joy’s vulnerability, we can feel vaguely threatened by it, and respond by refusing to engage with it—thinking that doing so will protect us from inevitable disappointment or hurt. Refusal to engage with joy usually shows up in two different ways in the workplace:

If your team members never have the opportunity to rest or feel pride in their work, they will quickly become burned out and disengaged from the work.

Brave leaders combat this behavior by acknowledging that something bad might happen or their employees may stop striving, and then choosing to celebrate the achievements of their team anyway. When you recognize your team members’ efforts and achievements regularly and sincerely, they usually don’t become complacent. Instead, recognition increases their engagement and satisfaction with their work.

(Shortform note: To learn more about how recognizing and celebrating your team’s “moments of pride” can boost their engagement and motivation, read our summary of The Power of Moments.)

Defense #14: Controlling Instead of Leading

Leaders that feel insecure about their ability to lead a team often try to wield their power in a controlling manner. There are two main behaviors that controlling leaders resort to:

Brave leaders combat the first controlling behavior by giving their team autonomy and reminding them of the larger purpose of their work. You can do this by sharing your hopes and vision for the organization, and explaining what you’re working toward. Correct your reliance on fear-based motivation by recognizing and rewarding work that’s moving in the right direction, instead of punishing work that’s “wrong.”

Brave leaders combat the second controlling behavior by thoroughly discussing expectations and capabilities with team members. These discussions should have the goal of clarifying exactly what a successfully finished task looks like. This allows you to identify where responsibility and authority might be misaligned, and reassess each person’s responsibilities.

Imagine telling a team member, “I need the ad mockup for the meeting at 4.” If your team member has the space for discussion, they have the opportunity to ask, “What do you need exactly? Just the one mockup?” At this point, you may realize that you actually need two versions of the ad with two different themes, and copy for each—a much different result than you’d originally asked for. Now, your team member knows exactly what needs to be done, and where their lack of authority will get in the way. They say, “To get it done by 4, I’ll need you to tell graphics it’s priority. We’ll also need a short meeting at 2 to approve the images and copy.”

If you’d left the conversation at “I need the ad mockup by 4,” you would have ended up with an incomplete ad mockup, or a result far below your true expectations.

Defense #15: Using Fear and Uncertainty for Control

In times of uncertainty, leaders might weaponize fear to their advantage instead of talking through the emotions with their teams. For example, a leader of a company dealing with financial troubles might use the threat of layoffs to motivate team members to work longer hours for no increased pay. In the short term, fear is a strong motivator, but in the long term, it will manifest as a number of defensive behaviors we've explored, such as numbing, perfectionism, and unmitigated criticism.

Brave leaders combat this behavior by supporting team members through fear and uncertainty without using it to their advantage. As we explored in the myths of vulnerability, you can effectively communicate about uncertainty to your team by acknowledging fear, giving as much information as you can, and creating a space for discussion. This relieves your team, reducing their defensive behaviors, and builds up their trust in you, which is a strong long-term motivator.

Defense #16: Collecting Accolades, Instead of Giving Them Out

In the early stages of your career, it’s okay to keep tabs on the “gold stars” you receive for work well done, or for improving skills. This is useful for discovering your self-worth and knowing what value you bring to the workplace. However, insecure leaders who continue focusing on getting validation even after they move up the ranks are distracted from the goal of leadership. They should be giving out validation and helping team members understand their value.

Brave leaders combat this behavior by committing themselves fully to the work of leadership and the advancement of their team. When you transition into a leadership role, you need to reorganize your priorities. You should no longer be focused on gathering validation for yourself, but rather focused on recognizing the work of your team members, reminding them of their unique skills, and looking for ways to help them reach their potential, such as with networking or work opportunities.

Exercise: Recognize and Combat Defensive Behaviors

Practice spotting defensive behaviors in your organization and taking steps to discourage them.

Chapter 1.4: Accepting Shame & Showing Empathy

Many defensive behaviors in the workplace are, at their core, about avoiding the threat of shame—the feeling that something you’ve done (or not done), a goal you haven’t achieved, or an ideal you didn’t measure up to makes you a flawed person unworthy of connection, love, or belonging.

Shame touches your core, telling you that you deserve failure, are deeply alone, and that your bad actions are not just behaviors, but who you inherently are. It’s sometimes grouped with other negative emotions such as guilt, humiliation, and embarrassment, which are usually short-lived and relatively superficial. However, it’s important to understand how shame differs from these emotions—it’s much more painful and frightening, and therefore much more powerful.

Shame is not the same as guilt. Guilt happens when you act against your values, giving you the feeling that you’ve done something bad. It may be uncomfortable, but it’s usually a valuable learning experience that reminds you of your values, and prompts an apology or behavioral changes. Shame, on the other hand, is the feeling that you are bad and usually doesn’t reveal any sort of learning experience—instead of making changes, you believe that you’re inherently a bad person, incapable of doing better.

Shame is not the same as humiliation. Humiliation is short-lived and externalized—you don’t feel bad about yourself, but rather about how you’ve been treated in a situation. Shame, on the other hand, is deep-rooted and internalized—you feel bad because you believe you are the problem. Imagine you were publicly chastised for missing a deadline. Humiliation would look like, “I didn’t deserve to be called out in front of everyone.” Shame, however, would look like, “I was called out because I am a failure.” Humiliation doesn’t usually feel deserved, but shame always does.

Shame is not the same as embarrassment. Embarrassment is a fleeting emotion that you know is universal. Usually, like falling down the stairs in middle school, it can even be funny in the future. Shame, however, is very lonely—you believe you’re the only person to have experienced it.

Brave leaders recognize the particular power of shame and how easily it drives emotional reactivity, more than any other negative emotion. You can stay ahead of the effects of shame in your work culture by teaching your team how to face the vulnerability of shame and work through it.

Building Shame Resilience

Unfortunately, it’s not possible for innovative cultures to completely resist shame, as it’s a natural byproduct of risk and failure. It’s possible, however, to build shame resilience—the process of feeling, understanding, and overcoming shame. Shame resilience is an essential skill in brave leadership—normalizing and encouraging discussion around shame allows you to consciously work through it and learn from it, instead of letting it unconsciously manifest as defensive, unproductive behaviors.

There are four components to shame resilience: 1) recognizing shame, 2) seeing the big picture, 3) connecting with others, and 4) talking about shame.

How Brave Leaders Let Someone Go

A brave leader acknowledges that the process of letting someone go often comes with a great deal of shame, and tries to diminish the shame of the experience as much as possible. There are several ways that you can accomplish this:

Done well, this conversation grants your employee a dignified exit, and it can keep their feelings of shame to a minimum. However, it’s very easy for leaders to derail this conversation in several ways. When letting an employee go, be careful not to engage in the following behaviors:

Combat Shame With Empathy

If someone practicing shame resilience reaches out to you to talk about shame, it’s important to know how to respond with supportive empathy. This skill is crucial in innovative cultures, because people are more willing to take risks and show vulnerability when they know that they’ll be supported through their struggles.

Effective empathy is not “making things better.” Rather, empathy is seeing the perspective of someone else, and connecting to their emotions about a tough experience. Since you’re connecting to their emotions—not to the experience itself—it doesn’t matter if you’ve gone through the same struggle or not. You just need to have felt the same emotions at some point in your life.

This connection with someone else’s emotions makes empathy a vulnerable choice, because you must connect with those same emotions in yourself, and speak to the person from that place. As can be expected with shame, the emotions you’ll have to call on are painful ones, such as fear, loneliness, or disappointment. It’s incredibly tempting to avoid the potential pain of empathy by spouting off advice or making an attempt to “fix” everything simply—you can resist this temptation by practicing your empathy skills so that you can show up with courage when you need to.

The Five Skills That Create Empathy

Brave leadership depends on five empathy skills to respond to the vulnerability of shame effectively: 1) taking the perspective of others, 2) being nonjudgmental, 3) understanding the other person’s feelings, 4) articulating your understanding of those feelings, and 5) being mindful.

Skill #1: Taking the perspective of others

The first empathy skill is listening to and honoring the perspective and experience of the person speaking to you. In listening to them, your goal is not to see their perspective of the experience—this would require shedding your own background and experiences and taking on their background and experiences. Of course, this isn’t possible. Rather, your goal is to honor their perspective, which means asking questions and understanding that their perspective is their truth, and may differ from your perspective and your truth.

Including and valuing diverse perspectives is necessary to fully understanding who someone is, and seeing how you can successfully connect with their emotions and serve their needs. This step also paves the way for the type of collaboration that spurs innovation and creativity. For example, while working on a new marketing strategy with a team member who has a very different background from you, he might contradict your ideas and say, “Based on my experience, this strategy won’t work with the audience we’re targeting.” While you can’t view the issue from his perspective, you can engage with his vulnerable choice to push back, and ask him why he thinks that, what his experience taught him, and what his approach would be.

Skill #2: Being nonjudgmental

The second empathy skill is being nonjudgmental when someone opens up about their struggle. This is fairly common sense—judgment doesn’t help people open up and name their fears. It only serves to shame them more and causes them to shut down. However, judgmental moments still happen, usually when we feel most vulnerable to our own shame, and try to soothe it with a sense of superiority.

You can diminish your judgmental moments—and increase people’s willingness to reach out to you—by recognizing and examining them. Finding your shame triggers and working through them helps diminish their power and opens up a more receptive, non-judgmental mindset.

Skill #3: Understanding the other person’s feelings and Skill #4: Articulating your understanding of their feelings

When responding to the shame of someone’s struggle, it’s important to practice the third and fourth empathy skills in tandem in order to have a meaningful conversation about it. Most people have great difficulty articulating their feelings accurately, which makes it difficult to work through the emotions of an experience. You need to work with them to land on the exact emotion that you should be connecting with.

You can do this by listening to their experience, and then telling them what you are hearing and understanding to check if you’re on the same emotional page. It’s very possible you won’t get the emotion exactly right on your first try—just think of the subtle differences between anger and disappointment, sadness and frustration, shame and guilt. It can be difficult to suggest an emotion, because getting it wrong and having to try again might feel like you’re screwing up empathy. But to the other person, it demonstrates that you’re trying your best to understand and connect.

In a conversation with a team member, you might put this skill into practice after a tough meeting. You could say, “I’m really sorry for how that presentation went. I know it can be embarrassing. Do you want to talk about it?” This demonstrates that you’re open to talking about the struggle, and are trying to find the right emotion (embarrassment) to connect with. Your team member might respond, “I’m more frustrated than embarrassed. Based on Lisa’s feedback last week, I expected it to go well. I could have made the necessary changes if I’d received more honest feedback.” Knowing that you should connect with frustration opens up a more meaningful conversation that demonstrates to your team member that you care about working through her particular struggle together.

Skill #5: Being mindful

The last empathy skill is being mindful of how you’re engaging with your own emotions so that they don’t prevent you from effectively connecting with the other person’s. Call on them, but be careful not to suppress them or exaggerate them.

If you suppress your emotions, you can’t connect with those emotions in yourself and in the other person, which derails the possibility of meaningful conversation. If you exaggerate your emotions, you’ll become swept up in the negativity of the moment—you can’t support the other person through the emotions if you’re stuck in them yourself.

Even while practicing these five skills, empathy is difficult—everyone’s empathy needs are different, and there’s always the possibility that you will do or say the wrong thing. It’s important to remember that it’s okay to do or say the wrong thing. If you are trying your best to connect, you’ll notice quickly if you mess up and can easily get back on track. Genuine attempts at empathy are evident—even when they don’t go exactly right, the other person will feel supported by your intent.

How Empathy Can Miss the Mark

On the other hand, if you are not truly connected and engaged with the other person’s experience and the vulnerability they’re showing you, it’s obvious and makes people feel unsupported. Be aware of the six ways you might fall into practicing “false empathy:” 1) sympathy, 2) negative reactivity, 3) disappointment, 4) scolding and blame, 5) making it better, and 6) comparative suffering.

  1. Sympathy is when you feel on someone’s behalf, not with them. This makes them feel alone and disconnected—having someone feel sorry for them signals that their emotions have been noticed, yet they’re being left to untangle them alone.
  1. Negative reactivity is when someone tells you their experience and you overreact, telling them how ashamed you’d feel in their place. Suddenly they feel like they should be helping you feel better. Not only are you not supporting them, but you’re taking their support.
  1. Disappointment happens when someone tells you their experience, and you react by expressing disappointment in them. This makes them feel even more shame, and it tells them that they can’t discuss the experience with you, because they’ve let you down in some way.
  1. Scolding and blame happen when someone tells you their experience, and you scold them or find someone to blame. You do this to avoid negative emotions—shifting them onto a culprit instead of engaging with them.
  1. Making it better is when someone tells you their experience and you throw feel-good phrases at them to avoid engaging with their difficult emotions.
  1. Comparative suffering is when someone tells you their experience and you try to make them feel better by one-upping them. This invalidates their feelings and makes their shame into a competition.

Exercise: Build Shame Resilience

Shame is a powerful feeling that can drive you to defensive behaviors if you don’t keep it in check by practicing shame resilience.

Exercise: Practice Empathy Skills

You and your team members can diminish shame and defensive behaviors in your organization by responding to shame with effective empathy.

Chapter 1.5: Developing Confidence and Curiosity

When faced with vulnerable moments or tough decisions, brave leaders depend on their “grounded confidence.” Grounded confidence is confidence firmly rooted in strong values, self-awareness, and curiosity—it’s what allows you as a leader to face your vulnerability instead of running away and hiding behind defensive behaviors. It’s a crucial component to any healthy work culture, but it’s not something that you inherently have. It needs to be developed, in two ways: continually practicing your values and self-awareness, and approaching your work with curiosity.

Continually Practice Your Values and Self-Awareness

The first component—continually practicing your values and self-awareness—is what allows you to think clearly and with integrity when things get hard. Think about how in sports, you practice the same footwork or play over and over again. You do this so you can perform it perfectly every time, even in the heightened pressure of a game. Your body goes through the motions, while your mind focuses on the rest of the field instead of your feet.

Continually practicing your values and self-awareness works the same way—you practice until acting with integrity and avoiding defensive behaviors becomes second nature, even under pressure or in moments of fear. If you’re able to trust yourself to do the right thing—every time, without deliberation—you’ll be able to free up your mind to focus on the overarching goals of your organization.

This continuous practice does not mean that high-pressure, vulnerable moments will become easy. But it does mean that you will have the confidence to walk into these moments in the first place, knowing that your well-practiced values and self-awareness will guide you in acting with integrity, avoiding defensive behaviors and will ensure that you come out the other side having learned something.

Approach Your Work With Curiosity

The second component of grounded confidence—approaching your work with curiosity—grants you the courage to reckon with uncertainty and failure. In situations or decisions where the outcome is uncertain or failure is possible, it’s necessary to let go of your need for control and replace it with curiosity.

Curiosity is what allows you to approach the problem wondering what might happen instead of panicking because you can’t control the outcome. Approaching your work with a curious, “let’s just see what happens” attitude creates valuable learning opportunities—you ask questions and take time to examine the problems and solutions, instead of racing to find any answer that will fit.

Brave leadership based in grounded confidence is especially important in entrepreneurial and innovative settings, where you’re often required to navigate myriad paradoxes. Simultaneously, your position might require you to be optimistic yet extremely cautious, to be ambitious yet sweat the small stuff, to practice humanity while making tough decisions, to practice humility and boldness, and to strive for both speed and quality.

Grounded confidence allows you to handle the tension of these paradoxes and face the vulnerability of making tough, high-pressure decisions. With grounded confidence, you take the time to ask questions and learn as much as you can, and then rely on your values to make the best possible decision, rather than racing for an answer and choosing whatever option seems easiest.

Chapter 2: Choosing and Practicing Your Values

Grounded confidence requires that you have strong values, which makes the second skill of brave leadership, choosing and practicing your values, particularly important. If you don’t have clear values guiding you through vulnerable situations, it’s very easy to make decisions outside of your integrity. Either you let the voices of critics take control and make decisions you don’t necessarily agree with, or you avoid vulnerability by doing what’s most comfortable instead of what’s right.

We’ll discuss the process of clarifying your values and ensuring they’re put into practice, and then we’ll explore how to effectively carry that process into your organization.

Choosing & Practicing Your Values

As a leader, your first step should be to make sure that you’ve clarified your own values—these will be your guide in making tough decisions, taking risks, and showing your team how to face vulnerability. When choosing your values, consider what your innermost self holds most important in life. Your values should be so defined and clear that acting in line with them doesn’t feel like a conscious choice—they’re simply who you are.

The tricky part of choosing your values is that you need to narrow down to just two core values. If you have too many values, they become meaningless feel-good words, rather than principles that guide your behaviors and intent, and that fuel your ability to commit to things you hold important. For example, “family” may not be one of your two values, but “connection” is. Therefore, connection is at the center of how you make decisions about and within your family. Because possible values are so varied—understanding, wealth, gratitude, recognition, career, joy, diversity, growth—it might be easiest for you to first cut down to ten values that you feel are important, and then narrow down to two from there.

(Shortform note: there are many “value lists” online that can help you with exploring the full range of possible values and finding those that you identify with most.)

Be careful to choose values that you truly identify with. Don’t choose your values based on who other people want you to be (“You should work on your patience”), or choose values that have been assigned to you (“I taught you that family is the most important thing”).

Once you’ve chosen your values, make sure you are regularly practicing them. To help with this, you can make a set of guidelines for each of your values. This is a rubric that you can check in with occasionally, to make sure that you are acting with integrity and that your actions represent who you really are. For each value, think:

Before bringing the values conversation to your team members, realize that there’s no separation between your “personal values” and your “professional values”—your values are your innermost guide, regardless of setting. However, it’s possible that your values won’t necessarily be aligned with your organization’s values. If both sides have clarified values, these different value sets can navigate one another, rather than be at odds with one another. For example, your value of “accountability” isn’t the same as your organization’s value of “collaboration,” but by continually holding yourself accountable for mistakes, you make for a healthier collaborative setting.

Choosing & Practicing Your Organization’s Values

Brave leaders bring the values conversation to their organizations for three reasons: clear values establish trust and understanding, they guide the actions and behaviors of team members, and they open up vital conversations about privilege

Firstly, knowing someone’s values gives you a great deal of insight into their motivations and the reasoning behind their decisions. Having this insight establishes stronger connections and trust between team members. For example, if a team member regularly pushes back on your trendy new ideas, it’s easy to assume they don’t trust your judgment. In a conversation about values, they reveal that one of their core values is authenticity—this reveals that they aren’t distrustful, but that they’re focused on ensuring that ideas are brand authentic, not just bandwagoning.

Secondly, defined values of an organization can be translated into behaviors and skills which can be modeled, evaluated, and improved. Without the tangible aspect of behaviors, organization values risk being too nebulous to be actionable—they become meaningless feel-good words.

Translating values into value-supporting behaviors provides clear guidelines of how you expect your team members to work together, make decisions, and show up to their work. Furthermore, they show you who’s on track, who needs help, and who deserves recognition for their integrity. When thinking of behaviors to model your organization’s values, ask yourself:

The third reason for clarifying organization values is that strong values can support innovative organizations in the discussion around privilege. This discussion is usually swept under the rug because people fear saying the wrong thing, but it’s vitally important to understanding the ways in which your organization supports or excludes diverse perspectives. Brave leaders, knowing that their role is to build an organization that supports diverse perspectives, lean into this conversation, depending on their values to push them through the fear and discomfort of saying or doing something wrong.

Clear Values Improve Feedback

Teaching and practicing strong values is especially important for the process of giving or receiving feedback. Often, feedback can be hard to hear and drives you to shut down or act defensively. When you bring your values to the table, however, you can rely on them to direct your emotions and reactions in the more productive direction of gaining insight and figuring out the way forward.

When giving feedback, think about how you want to bring yourself and your values into the conversation. For example, if one of your values is courage, you can enter the conversation with the commitment to be honest and respectful, instead of defaulting to the comfort of polite half-truths. If your second value is teamwork, you might offer to come up with an improvement plan for your team member, rather than leaving them to figure it out alone.

When receiving feedback, it’s helpful to adopt a value-supporting mantra or behavior, such as “I have the courage to at least sit here and listen” (courage), “Paying attention will make me a better teammate” (teamwork), or “I’ll ask questions and fully understand” (curiosity).

These mantras and behaviors ensure that you show up to the conversation in such a way that you can find value in any feedback you receive. This is important because feedback usually doesn’t happen under perfect circumstances. Instead, you’ll usually find yourself in one of three situations: 1) receiving feedback from someone who doesn’t know how to give it, 2) receiving feedback from someone skilled, but whose intentions aren’t clear, or 3) receiving feedback that catches you off-guard.

Exercise: Choose and Practice Organization Values

Identifying value-supporting behaviors makes it easier to teach and evaluate values, and spot opportunities for improvement.

Chapter 3: Building Trust

The third skill of brave leadership—building trust—is essential to innovative cultures, because trust allows you to rely on others and feel that they have your best interests in mind, and to feel comfortable breaking the status quo or suggesting new ideas. However, as essential as this skill is, it’s rarely brought up in discussion. There’s a huge disconnect between how trustworthy you consider yourself and how trustworthy you consider others to be—but this disconnect is never addressed, for fear that doing so will cause an emotional reaction in the “less trustworthy” person.

Brave leaders understand the importance of recognizing the trustworthiness of their team members, and vice versa, so they don’t shy away from having conversations about trust. However, these conversations don’t speak directly to a team member’s trustworthiness, as it’s a touchy topic and usually prompts a defensive response. Instead, brave leaders talk about trust by discussing the behaviors that demonstrate trustworthiness. Attaching behaviors to the concept of trust accomplishes two goals:

Seven Trustworthy Behaviors to Look Out For

If you want to develop your trust in your team members, look out for the trustworthy behaviors they are demonstrating every day. Recall from the first chapter on vulnerability that trust is built in small moments over time, not in grand gestures—trustworthy behaviors come in the form of small, continuous actions. There are seven behaviors that demonstrate trustworthiness:

  1. Setting and respecting boundaries: You set boundaries and say no when it’s necessary, and you ask others about their boundaries when you’re not sure if something is okay or not.
  2. Being reliable: You are aware of your abilities and your limits and clearly express them to others. You stick to your commitments and do what you say you will.
  3. Staying accountable: You don’t cover up your mistakes or blame others for them—you take responsibility, apologize, and make it right.
  4. Keeping confidence: You don’t share information that is not yours to give away. Keep in mind that you don’t need to directly betray someone’s trust in order to destroy their trust in you—if you are constantly spilling information that’s not yours to share, they will be less sure that they can trust you with their own information.
  5. Acting with integrity: You do the right thing, even if it’s not the convenient choice—you stick to your values, even when it’s hard.
  6. Being nonjudgmental: You don’t judge people that come to you to ask for help, and you are respectful of the ideas they put forward.
  7. Being generous with interpretations of others’ intent: You always assume positive intent when interpreting a situation, or the actions and words of team members

Being generous with interpretations of others’ intent is an especially important behavior for leaders to practice, because it forces you to examine how your leadership might be the root of your team members’ untrustworthy behaviors. It’s easy to assume negative intent when a team member doesn’t deliver on a task, doesn’t stick to a commitment, or otherwise falls short. You assume that they don’t care enough, or they’re trying to undermine you, or they’re not right for the task. However, when you approach these situations assuming positive intent—that is, asking yourself, “If they were trying their best, what got in their way?”—you expose a range of more generous reasons behind the problem. This thinking leads you to realize where you failed to set boundaries, gave unclear guidelines, asked a team member to do something outside of their authority, and so on.

The process of assuming positive intent goes a long way toward building trust, in both directions. When you realize your mistake and subsequently set better guidelines, fill in knowledge gaps, or revise your expectations to match your team member’s skill set, you demonstrate that your team member can trust you. They understand that they can speak up when tasked with something they can’t accomplish, that you’ll push them to grow on in a way that aligns with their abilities, and that they won’t be blamed for results out of their control. Additionally, these revised expectations, boundaries, and guidelines will allow your team member to deliver on their tasks reliably, reinstating your trust in their abilities and commitment.

Imagine that you had an intern who didn’t finish an ad mockup in time for your marketing presentation. In response, you quickly assumed she had bad time management skills. However, once you took a step back and assumed that she was trying her best, you realized that your guidelines weren’t clear and she had to run around all day getting answers from different departments. Furthermore, you said “no rush” in your email to her to be polite, and she had no way to know that wasn’t quite true. On the next project, you spend some one-on-one time with her to clarify guidelines, answer questions, and give a hard deadline. With full, clear information she’s able to deliver, on time.

Building Self-Trust

At the base of building trust with others is your trust in yourself—you can’t give to others what you don’t have. It’s important to continually assess and work on building your self-trust, because it’s not static. Self-trust often wavers following failures or mistakes, when it’s natural to call your capabilities into question. In these hard moments, you can maintain your self-trust by reflecting on the seven trustworthy behaviors and identifying moments where you acted in a trustworthy manner. For example, do you usually take responsibility for your mistakes and make them right? Are you great at setting boundaries? Recognizing the ways that you regularly demonstrate trustworthiness goes a long way toward proving to yourself that you’re capable.

It’s possible, in this reflection, that you’ll discover that there are trustworthy behaviors you’re falling short on. You can reestablish self-trust in these areas by working on them in a way that builds trust naturally, through small moments. For example, if you are coming up short on reliability, you can create and complete small, doable tasks. Eventually, you’ll work your way up through bigger and bigger tasks, until you can trust that you’ll be able to consistently deliver on anything you say you'll do.

Exercise: Practice Assuming Positive Intent

You can build trust with your team members by assuming positive intent and rethinking how your actions may be getting in their way.

Chapter 4: Developing Failure Resilience

The fourth courage-building skill is developing failure resilience—that is, the ability to get up, dust yourself off, and move on after something goes wrong. This is an essential skill for leaders to teach, because people are more likely to take risks and try new ideas when they’re confident in their ability to recover from any setback.

Unfortunately, many leaders teach failure resilience after a failure has already happened. Imagine teaching a skydiver how to land once they’ve already hit the ground—you’ll be dealing with a lot of broken bones and a long recovery. In the same way, if you don’t teach your team members how to “land,” you’ll end up wasting time recovering from problematic behaviors—such as covering up mistakes, blaming others, or perfectionism—that are based in the fear of failure. Brave leaders teach the steps of failure resilience from the very beginning of the onboarding process—this normalizes failure, and signals that team members will be supported, not shamed, when (not if) it happens.

Teaching failure resilience is more important now than ever, as millennials and GenZ enter the workforce. These generations are often not well-equipped to handle setbacks, due to being overprotected by their parents. Because their parents focused on paving the road for them, instead of preparing them for the bumpy road, they haven’t been exposed to the risk of failure and are prone to reacting defensively to any failures, real or perceived.

Productive responses to failure require the two components of failure resilience: 1) recognizing and questioning your emotional response to failure, and 2) unraveling the story you create around failure.

Recognizing and Questioning Your Emotional Response

As with shame resilience, the first step of failure resilience is recognizing and questioning your emotional response to failure. It’s not important to know exactly what you’re feeling. You just need to know that your emotions have been triggered in some way. Failure responses can take many forms—physical or mental—and are very specific to you. You might feel generally overwhelmed, or like you have a pit in your stomach. You might feel like crying or find yourself unable to stop replaying a conversation in your head.

If you know your specific failure response, you can identify when it’s happening—this should cue you to take a moment to think about the source of your emotions. What happened? Why are you reacting to it negatively?

This first step of consciously slowing down and thinking through your emotions is vital to a productive failure response. If you don’t have your emotions in check, they’ll drive you to defensive behaviors. Those who recognize and think through their emotions can respond thoughtfully to failure instead of reacting negatively. However, instead of facing their vulnerability and doing the hard work of engaging with their negative emotions, most people choose the easier route of pushing those emotions aside or onto other people.

The Risks of Refusing to Engage with Negative Emotions

If you refuse to slow down and think through your negative emotions, you risk having them manifest in ways that are not aligned with who you are. There are six common ways that emotions are mishandled: 1) blowing up, 2) replacing hurt with anger, 3) numbing, 4) bottling up, 5) over-positivity, and 6) refusal to engage.

  1. Blowing up: Instead of engaging with negative emotions, you keep them bottled up. They build up pressure until a failure triggers you to completely blow up. This destroys the trust of those around you, who are left wondering if you’ll take out the next failure on them, or if you can be trusted with risky ideas.
  2. Replacing hurt with anger: Because it’s much easier to acknowledge external anger than internal hurt, you react to failure with anger, blame, and excuses aimed at those around you.
  3. Numbing: You let your negative emotions drive you to anything that soothes or lets you forget them, such as food, alcohol, or gambling. This is dangerous not only because it can lead to addiction, but also because you can’t choose which emotions you numb—you’ll end up numbing all of them, even the positive ones.
  4. Bottling up: Instead of engaging with your negative emotions, you push them down and let them amass. While this might work in the short term, in the long term this will manifest as anxiety and depression, physical pain, breakdowns, or insomnia.
  5. Over-positivity: You reject negative emotions, instead putting on a show of positivity: “I feel great, everything is fine!” This chips away at trust—if you’re “never” angry, upset, or sad, your team members don’t feel that you’re sincere, and they fear that the cheery façade will blow off at any moment.
  6. Refusal to engage: You try to control your negative emotions by refusing to engage emotionally with others, fearing that you will get “stuck.” Once you engage, you can’t go back and pretend your feelings don’t matter, but you can’t move forward because it might open a bigger mess of emotions. Instead of giving you control, this thinking makes you feel powerless.

Beyond helping you avoid emotional mishandling or a knee-jerk reaction to failure, this moment of sitting with your emotions allows you to create calm, a natural remedy to the anxiety that comes with failure. Getting a handle on this anxiety in the workplace is especially important because unmitigated anxiety is contagious and quickly becomes the driving force behind your team’s behaviors. It usually shows up among team members as overperformance or underperformance. Overperformers micromanage, take over, and get too involved in others’ business, making others anxious about the quality of their own work. On the other hand, underperformers shut down or ask others to take over, adding to others’ workloads and creating anxiety about their abilities.

Brave leaders demonstrate how to slow down emotions and channel it into spreading calm instead of anxiety in stressful moments. Take time to reflect and ask questions, or purposely speak slowly and calmly during emotionally-charged conversations. Once calm has been created, you can successfully move onto the next step of failure resilience—unraveling the story you’ve created about your failure.

Unraveling the Story You Create About Failure

Thinking through the failure and what really happened is important because in response to failure, your brain naturally makes up a story to explain what happened. Unfortunately, this story is almost never true—instead, it’s pieced together by incomplete information, and usually concludes with a worst-case scenario.

It’s very hard to resist piecing together incomplete information to make a story, because patterns and connections coming together gives your brain a jolt of dopamine. You’re wired to look for and invent connections and patterns in the absence of complete information. Imagine that a colleague spoke to you curtly. You’d likely immediately think, “Jane is being short with me today, I must have done something to bother her.” Your brain invented a connection between your actions and Jane’s tone—whereas if you’d gotten full information you would have known that she’s exhausted because her daughter was up all night, and her tone wasn’t intentional.

These stories usually conclude with a worst-case scenario because doing so gives you the opportunity to preemptively protect yourself. Imagine your boss emails you, “We need to talk.” You think he’s upset about a report you turned in late and is going to yell at you or even fire you, so you avoid speaking to him all day. It turns out he just wanted to talk about the new intern’s performance. By protecting yourself against the imagined worst-case scenario, you’ve wasted the day harboring anxiety and avoiding a meeting.

Handling Your Own Bad First Drafts

In order to stop your brain’s story—the “bad first draft”—from driving unproductive behaviors, you need to look at it objectively with the goal of unraveling it. First, you need to question the story you’re telling yourself, because it’s built from your insecurities and biases rather than from facts. When examining your bad first draft, you should question what you know about yourself, the other person in the story, and your hidden emotions.

Secondly, you need to talk about your bad first draft in order to reveal the holes in your logic. In this step, it’s helpful to use the phrase, “The story I’m telling myself…” This lets you express your feelings while inviting the other person to tell their side of the story. This step untangles the story, leaving just the truth—either your failure is imagined or exaggerated, or it becomes a concrete problem you can now address.

For example, you suggest an idea in a meeting and notice that your colleague Anne looked at another colleague before rejecting your idea. You assume they’ve been talking about you behind your back, and think your ideas are stupid and not worth discussing in meetings. After the meeting, you say to Anne, “You looked at Cheryl before you said no to my idea. The story I’m telling myself here is that you two have been discussing my ideas and don’t think they’re worth your time.” Her response will probably take one of two forms:

Handling Your Team’s Bad First Drafts

Bad first drafts are damaging enough in personal failures, but they become worse in the workplace. Bad first drafts spread easily in work environments, where people tend to believe their own stories and retell them as truth. These stories warp over time, and they breed insecurity and uncertainty. Just think of how easily “There will probably be massive layoffs at the end of the summer. No one told me but I can just feel it” can be repeated and warped into, “There will be massive layoffs in August.”

A brave leader recognizes that bad storytelling is more likely in times of uncertainty, change, and failure and gets ahead of it. You can accomplish this by inviting your team members to share their bad first drafts with you and with one another. This is most effectively done aloud—when incomplete information and worst-case scenarios are expressed, their missing logic becomes apparent.

Hearing your team’s stories and working with them to separate fact from fiction is an opportunity for you to improve your communication style moving forward. This exercise exposes where you’ve left information gaps in which imaginations and insecurities were able to run wild. Moving forward, you’re likely to continually speak to your team with transparency and give as much information as you can, in order to avoid further bad first drafts.

This exercise is also valuable because it presents the opportunity to name and grapple with the problem itself, instead of with all the misinformation around it. Instead of dealing with everyone’s fears of layoffs, you can simply say, “It’s true that our organization will undergo a lot of changes this summer, and it’s normal to be anxious. Currently, there are no layoffs planned and I will keep you updated if that changes.”

While this process of untangling bad first drafts will take some extra time on your part, recall that not spending a bit of time addressing your team’s stories now will result in a lot of wasted time fixing defensive behaviors in the future.

Using the Courage Toolbox

When you lean into all four courage-building skills—facing vulnerability, choosing and practicing values, building trust, and developing failure resilience—you gain control over how difficult situations affect you and the members of your team. The four courage-building skills develop your ability to approach risk and failure productively, instead of reacting to them defensively and falling into behaviors that hold you back from the creativity, collaboration, and ideas that are crucial to keeping up with today’s demand for innovation.

Exercise: Examine Your Bad First Draft

Practice the process of unraveling a bad first draft in order to separate the facts of a situation from your insecurities and biases.