Lead from the Outside

Key Concepts

Success requires understanding why you want something and overcoming fear

“Inevitably, wherever I speak, I get the question ‘How do you do it?’ But I think the most important question is this one: ‘How do I banish doubts and get out of my own way?’” (p. xxii)

“Whether we come from working-class neighborhoods or grow up comfortably middle-class, minorities rarely come of age explicitly thinking about what we want and how to get it.” (p. 3)

“What holds us back is not scope. It’s fear.” (p. 4)

“When I work with young people and others seeking leadership positions, they are primed to jump to the third question, to the how of it, without understanding the what or the why. Some pick a place they want to land or a title they like and then expect teleportation. It may sound corny, but so many of us forget that finding and fulfilling ambition is truly a journey, and one that does not come with a map or GPS, especially for those of us on the outside looking to get in.” (p. 6)

“Ambition means pushing past simply what we are good at. The goal is to stretch ourselves, to explore our potential, even when we know we won’t be first or the best. I sometimes advise people to watch what they fear, what makes them most nervous or feel the most self-protective—sometimes fear masks ambition. And unmasking it can unleash your drive.” (p. 9)

“When you understand the roots of your dreams, you will have deeper insight into why you want what you want. You’ll be able to either strengthen your resolve or clarify if the target you’ve chosen is the right one. What you want to do and why you want to do it should align.” (p. 15)

“When you decide what you want and why you want it, take action immediately. Do not wait for an invitation to act. I promise you, the letter is not in the mail.” (p. 25)

Fear is even more difficult for women and minorities

“Fear is a paralyzing force that twists deep in the gut, churning out anxiety and reasons not to act. Its seductive logic convinces us that now is not our time and winning is not our right. Worse, fear takes on a numbing familiarity, becoming as automatic as brushing our teeth or checking text messages.” (p. 29)

“Fear is real, insidious, and damaging. But it can be defeated if we are willing to name it, own it, and use it.” (p. 32)

“A deep apprehension for many of us is the stereotype threat: the idea that we will always be judged by the worst example of someone in our community.” (p. 33)

“The corollary to the stereotype threat is what I call the authenticity conundrum. Sometimes, our anxiety stems from worry about how our minority status lumps us in with everyone else, erasing our individuality and raising the question: how do we retain a sense of identity without abandoning the true similarities shared with our kindred groups?” (p. 33)

“Navigating power is difficult enough without adding the dimensions of otherness to the mix, but that’s our reality. Traditionally, only white men operate wholly as individuals, each person’s actions attributable to him alone. For everyone else—and I do mean everyone else—we operate as part of a reductive collective.” (p. 36)

“Embracing your authentic self means being clear about how you wish to be seen. This doesn’t mean feigning a personality that is artificial and then cutting loose at home. It means bringing forth who we really are while being acutely aware of our surroundings.” (p. 44)

Information and access can come from unlikely sources

“Confronting issues of access requires that you know where to look for the work-arounds or how to create your own. The second part, entry, means discovering the passwords to get inside.” (p. 59)

“To develop the right connections, the most astute leaders look outside the C-suite. For those of us who do not have strong backers in upper echelons of power, unusual allies can be nearly as useful for identifying opportunities and navigating our way to progress.” (p. 68)

“One key approach is to cultivate relationships with those who have information and are typically ignored. For example, I am always genuinely engaged with support staff wherever I work.” (p. 68)

Humility can hold us back

“Too many of us, paradoxically, use the illusion of humbleness to keep ourselves down. The truth is that what we may think of as humility often disguises an embarrassment about ambition and a lack of self-confidence. We avoid taking advantage of opportunities because we wrongly believe that type of success is not for us. Real humility says, ‘I want something, but I don’t believe that makes me better than someone else.’ Anything else is self-doubt displayed as self-effacement and signals, ‘I don’t believe I’m equal to the other person who wants what I want.’” (p. 71)

“Real humility, on the other hand, is a deep anchor that connects us to our sense of self and pushes us to try more, try harder. Real humility says that we are grateful for the opportunities we’ve had. And we’ve also done our best to make the most of each moment, accomplished a lot, and will continue to do so.” (p. 72)

Rather than having just one mentor, cultivate a network of mentors, including peers, that have situational value 

“I don’t have traditional mentors. Instead, I have curated support, training, and advice from an array of alliances, advisers, and friends: an à la carte approach designed for maximum input and flexibility, for a range of circumstances that can defy the conventional wisdom of success.” (p. 82)

“Before looking for a mentor, you must first verify that you are a person worth the investment of time and energy you seek, which can be a daunting task.” (p. 83)

“I am a strong proponent of the situational mentor—a person who serves a temporary role or has a specific function, like helping negotiate salary increases or promotions.” (p. 85)

“An additional dimension for minorities is that this can mean finding two or more for a single issue because navigating the challenges of diversity requires having an ally who understands intimately what we face, but we also need supporters who know what the majority thinks.” (p. 85)

“We ignore peer mentorship to our detriment, but the mutual benefit outweighs any concerns, as these are often the allies who best understand your current circumstances.” (p. 89)

“A good mentorship network has a number of advisers with specific profiles.” (p. 94)

Success requires being bold and accepting the risk of failture that comes from that

“A central tenet to success is to show up—again and again and again—to take an alternate approach, and keep at it until it works. And when we show up, act boldly, and practice the best ways to be wrong, we fail forward. No matter where we end up, we’ve grown from where we began.” (p. 133)

“To find boldness requires active discomfort: doing that which forces you beyond your bright lines.” (p. 137)

“Boldness lies not simply in having the thought but in claiming ownership, accepting responsibility for moving it forward, and then dealing with the consequences. Prepare to win, but also prepare to fail, always using boldness as your guide.” (p. 141)

Power mapping

“Instead, I rely on two approaches: first, I distinguish my idea of a win from that of the ones in power, and second, I locate who can help me achieve my objectives, often through an activity known as power mapping.” (p. 166)

“The concept of power mapping began in social justice circles with the goal of identifying who had control or influence, understanding their relationships to others, and then targeting them to promote social change. I have developed my own approach to a personal power map, where I lay out the problems I want to fix, pinpointing who can help, who can influence, and how I can get the work done.” (p. 166)

“Given the scope of the issues we face, too often we wrongly map out power by assuming the right leader is the one with the most brilliant mind, with the most unique approach, who can go it alone. Moreover, as minorities, we think that to be valued, we must take all the credit and be the author of every solution. I assure you, this thinking is wrong. The best ideas and the best policies are typically collaborative, and those that succeed are the product of a community.” (p. 169)

POWER MAPPING (pp. 173-4)

1. “Identify your problem or goal: What are you trying to accomplish? Be as specific as possible but clear and to the point.”

2. “Identify the key decision makers related to that goal—by title or position: Who can help you? Who can stop you? Who should be part of the process?”

3. “Map the relationships: If you have a relationship with the person, identify how close you are and if you can directly contact him or her.”

4. “Reach out to targets: Make contact with your targets. Discuss your problem and solicit advice or concerns.”

5. “Make your plan: Collect your feedback and revise your names from step 1. Determine if you can sway anyone opposed or if you actually require the support. Then set out your action steps for how to move forward and what your asks will be.”

Work-Life Jenga

“I reject the idea of work-life balance. It’s worse than a myth. The phrase is a bald-faced lie, designed to hang over the human psyche like the Sword of Damocles.” (p. 175)

“Instead, I believe in Work-Life Jenga.” (p. 175)

“So too, in Work-Life Jenga, the expectation is not one of balance; it’s one of strategy and making the best of each move, one block at a time.” (p. 175)

“Letting go of the finite distinctions and the moral judgments we hear beneath our choices clears the way to allow us to set priorities without condemnation.” (p. 179)

“Doing a job another person can do, particularly better, is a waste of a precious resource. So, before you jump in with both feet, check if you are absolutely necessary to get the work done. Regardless of the task or which category it falls into, the analysis is the same. Are you an essential element for success? If so, go all in. If not, go away.” (p. 191)

“Women, especially black women, are notoriously bad at giving sufficient attention to our need for relaxation and respite from the daily grind of our obligations.” (p. 193)

Quotables

“Greatness demands purpose—in the face of upended expectations and extreme setbacks, even more so. I have faced the toughest loss I can imagine, and I know I will lose again and again. But I will never fail to try.” (p. ix)

“Leadership stands at the crux of how we get to power, and it demands the willingness to go first, to take responsibility as well as hold authority, to help others get where they need to go. I’ve seen leaders emerge out of nowhere in moments of great turmoil. But more often, a leader evolves from a good person who is willing to make hard choices and handle the consequences.” (p. xxi)

“Logic is a seductive excuse for setting low expectations. Its cool, rational precision urges you to believe that it makes sense to limit yourself. And when your goal means you’ll be the first, or one of the few, as I desired, logic tells you that if it were possible, someone else would have done it by now.” (p. 14)

“If you can walk away for days, weeks, or years at a time, it is not an ambition—it’s a wish. Wishes feel good and rarely come true. Ambition, on the other hand, fuels your days and refuses to be ignored. It challenges your sense of self and fulfills your sense of wonder. So pay attention.” (p. 25)

“At a black women’s college, I pretended to be more social, more stylish than I was—driven as much by internalized racism as any societal pressures from my new community. At Yale and at the law firm where I subsequently worked, I pretended mannerisms that I copied from those who’d grown up with privilege, hoping that imitation would become reality. But buying pricey purses and scoffing at foods I’d never eaten failed to change the fact that I was different, and pretending otherwise was a waste of time.” (p. 37)

“The myth of self-made success, or of bold action rewarded for its merits, may work in certain circles, but we’re not often included in its penumbra. Self-made is a misnomer, a stand-in for a more complex narrative that includes the ability to work for no pay, to borrow from friends and family, to experiment and fail without falling too far. This is the comfort of starting on second or third base, thanks to the benefit of family wealth, or the presumption of qualification because of race or gender or background.” (p. 55)

“When we doubt ourselves into inaction, that paralysis becomes a habit.” (p. 73)

“For that reason, I have a regular habit of asking a small group of trusted friends to perform an informal 360-degree evaluation of me. Because each knows me in a different way, I learn more about how I am viewed in separate facets of my life. A word of warning, though. Brutal honesty is not for everyone. Still, having occasional insight is essential to self-improvement and to progress.” (p. 76)

“Fundamentally, the responsibility is on you, as the mentee, to create the mentorship that you want and manage expectations, especially your own.” (p. 96)

“Learning about the finances of a company or an organization is like learning a secret code. The ones who know how to effectively manage budgets and raise funds for projects are usually the ones calling the shots.” (p. 117)

“While the self-help and business books are rife with discussions of leadership, the bald conversation of gaining power—especially for those who rarely hold it—is unusual. As a result, too often, we in the minority miss opportunities because we don’t know what we’re looking at or looking for. Minority leaders do not have the luxury of traditional power, which comes with experience, access, and information. But when we understand how power works and how we can fight back and gain some for ourselves, we can rewrite the rules.” (p. 154)

“Power is directly tied to winning, and for those of us on the outside, the definition of winning must be adaptable to the circumstances.” (p. 165)

“From the tragic to the common to the extraordinary, life refuses to be divvied up into careful slices of time. No technology can manage to overcome the realities of reality.” (p. 178)

“Work-Life Jenga gives us permission to be leaders, to be aggressive, and to be human.” (p. 195)

“For all of us, even me, we have to consistently remember that the game is stacked, but if we can unlock the cheat codes, we can play to win. We can take power.” (p. 201)

“There’s a colloquialism I’ve embraced: let your haters be your motivators.” (p. 205)

“This is our power. We are entitled. So use it.” (p. 206)