A Promised Land

Perspectives on Leadership

Communicating effectively is not just about the right facts

“Then again, a president wasn’t a lawyer or an accountant or a pilot, hired to carry out some narrow, specialized task. Mobilizing public opinion, shaping working coalitions—that was the job. Whether I liked it or not, people were moved by emotion, not facts. To elicit the best rather than the worst of those emotions, to buttress those better angels of our nature with reason and sound policy, to perform while still speaking the truth—that was the bar I needed to clear.” (pp. 88-9)

As the top leader, you only have direct contact with a small part of the organization

“A new administration brings less turnover than most people imagine: Of the more than three million people, civilian and military, employed by the federal government, only a few thousand are so-called political appointees, serving at the pleasure of the president. Of those, he or she has regular, meaningful contact with fewer than a hundred senior officials and personal aides. As president, I would be able to articulate a vision and set a direction for the country; promote a healthy organizational culture and establish clear lines of responsibility and measures of accountability. I would be the one who made the final decisions on issues that rose to my attention and who explained those decisions to the country at large. But to do all this, I would be dependent on the handful of people serving as my eyes, ears, hands, and feet—those who would become my managers, executors, facilitators, analysts, organizers, team leaders, amplifiers, conciliators, problem solvers, flak catchers, honest brokers, sounding boards, constructive critics, and loyal soldiers.” (p. 208)

Relying on a good decision-making process

“My emphasis on process was born of necessity. What I was quickly discovering about the presidency was that no problem that landed on my desk, foreign or domestic, had a clean, 100 percent solution. If it had, someone else down the chain of command would have solved it already. Instead, I was constantly dealing with probabilities: a 70 percent chance, say, that a decision to do nothing would end in disaster; a 55 percent chance that this approach versus that one might solve the problem (with a 0 percent chance that it would work out exactly as intended); a 30 percent chance that whatever we chose wouldn’t work at all, along with a 15 percent chance that it would make the problem worse.

“In such circumstances, chasing after the perfect solution led to paralysis. On the other hand, going with your gut too often meant letting preconceived notions or the path of least political resistance guide a decision—with cherry-picked facts used to justify it. But with a sound process—one in which I was able to empty out my ego and really listen, following the facts and logic as best I could and considering them alongside my goals and my principles—I realized I could make tough decisions and still sleep easy at night, knowing at a minimum that no one in my position, given the same information, could have made the decision any better.” (pp. 293-4)

Sometimes you just need to accept a bad situation

“Then I told myself that it was still the weekend and I needed a martini. That was another lesson the presidency was teaching me: Sometimes it didn’t matter how good your process was. Sometimes you were just screwed, and the best you could do was have a stiff drink—and light up a cigarette.” (p. 295)

Surprises are inevitable

“EVERY JOB HAS its share of surprises. A key piece of equipment breaks down. A traffic accident forces a change in delivery routes. A client calls to say you’ve won the contract—but they need the order filled three months earlier than planned. If it’s the kind of thing that’s happened before, the place where you work may have systems and procedures to handle the situation. But even the best organizations can’t anticipate everything, in which case you learn to improvise to meet your objectives—or at least to cut your losses. The presidency was no different. Except that the surprises came daily, often in waves.” (p. 385)

Leadership require patience

“THE PRESIDENCY CHANGES your time horizons. Rarely do your efforts bear fruit right away; the scale of most problems coming across your desk is too big for that, the factors at play too varied. You learn to measure progress in smaller steps—each of which may take months to accomplish, none of which merit much public notice—and to reconcile yourself to the knowledge that your ultimate goal, if ever achieved, may take a year or two or even a full term to realize.” (p. 483)

Playing it safe leads to mediocrity

“I reminded myself that it was part and parcel of the presidency for nothing to ever work exactly as planned. Even successful initiatives—well executed and with the purest of intentions—usually harbored some hidden flaw or unanticipated consequence. Getting things done meant subjecting yourself to criticism, and the alternative—playing it safe, avoiding controversy, following the polls—was not only a recipe for mediocrity but a betrayal of the hopes of those citizens who’d put you in office.” (p. 493)

Managing by walking around

“Keeping up morale, on the other hand, wasn’t something I could delegate. I tried to be generous in my praise, measured in my criticism. In meetings, I made a point of eliciting everyone’s views, including those of more junior staffers. Small stuff mattered—making sure it was me who brought out the cake for somebody’s birthday, for example, or taking the time to call someone’s parents for an anniversary. Sometimes, when I had a few unscheduled minutes, I’d just wander through the West Wing’s narrow halls, poking my head into offices to ask people about their families, what they were working on, and whether there was anything they thought we could be doing better.” (pp. 534-5)

Wanting to be an inclusive leader does not mean that one doesn’t have blind spots

“...But as I listened to these accomplished women talk for well over two hours, it became clear the degree to which patterns of behavior that were second nature for many of the senior men on the team—shouting or cursing during a policy debate; dominating a conversation by constantly interrupting other people (especially women) in mid-sentence; restating a point that somebody else (often a female staffer) had made half an hour earlier as if it were your own—had left them feeling diminished, ignored, and increasingly reluctant to voice their opinions. And while many of the women expressed appreciation for the degree to which I actively solicited their views during meetings, and said they didn’t doubt my respect for their work, their stories forced me to look in the mirror and ask myself how much my own inclination toward machismo—my tolerance for a certain towel-snapping atmosphere in meetings, the enjoyment I took in a good verbal jousting—may have contributed to their discomfort.” (pp. 535-7)

On taking risks when the loss of human life is on the bad side of the risk

“When someone asks me to describe what it feels like to be the president of the United States, I often think about that stretch of time spent sitting helplessly at the state dinner in Chile, contemplating the knife’s edge between perceived success and potential catastrophe—in this case, the drift of a soldier’s parachute over a faraway desert in the middle of the night. It wasn’t simply that each decision I made was essentially a high-stakes wager; it was the fact that unlike in poker, where a player expects and can afford to lose a few big hands even on the way to a winning night, a single mishap could cost a life, and overwhelm—both in the political press and in my own heart—whatever broader objective I might have achieved.” (pp. 666-7)

Personal Reflections

On getting serious about self-improvement

“This, too, can be found in my journal entries from that time, a pretty accurate chronicle of all my shortcomings. My preference for navel-gazing over action. A certain reserve, even shyness, traceable perhaps to my Hawaiian and Indonesian upbringing, but also the result of a deep self-consciousness. A sensitivity to rejection or looking stupid. Maybe even a fundamental laziness. 

“I took it upon myself to purge such softness with a regimen of self-improvement that I’ve never entirely shed. ...I made lists. I started working out, going for runs around the Central Park Reservoir or along the East River and eating cans of tuna fish and hard-boiled eggs for fuel. I stripped myself of excess belongings—who needs more than five shirts?” (p. 13)

On using privilege to serve rather than building more privilege

“‘But I need to tell you, Barack,’ [Michelle] said, ‘I think what you want to do is really hard. I mean, I wish I had your optimism. Sometimes I do. But people can be so selfish and just plain ignorant. I think a lot of people don’t want to be bothered. And I think politics seems like it’s full of people willing to do anything for power, who just think about themselves. Especially in Chicago. I’m not sure you’ll ever change that.’ 

“‘I can try, can’t I?’ I said with a smile. ‘What’s the point of having a fancy law degree if you can’t take some risks? If it doesn’t work, it doesn’t work. I’ll be okay. We’ll be okay.’ 

She took my face in her hands. ‘Have you ever noticed that if there’s a hard way and an easy way, you choose the hard way every time? Why do you think that is?’” (p. 22)

On realizing that his motivations were not pure

“I was almost forty, broke, coming off a humiliating defeat and with my marriage strained. I felt for perhaps the first time in my life that I had taken a wrong turn; that whatever reservoirs of energy and optimism I thought I had, whatever potential I’d always banked on, had been used up on a fool’s errand. Worse, I recognized that in running for Congress I’d been driven not by some selfless dream of changing the world, but rather by the need to justify the choices I had already made, or to satisfy my ego, or to quell my envy of those who had achieved what I had not.” (p. 38)

On “destiny”

“The truth is, I’ve never been a big believer in destiny. I worry that it encourages resignation in the down-and-out and complacency among the powerful. I suspect that God’s plan, whatever it is, works on a scale too large to admit our mortal tribulations; that in a single lifetime, accidents and happenstance determine more than we care to admit; and that the best we can do is to try to align ourselves with what we feel is right and construct some meaning out of our confusion, and with grace and nerve play at each moment the hand that we’re dealt.” (p. 65)