5 Lessons on Leadership From Barack Obama’s a Promised Land

“If I wanted to be president, I told myself, I needed to act like one.”

Jake Wilder
Jan 19 · 10 min read

“Oh, let’s not be petty, seeking sincerity in memoirs doesn’t make much sense,” wrote Polish poet and Nobel laureate Wislawa Szymborska, adding, “It’s worth asking what version of his self and world the author’s chosen — since there’s always room for choice.” And as anyone who’s had the misfortune of reading Sarah Palin’s Going Rogue (who knew you could fit that much BS in one book?) or Lance Armstrong’s It’s Not About the Bike (why rely on hard work when there are steroids?) knows, this skepticism is often warranted.

So it was with some reservation that I started reading Barack Obama’s memoir, A Promised Land. Maybe I’m biased by the YouTube-comment-forum-come-to-life that is today’s politics. Or maybe Obama’s leadership style shines especially well given the incredibly low bar set by the subsequent administration. Whatever the reason, it reminded me of just how fortunate we were to have him as a leader. And how absolutely deserving he was of that title.

He inherited a financial mess, two foreign wars, and an economy on the verge of collapse. He dealt with natural disasters, a pandemic, foreign uprisings, and one of the worst environmental accidents our nation has ever seen in the Deepwater Horizon spill. And through it all, he succeeded in moving the country forward on healthcare, immigration reform, foreign policy, and civil rights issues.

A Promised Land isn’t exactly a quick read, but it more than delivers as a deep dive into Obama’s journey to the White House and the challenges of his first term. Above all, at least for me, it showcased some of the key leadership principles that led to his success. While the book represents a treasure trove of advice for leaders of all experience levels, below are a few of my favorite.

“Looking back, I realize I was doing what most of us tend to do when we’re uncertain or floundering: We reach for what feels familiar, what we think we’re good at.” — Barack Obama

Obama knew economic policy. He could quickly process information and recognize the viability of certain strategies. It’s a great quality in a leader, particularly amidst the financial crisis in 2008.

This strength was invaluable for the economic recovery. Unfortunately, the rest of us lacked this knowledge. For the majority of Americans, the economy was, and continues to be, a black box mystery.

People just knew that it was broke. And they wanted it fixed. Right away.

Obama responded with economics discussions. He offered technical details and 10-point plans. All of which were very accurate. And all of which went right over most of our heads.

This failure to connect with people led to a lot of uncertainty. In a time where people needed reassurance, they couldn’t see a path through their current struggles. People were uncertain of whether his policies would lead the country through the recession. That uncertainty translated into Republican victories in the 2010 congressional elections as voters tried to hedge their bets.

He came out of this with a strong lesson. He recognized that the country’s success in coming out of the recession depended less on getting every economic policy correct to the last detail and more about inspiring confidence in people. All of which hinges on giving people a story they can use to understand their situation today and the path to a better one tomorrow.

In times of crisis, we all default to our strengths. They provide reassurance and help us build confidence in difficult situations. But these strengths can also be our blind spots. We ignore that risk at our peril.

“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.” — Barack Obama

Most leadership decisions are a matter of probabilities. You’re trying to decide which approach is more likely to succeed, or conversely, least likely to blow up in your face.

In these situations where there’s no right answer, just less wrong ones, digging for the perfect solution only leads to paralysis and inaction. Yet relying on your gut defers decisions to your biases, or worse, emphasizes short-term comfort over long-term investment.

The alternative is to establish a robust decision-making process, or as Ray Dalio describes in Principles, “I have found that triangulating with highly believable people who are willing to have thoughtful disagreements has never failed to enhance my learning and sharpen the quality of my decision making.”

Whether it was deciding to bail out the bank and auto industry, or weighing the risks of military action in Libya, Obama repeatedly surrounded himself with experts, developed sound alternatives based on facts and logic, and then considered their input against his own principles. By looking at each issue from multiple angles, refusing to discard potential solutions without a logical debate, and soliciting input from everyone in the room regardless of rank, he could make the best decisions given the limited information available. As Obama described it,

“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.”

Good leaders make good decisions. But you don’t need to do this on your own. Each problem offers the opportunity to build your own team of experts, reinforce ownership across your team, and further demonstrate your commitment to logic and your principles.

“I was tempted to call that man and explain that I was never more clear-eyed than on the flights back from Walter Reed and Bethesda. Clear about the true costs of war, and who bore those costs. Clear about war’s folly, the sorry tales we humans collectively store in our heads and pass on from generation to generation — abstractions that fan hate and justify cruelty and force even the righteous among us to participate in carnage.” — Barack Obama

The above quote was in response to a criticism of Obama’s visits to military hospitals. A former national security advisor wrote that a commander in chief shouldn’t perform these visits, as it would cloud his ability to make clear-eyed, strategic decisions.

His response is perfect.

There is always a cost to a leader’s decisions. Granted, most of our decisions don’t risk the lives of thousands of people. But that doesn’t mean there won’t be some impact to someone. When leaders distance themselves from the people who bear these costs, they quickly desensitize themselves to the impact of their decisions.

We see this all the time. We see pharmaceutical companies ruthlessly raise costs and make people choose between food and medication because it looks good on a balance sheet. We see automakers delay recalls, endangering their customer’s lives, because the math tells them it’s a more profitable decision. And we’ve seen administrations lock children in cages because it appeals to their base and the propaganda they’ve spewed for so long.

These decisions may make sense on paper. But no one associates them with strong leadership.

It’s actually the sign of an autocrat that locks themselves away from these impacts. They shut out the populace, surround themselves with sycophants, and make decisions based on their own personal interest as opposed to those they represent.

Good leaders don’t insulate themselves from the cost of their decisions. The moment they stop taking this responsibility, they stop making responsible decisions.

“I realized that for all the power inherent in the seat I now occupied, there would always be a chasm between what I knew should be done to achieve a better world and what in a day, week, or year I found myself actually able to accomplish.” — Barack Obama

You’re the President of the United States. You’re one of the most powerful people in the world. And you’re handcuffed from implementing the improvements that you want based on the need to convince 60% of Congress.

Ignoring the ridiculousness of the filibuster process — imagine doing something like that at your own workplace — it’s good that major legislation needs some bipartisan support. It forces our representatives to work together and develop solutions for the entire population, not just their own constituency.

But this also brings trade-offs and sacrifices. It forces compromise on the edge cases. And inevitably results in a solution that doesn’t fully align to the original vision.

This happened very publicly in trying to pass the Affordable Care Act. In order to get enough support through the Senate, Democrats needed to make concessions and trade-offs within the bill. The result was a less widespread healthcare bill than the Special Interest Groups sought. People soon began to see the ACA as a disappointment that fell short and not the major success and step forward that it was.

In these situations, it’s easy to fall into the trap of doing nothing, simply because you can’t do everything. Amidst criticism from both sides, it’s easy to set incredibly high standards and refuse to compromise. The downside, of course, is that nothing ever gets done.

Of the programs we know today, very few started as they are. This is true both in government and in our own workplaces. Every program begins as a first revision and then grows gradually over time as people gather more experience with it.

But this only happens if someone’s willing to take the first step. It only happens if someone’s willing to put out an imperfect first version. In the wise words of Edward Everett Hale,

“I am only one, but still I am one. I cannot do everything, but still I can do something; and because I cannot do everything, I will not refuse to do something that I can do.”

“So what are we saying here?” I asked. “That despite having the biggest Democratic majorities in decades, despite the promises we made during the campaign, we shouldn’t try to get healthcare done?” Rahm looked to Axe for help. “We all think we should try,” Axe said. “You just need to know that if we lose, your presidency will be badly weakened. And nobody understands that better than McConnell and Boehner.” I stood up, signaling that the meeting was over. “We better not lose, then,” I said.

One of the defining legacies of Obama’s leadership, more than any of the policies and programs that he put into place, is that hope will always be a more powerful motivator than fear. Fear leads to destruction and a return to the past. Hope inspires people to take responsibility for creating a better future.

As leaders, we build this hope through bold goals. We inspire people by taking on major challenges. But mostly, we build this hope by standing up for our values, regardless of the potential cost.

In the Affordable Care Act, Obama took on a long overdue challenge for this country. There were too many parents struggling to cover the cost of their children’s medical care. Too many people reserved healthcare for serious emergencies because they couldn’t afford preventative coverage. And too many people saw a potential cancer diagnosis as a guaranteed bankruptcy.

I don’t remember much of the economic policies that pulled us out of the recession. And the foreign policy wins wouldn’t come until later in his first term. But I do remember when the Affordable Care Act passed and the momentous achievement that represented. By sticking by his values, reinforcing the commitment with his team, and refusing to be timid in the face of adversity, he significantly improved the lives for millions of Americans.

This commitment also helped encourage others to demonstrate similar behaviors. When Mike Mullen, the chairman of the Joint Chiefs of Staff, was asked for his position on Obama’s plan to repeal the military’s Don’t Ask, Don’t Tell policy, he became the first sitting senior U.S. military leader to publicly state that LGBTQ persons should openly serve, stating:

“Mr. Chairman, speaking for myself and myself only, it is my personal belief that allowing gays and lesbians to serve openly would be the right thing to do. No matter how I look at this issue, I cannot escape being troubled by the fact that we have in place a policy which forces young men and women to lie about who they are in order to defend their fellow citizens. For me personally, it comes down to integrity, theirs as individuals and ours as an institution.”

“I pledge to be a president who seeks not to divide, but to unify. Who doesn’t see red states and blue states, only sees the United States.” — Joe Biden

While Biden’s methods differ from Obama’s in many ways, he also embraces many of the same leadership principles. His commitment to science and logic can be seen through his cabinet selections. His willingness to listen and consider all sides of an issue is evidenced by his bipartisan relationships. And his straightforward, principled manner shows that he’s driven by a similar set of core values that led Obama’s presidency.

After the division and anger of the last four years, bringing the country together won’t be an easy task. But I remain hopeful that Biden and Harris are up for that challenge. And I strongly believe that they’ll continue to build on Obama’s leadership legacy.

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