Now Comes The Hard Part

I don’t have answers, but I do have observations about what makes a good leader–based on 25 years of reporting on the topic. I believe that there are five key elements of successful leadership, and they are as applicable to the inhabitant of the most powerful corner office in the free world as they are to a 10-person startup. As a member of the hated mainstream media, I don’t expect President Trump to listen to me. But—as we learned yesterday—anything is possible; It’s worth a try. So here goes, Letterman-style, my top five list.

5. Humility

Many leaders are afflicted by what I call CEO disease. It seems to be endemic; not all executives succumb to it, but a lot more exhibit the symptoms than you might think. And it happens to many people who have made it to the top by being good, fair, and humble leaders.

CEO disease happens because people stop telling you the truth when you become the boss. Even if you are the nicest, most accessible person in the world, people who work under you often hesitate to tell you what’s really going on because it makes them look bad and endangers their job. So instead they tell you what you want to hear. Things like “You won the debate.” Whether you did or you didn’t.

As a result, leaders without humility—who don’t understand the implications of power—suffer significant consequences. They don’t have the information they need, and they choose to believe it’s because what they are doing is working just fine, rather than because their status as the boss prevents their underlings from telling them what’s really happening.

Trump’s identity is based on the absence of humility. On America: “I alone can fix it.” On women: “There’s nobody that has more respect for women than I do.” On walls: “I will build a great wall . . . and nobody builds walls better than me, believe me.” But sometimes people grow into the job. He did use the word “we” last night. Let’s hope.

4. Firm Decision-Making Backed by Evidence

There are different styles of decision-making out there: Some leaders want to hear from all sides before choosing one. Others prefer to forge ahead and act like they don’t need anyone’s help.

But the method, I’ve found, is not as important as the decision itself. Effective leaders make decisions relatively quickly. They weigh the evidence—and there needs to be evidence—then move decisively and don’t look back. They don’t overtly hem and haw, even if they are secretly terrified that they’ve made the wrong choice. They listen, move, and if they find they’ve made a mistake, they go back and start over. It’s better to make a relatively quick choice, I’ve found, than to linger so long that people lose confidence in your abilities.

Trump does appear to be a very fast decision-maker—just look at how many campaign managers he has cycled through—but his instinct to react rather than act is a true problem. So is the impulsiveness. This will have to change.

3. Don’t Fear the Future

The older we get, the more fearful we become. This is not true of everyone, but it’s certainly true of a lot of us. And if you are a leader, one who has made your way to the top because you understand “how things work around here,” you are more incentivized than most to stick your head in the sand and try to ignore the massive changes that are coming your way.

Leaders who do this might survive until the end of their contract, but they’re not going to motivate their constituents—or inspire employees to come up with, say, a new iteration of government. A good leader understands the fear and confusion that change brings, but doesn’t hide from it.

Trump is trying to take a pickaxe to the establishment, so I think it’s fair to say he doesn’t fear the future. On the other hand, when he talks about making America great again, he is talking about a return to the past. Which way will it go?

2. Manage Down as Much as You Manage Up

I see this problem everywhere—we all do. To get ahead, many people conclude that they need to kiss their boss’s butt and that’s the only relationship that matters. As they move up the ranks, they treat the people below them like vanquished enemies who no longer matter. And it seems to make sense—they won, right?

But every lowly assistant or middle manager has a looooonnng memory. When people have been humiliated or slighted, they never, ever forget it. And more than that, leaders can’t achieve their goals without the support of their troops. This is relevant in the military, in business, and in government. This does not mean that there aren’t hard choices that have to be made—that nonperformers shouldn’t be let go or that budget cuts aren’t a reality. It means that a leader needs to make sure he or she brings people along as those decisions are made, that they are treated with respect, and that even if they are below him or her on the totem pole that they still can have a very big influence in implementing—or ruining—a planned strategy.

Trump has a group of very loyal cadres–and some not-so-loyal new colleagues, like Paul Ryan. He cannot succeed in this job if he does not manage down (since managing up is kind of off the table). Can he do this? I think managing down may be one of his greatest challenges. But with little experience with the kind of giant bureaucracy he most now run, he cannot succeed without motivating his team.

1. And Finally, the No. 1 Leadership Trait: Authenticity

What, exactly, is authenticity from a leadership standpoint? In some ways, it’s a lot like the old saw by the Supreme Court Justice about obscenity: “I know it when I see it.” You also know it when you don’t see it—which explained much of the frustration and dissatisfaction over this election.

Authenticity doesn’t simply mean being honest, although honesty does play a role. It means being real, in good times and in bad. It means being true to your own style—which doesn’t mean pretending to be soft and fuzzy if you aren’t. You may not want to work at an investment bank, but people who do want to work there are prepared to work 18 hours a day. That culture—whether you like it or not—is, in its own way, authentic. It also means owning problems and bad decisions, taking responsibility, and making them right.

There’s no doubt that many supporters are attracted by what they view as Trump’s authenticity and his freedom from political correctness. But outrageousness is not authenticity. Once you get past a willingness to say almost anything—including things directly at odds with his previous statements and with reality—what do you have? The good news is that the slate is clean. Trump has a mandate–which could give him the space to be authentic. If he can do that, he has a chance to lead.