Part of what makes the lecture seem so important is the audience hearing it. West Point students are the kind of people who could have gone to Wall Street or started a company two years out of school but instead will soon find themselves face down in the dirt of Afghanistan on Christmas day, scared and cold, leading people they’ve just met, under circumstances that would overwhelm folks like me.

But mostly, I love the essay because the old professor gives the plebes such strange and good advice. In the plainest terms, the lecture captures everything I’ve been feeling about these charming hoop-jumping robots Redfin has been interviewing at top-flight schools this fall  – smarter, more polished people than I am who’ve never had a goofy moment of pure curiosity, who never blew stuff up for fun or were allowed to make terrible mistakes, who never screwed up their transcript or their resume just to see what it would feel like to stop pleasing everyone else.

Interviewing such poised job applicants, I kept thinking this fall of Wagner’s complaint about Mendelssohn, who was more precocious even than Mozart and more lyrical: that he never lost control of himself. Drawing on decades of grooming Ivy League students, Deresiewicz argues that this control is crucial to being successful in society, but not to being a leader. His students are always thinking of how to get to the next step, but always on someone else’s stairway:

So I began to wonder, as I taught at Yale, what leadership really consists of. My students, like you, were energetic, accomplished, smart, and often ferociously ambitious, but was that enough to make them leaders? Most of them, as much as I liked and even admired them, certainly didn’t seem to me like  leaders. Does being a leader, I wondered, just mean being accomplished, being successful? Does getting straight As make you a leader? I didn’t think so. Great heart surgeons or great novelists or great shortstops may be terrific at what they do, but that doesn’t mean they’re leaders. Leadership and aptitude, leadership and achievement, leadership and even ex­cellence have to be different things, otherwise the concept of leadership has no meaning. And it seemed to me that that had to be especially true of the kind of excellence I saw in the students around me.

The essay argues that what a leader really needs is solitude — the kind you feel when completely absorbed in a creative project, or on a long car ride through an empty place. For me that solitude has come most intensely running up a mountain, all alone in winter, with darkness coming and the snow falling as thick as the air itself, running until I’ve thought through what to do with my life or decided how I really feel about God, running so far that I’ve started to get scared about making it back alive. Deresiewicz worries this solitude is being drowned out by modern life:

“Your own reality—for yourself, not for others.” Thinking for yourself means finding yourself, finding your own reality. Here’s the other problem with Facebook and Twitter and even The New York Times. When you expose yourself to those things, especially in the constant way that people do now—older people as well as younger people—you are continuously bombarding yourself with a stream of other people’s thoughts. You are marinating yourself in the conventional wisdom. In other people’s reality: for others, not for yourself. You are creating a cacophony in which it is impossible to hear your own voice, whether it’s yourself you’re thinking about or anything else.

What I love most about the essay is that it talks about  how the solitude that a leader needs — that anyone needs — is not incompatible with friendship, especially the friendship of one person, someone you know well enough to welcome into your solitude:

Introspection means talking to yourself, and one of the best ways of talking to yourself is by talking to another person. One other person you can trust, one other person to whom you can unfold your soul. One other person you feel safe enough with to allow you to acknowledge things—to acknowledge things to yourself—that you otherwise can’t. Doubts you aren’t supposed to have, questions you aren’t supposed to ask. Feelings or opinions that would get you laughed at by the group or reprimanded by the authorities… Instead of having one or two true friends that we can sit and talk to for three hours at a time, we have 968 “friends” that we never actually talk to; instead we just bounce one-line messages off them a hundred times a day. This is not friendship, this is distraction.

I was lucky to grow up always having a friend like this: until we left one another for college my twin brother and I lived in our own country, unassailable and determined. The French describe a newly married couple as, “alone, just the two of them,” a phrase that perfectly describes the feeling we’ve had together.

Over time, I’ve been lucky enough to make new friends like that, but lately not so much. I don’t know if I’ve gotten too old, or too busy — I’ve often just felt that I’m no longer gooey, that my identity has sadly hardened to the point where it can hardly accommodate the shape of a new personality. But Deresiewicz’s beautiful lecture convinced me that there are, at least, a few more kindred spirits out there, for all of us.

Brian has worked with and for all sorts of leaders in his career which, in addition to his time at aQuantive, has included stints at General Mills, Capital Cities/ABC, Disney and Microsoft. His advice is based on the great bosses he’s worked for and the bad bosses, and from his own experience as a CEO. As he laid out seven best practices, we did our best to keep up with what he said. Below is not a transcript – no one at Redfin is a stenographer, and I don’t take much time to clean these notes up later — but some of the useful bits and pieces of what he said, in as close to his own voice as we could get:

Set clear objectives, hold people accountable and get out of the way: if I had to sum up my management philosophy, this would be it. You want objectives to be aggressive but achievable. Push decision-making down and out in the organization, essentially closer to the customer. At aQuantive, we tried to empower people in sales and support. That means you have to have the right incentives, the right objectives and parameters. But within that framework, the more you can push P&L responsibility out, the better. This will help you attract and retain the best people. Do you want to be the only leader in your company? No…

One of the fundamental responsibilities that a manager has is building a team. Who is on their team is their call. That’s the most important decision a manager makes. I interviewed candidates for managers who reported to me, but this was only to give input and of course to help in recruiting the candidate. I once met a candidate who one of my direct reports wanted to hire who didn’t really do it for me. He hired the candidate anyway, and about six months later he fired that person. We hurt ourselves over that six months, but the manager who hired him also hired five or six good people too. That not’s a terrible batting average. I used to tell my own board, “If you don’t like the team I’m hiring, then fire me.” I held that manager to the same standard.

Micromanagement does not scale. Founders can be micromanagers. Sometimes micromanagement comes from a vision, sometimes it comes from a manager just being insecure. Micromanagement results in the loss of talented executives. Do you want people working for you who just take direction? Or do you want people who are going to lead, who are going to push back? We all know of some visionary founder or “celebrity CEO” who may have a reputation for micromanagent and so we ask: what about him? Doesn’t he prove you wrong? My answer is “no.” First of all, if the company is truly successful, my bet is their micromanagement is seriously overrated. Or if not, they are an extreme exception — and they’ll be in deep trouble when that person leaves since the people below him or her have not been trained to lead themselves. To support the “exception” point, look at lists of the top companies: best-run companies, best-managed companies, best places to work. The vast majority of these companies – if not all of them – are not led by these “celebrity CEOs” with micromanagement tendencies. In fact, the best companies to work for are led by CEOs you couldn’t name.

The way to get job security isn’t to own every decision, but to hire smart people. The board may say, wow, this person is better than you are. That’s a risk I’m willing to take. I often tell people who work for me: “The more you tell me, the less I will bother you.” Tell me what’s going on in our one-on-ones and I’ll stay out of your hair.

Micromanagement is a virus: the time and energy wasted by people down in the organization modeling that behavior is huge. When I have to present to a micromanager, I’m expected to know everything just as he would, which is a waste of time. As CEO at aQuantive, I was once asked at a board meeting what I thought of an executive’s presentation, and I said you already heard what I think. That executive knew more about the topic than I did, and he represented my point of view. Maybe the Board wanted me to have some special insight, but my insight was hiring him.

It is far more important to be respected than liked: act with integrity, be honest and transparent, treat people with respect and dignity. Being direct and honest often can mean delivering difficult news, news that people don’t want to hear. Some people don’t get that. A senior HR person I worked with viewed his job as what might be called a union leader, to lobby for whatever the employees wanted. Yes, your job is to represent employee needs to management, but it’s also to represent management to the employees.

Some decisions employees won’t like. My standard was: “Could I be ok with a decision that showed up in the New York Times, could I defend it?” For example, a compensation decision: could I defend to this manager why I was paying his or her peer more than her based on their performance. Of course in a public company, the New York Times rule comes true, as many executives’ compensation is public.

That can create some interesting dynamics. At aQuantive we said we had no politics, and certainly we had very little politics. We could be direct and transparent, where people said what they felt in the meeting. In my view, for someone on my executive team, the worst thing you can do is not say anything in a meeting, then come in my office afterwards and tell me what you really thought. When people tried to do that, I’d say, “I don’t want to be a middle-man. Say what you think in the meeting.”

Give employees the right to be wrong: if we’re not making mistakes, we’re not taking enough risks. Just don’t make the same mistake twice. Make a mistake for the right reasons, for a client, for the business. Learn from your mistakes, and teach everyone. There are exceptions: mistakes of integrity are one-strike-and-you’re-out. Otherwise, mistakes can be good. One of my colleagues used to say: “The reason we’re better than other companies is because we’ve made more mistakes than they have.” Encourage a culture of admitting mistakes. No excuses, but explanations are fine. It’s great when a senior leader says in front of her boss that she made a mistake, it’s critical for others to see that, to see that it’s accepted, and not punished. It’s great to ask what might be considered “dumb” questions, and it’s great for other folks to see you ask dumb questions; you should model that behavior as an executive.

No jerks: no matter how smart someone is, if someone can’t get along with others, if somebody treats others badly, they’re out. Sometimes you worry that somebody is too smart to fire, too valuable to fire. That’s never true. The collateral damage that is being done to the morale and effectiveness of the people that “jerk” is interacting with is enormous, even if it is often hidden from his or her direct boss. When you do make the decision to fire someone who is a “jerk”, you often hear that the whole team will quit. That never happens either. Hire slowly, fire quickly. It’s right for the team, it’s right for the company, it’s right for the person leaving.

Have a bias for action: gather the data you reasonably can and make a decision. What people don’t realize is that sometimes doing nothing is a decision. You can get bogged down with consultants, meetings, PowerPoints. You want an organization where it’s always clear who is supposed to make a decision. This lets some people give input and others make the decision rather than having two people both posturing, because they’re vying to make a decision. And always align authority and responsibilty. You don’t want to be in a situation where you have no authority but you’re still accountable, where you can get blamed for something you didn’t do; or conversely, where someone who does make the decisions is not held accountable for them.

As CEO, I always felt the fewer decisions I was making, the better we were doing.

Live or die by your values: most companies have values but they often have too many. Who can remember 13 values? aQuantive only had four values, and everyone knew them. It was hard to pick just four; someone, for example, would say excellence has to be a value, I mean, don’t we want to be excellent? My job as CEO was to pick just four. What other decisions did I have to own? Well certainly picking the team was the most important. Acquisitions were a big part of our strategy. I had to make the final decision on compensation and budgets.

And that was it. What was interesting about Brian is that on the one hand he’s such an indelible figure – tall, with a deep voice uninflected by many doubts – and yet he stood in front of us for an hour trying to do the impossible, erasing himself bit by bit so you could see all the other great leaders at aQuantive more clearly. Many thanks to Brian for coming by, and to Madrona for hooking us up with him. We had a lot of people at Redfin buzzing about it, and already one meeting on Friday night giving someone authority over a problem he’d previously had to helplessly take the blame for — so it was definitely a big hit.

Any comments or questions for Brian, just post ‘em below and we’ll make sure he takes a peek.

(Photo credit: Jeff Louella on Flickr)

Redfin’s Matt Goyer read it first, to make sure it wouldn’t offend anyone. Matt’s an insightful soul, so I knew he would also appreciate the nuances of my argument.

When he was done, he looked up and said, “So you’re saying I should be a ***hole.”
“No,” I said, “I’m saying you should be a sensitive ***hole…” We stared at each other. “Or maybe not an ***hole at all.”

It’s a tough balance. As the CEO of InterContinental Hotels Group said of himself in a recent New York Times profile: “I’m very sensitive to how people are thinking and feeling at any given moment.”

But he also described himself as a super-action hero, boldly acting on his own in ways that surprised everyone. And this is what’s nearly impossible: to know how a decision will make everyone feel, then to make that decision anyway. It’s why many great technology entrepreneurs have mild forms of Asperger’s syndrome: it frees them to act, to decide, to drive people without much emotional friction.

If you don’t start that way, maybe that’s how you end up. Last week, I saw the “September Issue,” a documentary about Anna Wintour, the head of Vogue Magazine, and her efforts to publish its phone-book-sized September 2007 issue. It was moving to see so many flamboyant, talented people work so hard to make something irrevocable, definitive and perfect; many are undoubtedly now unemployed.

The entire movie consists of Anna walking into one room after another, picking one skirt or photo out of 50, and leaving the creators of the other 49 absolutely annihilated.  Time and again, she is asked how she feels. She mostly answers with the warmth of a bare steel table.

For some, it is necessary to be this way. The historian Edmund Morris described a day he spent with President Reagan, starting just outside the elevator with an unscripted photo opportunity alongside a police officer, blinded in the line of duty. This meeting and the ones that followed put Morris through the wringer; the sensitive writer was exhausted by lunch.

But Reagan, famous for momentarily failing to recognize his own son in a handshake line, deftly moved from one emotionally drenched encounter like this to another without apparently feeling a thing. Morris concluded that this detachment was the only way Reagan could make any decision affecting millions.

I don’t know if the choice is that stark for all of us. In the mostly dreadful Wim Wenders film, “Wings of Desire,” the angels can hear the thoughts of everyone in a train, on a street or in a cafe. The film is a near-unbearable cacophony of mortal thoughts that gradually becomes a comforting hum. When one angel forsakes his heavenly powers, he enters a cone of silence, unable to know what anyone is thinking but now able to act in the world. He can’t believe how lonely it is.

This loneliness is all well and good if you’re Ronald Reagan, or Anna Wintour, or an angel, who knows just what to do. But for the rest of us, the cacophony is essential to making a decision.

We engage people because we have to in order to figure out the best course of action. This is what makes deciding in the end so painful: that we’ve identified with a point of view completely that we then have to reject. It is hard to be emotional and then unemotional. It is hard to lose yourself in your company’s mission without occasionally forgetting the feelings of the  people on the mission with you.

But I have never given up on the idea that you can — and you have to — strike a balance between empathy and decision.

There are unlikely heroes — the man who first recommended Dick Cheney to be secretary of defense or the blogger who called us out for our TechCrunch post on surviving a recession — and one or two villains too.

Redfin stats expert Mose “The Underground Man” Andre will be pleased to see another Segway reference, reinforcing his comparisons between me and the Segway-riding illusionist on Arrested Development. Thanks to John Cook and Todd Bishop for agreeing to publish the essay.

Any guesses on where the title of this post came from?

Update:  AllThingsD re-posted the essay last night.

It’s odder still to hear Republicans accept that premise, arguing that McCain or Palin are up to the job. No one who has ever run a large technology business thinks that McCain or Obama, much less Palin or Biden, is qualified to run a large technology business.

At the very least, it requires an interest in technology, or business. Which is just another way of saying that setting government economic policies isn’t the same as getting a printer to ship on time. Only in countries like North Korea are we outraged if someone implies that the Dear Leader can’t beat Michael Jordan at basketball, or perform brain surgery.

Yet why are politicians so eager to be seen as CEOs? As former CEO Dick Cheney would tell you, the qualities that many people admire in a CEO – the single-minded pursuit of an objective, with a long-discarded regard for whether people like you or not — can create problems in political office. Undeterred, Sarah Palin now describes herself as the CEO of Alaska. And George Bush’s governing style has often admiringly been compared to that of a CEO.

The image these would-be CEOs seek to project is one we are now eager to admire. Whereas Americans once rooted for Teddy Roosevelt in his battles against tycoons, it seems like the public respects the imperial power and instinct for plunder of executives rather than politicians’ mealy-mouthed idealism and legislative give-and-take. The pied piper of the preceding generation was John Kennedy; today it is probably Steve Jobs.

But the charter of the President is so much larger and more humane than running a lemonade stand, even one of HP’s size. When Michael Dukakis said “it’s about competence” we all immediately recognized he was wrong: yes, someone like the CEO of HP has to be competent, but the presidency has a moral dimension that is, well, inspiring.

The best thing about Obama is that he chose not to be a CEO, instead devoting his time to helping poor people get a better life. The best thing about John McCain is that he served his country in a war. Sure, maybe if they’d spent their youth climbing the greasy pole at HP, they’d be ready to run HP. But I’m glad they didn’t.