The phone rang at the appointed hour. My client, a software company CEO, was calling for his regular session. I picked up the phone:

“Hello”

“Why the hell does my board act like that?”

“Good morning, James,” I answered and we both laughed.

We talked through the upcoming financing. Some of investors—folks who came into the company only in their last round—were already jockeying around terms and prices of the upcoming round. Some of the other directors—investors who’d been with the company since the beginning—were also beginning to draw a hard line around terms that they would find acceptable.

In a sense, while they were all directors, as investors they were beginning to play a game of chicken with the company’s financing—each holding fast to a position deemed best for the shareholders they represent and yet, as the negotiations would tick on, the company’s ability to actually raise the needed funds could be jeopardized.

After the session, I asked him he if I could quote him.

“Sure,” he wrote, “just let me know if I ever end up there with an actual video recording of me calling [the board member] a ‘fuckhead’ – it’s not that I’d be bothered by that, it’s just that I’d want to make sure I sent the link to all my friends.”

A year ago I was sitting in office of the CEO of a company on whose board I served. The recently elected chair and the CEO were screaming at each other and, as usual, I found myself trying to meditate.

“What you don’t understand,” said the chair rising from his chair and trying to tower over the seated CEO, “is that you’re here,” and he held out his right hand, palm down, “and the board is here,” and he moved his left hand on top of the right, again palm down, “and I’m here,” and he placed his right hand over the left.

Capo dei capi—boss of bosses.

My client’s question was spot on: Why does this happen? What is it that makes the relationship between board members, investors, and management so tricky? And, even when you remove the notion of director as investor (or investor representative) you can still end up with troubled relations.

The board/management relationship is tricky, complex, and nuanced. There are few structures within traditional businesses that are quite like it. Most businesses, indeed most organizations, are built on some variation of a command and control structure. Because of their inherent hierarchical nature, it’s often clear who’s in charge, who makes the decisions, and who’s ultimately responsible.

Even in enlightened business, as people like Warren Bennis have pointed out, where the power and decision making reflects not the pyramid of classic command and control but the inverted pyramid of the ways in which information, and therefore, accountability should flow, there’s relative clarity.

But when it comes to boards of directors, confusion is often the norm and, as a result, there’s often frustration and anger. For example, does the CEO work for the board of directors or the company? Does the Board “work” for the company? Who holds individual board members accountable for the actions? And what is the relationship between board and staff members?

And underlying all of this is the responsibility to represent the shareholders.

I’ve served on dozens of boards of directors; this includes public and private companies, for profit businesses and not-for-profit organizations and I think the core troubles stem from a misunderstanding of the key elements of the roles.

Directors aren’t quite like any other management position in an organization. They have power but often times lack the information to wield that power as well as managers. They have perspective—often times significantly more experience than senior management but, by the nature of their responsibility, they are disconnected from the day-to-day operations.

Directors need to remember they’ve a delicate balancing act of influencing without dictating, and engaging and sharing their experience and perspective by virtue of their gravitas as much as a result of their power.

Management, too, needs to remember that the task of being a director or a trustee is unlike any other job one has ever had. There’s an explicit accountability that goes along with the job and that fact, combined with the implicit lack of information, can cause most folks to feel terribly anxious and to act in awful ways.

Everyone on both sides of that divide need to take a step back, see things from the other view, and work towards making the board as functional as possible.

As my friends and colleagues are tired of hearing me say, I’ve never seen a board guarantee an organization’s success but I have seen it guarantee its failure.

I’ve nothing nothing poetic or particularly artful to say today. Just wanted to acknowledge my client Ben Saunders. I first started working with Ben two years ago when he’d come back from a failed attempt to set a new speed record for a solo, unsupported trek to the North Pole. Two days ago, he landed at the edge of the Arctic Ocean and he’s trying again. His attempt–to make it to the Pole in 30 days or less–would shatter the previous record of 36 days 22 hours which I believe was set more than 100 years ago by a team traveling by dogsled. So far, he’s traveled 14 nautical miles with just over 460 miles to go. And with the changes in the global climate, and the implicit changes to the constancy of the sea ice, this may be the last time someone could do this.

Alone, on the ice, for 30 days. Sheesh. I thought of Ben, again, as I dragged myself to the gym this morning at 5:30. He’ll be blogging via satellite phone and you can follow him @polarben. Thanks Ben, for changing my life.

I know this guy…when he was about ten…his father lost his job. The father came home one night, just around Christmas, and announced that the company he’d worked for 30 years or so was closing down and he’d be out of a job. This guy always said it was one of the few times he’d ever seen his father cry.

Watching his father struggle over the next few years, bounce from union-provided job to union-provided job, made him feel like he could never ever depend on anyone else to employ him. He knew, he says, from the fact that his father was never the same that he’d never let that happen to him.

That view—that he’d always be responsible for his own employment-dogged him for years.

Then there was the job he had as a teenager. He worked for five years in a locker-repair company. (I know, I know. You never think about it but somebody has to fix all those lockers in school.) Anyway, it was a great summer job. He’d work from early in the morning until mid-afternoon and still have time to go out with his friends at night.

Even better, he worked for this older man who, it seemed, was completely unlike his father—especially when his father was unemployed and sitting around the house. The older man could fix anything and taught the guy how to use his hands. And in doing so, the guy always says, he learned that—if nothing else, he knew how to swing a hammer. He’d always be able to work.

College came and with it a series of survival jobs. Each took him further and further away from his childhood and deeper into his manhood. One year he won a scholarship and a summer job from a publishing company and he turned that summer job into a permanent part-time position until he finished up school when he was hired fulltime.

Later, after a few years at the publishing company, the guy’s father advised him against taking a job that would require him to move. It was promotion out of his current job—a place he’d been working for a few years—and his father cautioned that the “higher up the pole the monkey climbs, the more his ass shows.” He followed his father’s advice but he stewed on it, it gnawed at him.

Later, when he was about eight or nine years into what had become a career at that company, he remembered the advice, and more important, remembered the regret. And so when an opportunity to be promoted, to take a risk, to take a job off the successful track he was on, he decided to go for it.

It helped, in a way, that when he went to his then boss to announce he was taking the internal, lateral promotion within the company, the boss went ape-shit; told him he was an idiot, that he’d never amount to anything, and he’d be stuck in the dead-end corporate job forever. And when the guy just stared at his boss and said nothing, the boss said:

“I know what you’re thinking…you’re thinking you’re going to take this job and prove me wrong.”

The guy stood up, calmly said, “That’s exactly right,” and walked out into the rest of his life.

That guy was me.

After I left that job—as Editor of InformationWeek—I ended up, after a stop, working with a group that started TechWeb, one of the earliest entities on the Web to accept advertising. And after that, I left the company and started a ten-year career as a venture capitalist.

There are dozens of events that shape our careers, our lives. There are the little conversations at the end of the day, over a cup of coffee, that reframe everything.  There are the daily mantras we grow up with that shape our values and our sense of the right thing to do in life. And there are the large events, like when my father lost his job, that cause us to take on a new point of view, a monster if you will. In my case, that view has sometimes cost me but more often than not caused me to push ahead, to try different things, to explore, to take risks. In a way, I wouldn’t be the man I am today had I not watched my father struggle through his years of un- and underemployment and had it not been capped by that fearful advice he’d given. For good or for ill, and in full-blown rebellion against my father, I’ve never been afraid to let more of my ass show.

Today, as a coach, I consider myself one of the luckiest people alive. I get to hear peoples’ stories. I get to help people merely by listening deeply and holding onto their stories while they do their work. And among all the things I find so remarkable are the ways in which our lives are shaped by these conversations from our pasts.

In a book I often use in my work-especially with men–psychologist Samuel Osherson explains the impact of these real and imagined conversations on our current lives:

It’s not true…that your father comes to you only once and forever; you meet him again and again in different guises through your whole life. We relive with our mentors our ambivalence over our fathers’ messages as to what it means to be a man. Many men learn from their fathers that to be in the work world means to suffer, indeed that manhood itself is a kind of dreadful obligation. Finding Our Fathers: How Man’s Life is Shaped by His Relationship with His Father

It helps to understand the stories of our lives. It helps to see clearly the ways in which a word or two changed everything. Seeing the patterns that ripple out from those tossed stones of events, conversations, and interactions allows us—if nothing else—to see even more clearly how we became who we are. As I often say with my clients, a good first step to figuring out where you want to go is remembering how you got here.

It happens all the time with my clients. As we talk, as we unfold, a sort of psychic bond gets formed. A paper I read recently talked about how much greater is the role of the unconscious than ever imagined before. And equally compelling, said the author, the unconscious leaps out of the mind of one and connects with the other; the boss sneezes and everyone catches a cold.

My client was talking about his overwhelming anxiety. It’d gotten so bad that he’d felt paralyzed—unable even to get to the office. Later, after working through those issues, I asked, “And how are your employees feeling?”

“Anxious, worried about running out of cash,” and the light bulb turned on, “…just like me.”

Yup, I thought, the CEO sneezes, the unconscious leaps from one to the other, feelings are contagious.

I remember when I was a young VC; I think even my hair was mostly black at the time. I was working almost daily for one of my portfolio companies (“Gone native,” as an elder VC put it to me later—but more on that in another post). I stood before the small, nascent team and present the product plan my team had developed. And, as soon as I stood up, the CEO, who’d been standing at the back of the room, turned and walked out.

I furiously called him on it. “I left,” he said, “because I knew I could trust you.” But your action sent the opposite message, I told him. You sent the message that what I was saying was unimportant. Achoo.

So what’s our responsibility as leaders, co-workers, spouses, companions, parents, children, and friends when our unconscious decides to telegraph a message we didn’t intend or spread a feeling we’d rather keep inside?

The question itself is dangerous because, if approached from the wrong angle it could induce a sense of responsibility for others’ feelings that-quite frankly– would emerge as a Monster in Your Head. Even the CEO isn’t responsible for how an employee feels about their job. But there is an undeniable, implicit shared mutality of experience (as one fourth grader in this amazing documentary about teaching feeling and empathy in a class room put it: when one of us is unhappy, we’re all unhappy).

The fact that we, as co-workers, co-create the emotional as well as the financial experience of the company makes this report from CNN remarkable. A client sent me the link and, after I got over the macabre satisfaction of having the purpose of my work affirmed, I was struck by the notion that the dominant emotional aliment felt by CEOs was loneliness.

Upon the king! let us our lives, our souls,
Our debts, our careful wives,
Our children and our sins lay on the king!
We must bear all. O hard condition,
Twin-born with greatness, subject to the breath
Of every fool, whose sense no more can feel
But his own wringing! What infinite heart’s-ease
Must kings neglect, that private men enjoy!

Henry V—William Shakespeare

In other words, it sucks to be the king (or the CEO, or the boss, or the captain or whoever it is in whose hands we collectively place our feelings). And if this is the dominant feeling, and if we unconsciously infect others with our feelings, then is it any wonder that businesses are such lonely places?

Michael Carroll, after he wrote Awake at Work but before he published The Mindful Leader, published an article in which he says that “the best leadership first occurs from the inside out—offering to others a part of ourselves that inspires them.” Although he doesn’t make this explicit connection, he’s in effect suggesting making the unconscious sharing–the infecting, if you will–a conscious act:

“There is a fundamental human gesture that must take place first, before any leader can guide, direct, or point the way. Leaders must first open. They must step beyond the boundaries of what is familiar and routine and directly touch the people and environment they want to inspire. Leading others requires that we first open ourselves to the world around us.”

If he’s right about the need for inside out leadership, Carroll’s not only come up with an intriguing manifesto for leadership but an antidote to what ails the CEOs in all of us. The best way to overcome the inevitable loneliness of life at the top may be to connect and mindfully attend to the process that’s already underway—the unconscious sharing that undergirds every relationship.

There are two things worth knowing about me: I am a ruminator and I am a sucker for Oreos.

I thought of this earlier this week after hearing Paul’s story.

“I only got three hours sleep last night,” he said. “I couldn’t stop thinking about that damn email.”

“What were you thinking about as you lay there?” I asked.

“I kept composing my response. It was like I was replaying the whole scene over and over again, getting some sort of crazy pleasure out of torturing myself.”

My friend Jane does the same thing although she’ll take it to a whole new level. She’ll ruminate, replay the scene, re-write the script of what actually happened while she’s in the middle of a conversation with someone. It doesn’t show of course. The only thing that the other person sees is Jane drifting off (“running silent; running deep,” my witty friend Tom—an ex-submariner—calls it).

“Why do you leave at that moment?” I ask her.

“I don’t know—I think I’m trying to figure it out–somehow make what happened better or not at all.”

I know one CEO who drifted off, ran deep, in the midst of a board meeting, in the midst of intense questioning by a director. As the director pressed and pressed for answers, he says, he couldn’t stop thinking of the mistakes he’d made.

As Paul and I talked the other day, we struggled with the core questions: How do you break through the obsessive rumination, self-recrimination, re-writing of the script? How do stop yourself from disappearing from the present moment of your life? How do you fall asleep?

And then I thought of my relationship with Oreos.

Seven years ago I was  nearly 50 lbs. heavier than I am today. Frustrated, angry, disgusted with myself, I hauled my (fat) ass into a nutritionist’s office. Erica gave me a lot of tools (including a whole new approach to food) but the most important gift she gave me was the power of “Do Overs.”

One day I came in to see her, dejected and ready to give up. I whined: “I ate a fucking dozen Oreos last night, Erica…a fucking dozen.”

“Well the combination of sugar and salt is deadly for you. Some folks like sweets. Some like salts. You’re one of the lucky few,” she said with sweet sarcasm, “who craves both. An Oreo is the perfect drug for you.” And then she gave me the gift: “Tonight, it’s a Do Over. Start again.”

And suddenly I was 12 and back on West 7^th Street and Avenue T, playing stick ball with Paulie, Ugo, and Pino. And we were arguing about whether Paulie’s shot was a hit or a foul and to stop the fighting, Ugo yells “Do over!” and just like that, all is forgiven, all is forgotten. It’s not an out. It’s not a foul. It’s not a hit.  Do over.

Later—much later—I’m reading Zen Mind, Beginner’s Mind and I realize that coming back to the Beginner’s Mind is a Do Over…and if I allow myself, then I can have an infinite number of Do Overs. I can always return to what is, what is really happening, what is really present. Even more powerfully, if I do that, then I can let go of the email, let go of the missed quarter, let go of the Oreos.

Of course that’s hard. And harder still is letting it go while taking in the implicit lessons. Oreos with high salt and high sugar are a drug for me. The email pricked that bubble of self-confidence and revealed the deeply and long held fear of being found out as the less-than competent person that was projected.

Several years ago I taught an undergraduate class in business leadership at Queens College. From the beginning I had, what to the students seemed a revolutionary policy: You always got a chance to re-write your essay. If you didn’t like the grade you got the first time, you could incorporate my suggested changes (or not) and re-submit your essay at least once.

The lesson I tried to teach was that doling out Do Overs was a powerful incentive. It mitigated the fear of failing and, more often than not, brought out the best in the kids.

Many walked away with the notion that they, too, when they ran their own companies (and they all thought they would one day), would hand out Do Overs. Fewer of them, though, walked away with the deepest lesson of all: you’ve got the magic wand in your hand right now. Give yourself a Do Over. Let go of the shame, guilt, anger, fear from eating too many Oreos and try again today.