When do you know? I mean, really know?

Slumped into my couch, pale from a lack of sleep, nose red from the cold he can’t shake, the CEO shook off my suggestion about this being the time to hire an assistant.

“I know, I know,” I said, “you’re a cheap bastard,” and we both laughed.

“It’s not that,” he said after a pause, “it’s just that—well I know we should be hiring for what the company is going to look like in six months but what if it turns out I have to fire them down the line. What if I’m ahead of the game?”

I told him: “You’re at that point when, if you don’t hire enough firefighters, you’ll never get out of firefighting mode.”

“This little start-up of yours,” I continued, “is about to become a company.”

And he looked at me with a mix of relief and sheer terror—and just a touch of nausea.

Later that week, I got an email from another client returning from a board meeting.

“We’re not dead,” he said in a slight nod to Monty Python. They’d given him one more quarter before they’ll decide if they’ll fund that last half million everyone thinks will take the company to break-even. Of course the problem is this is the third “half-million to break even” the company has needed in the last year.

Still another client calls. He’s preternaturally calm. Spooky, even.

“Well my man…we’re burning a quarter million a month and I’ve got a million in the bank. If we don’t close this deal [a deal that will net the company a few million as the result of a sale of an asset], then it’s all over.”

But then he says the really spooky thing; he says: “I think.”

When do you know it’s time? When do you know it’s really time to start the business, shut the business, expand the business, invest in the business, quit your job, end the job search and take the offer on the table, leave your spouse, marry your girl/boyfriend, move to Australia, come home from Australia? When do you know?

“A warrior accepts,” writes Pema Chodron in Comfortable with Uncertainty, “that we can never know what will happen to us next. We can try to control the uncontrollable by looking for security and predictability, always hoping to be comfortable and safe. But the truth is that we can never avoid uncertainty. This not-knowing is part of the adventure. It’s also what makes us afraid.”

I think the only answer to the plaintive poignant question of “When do you know?” is embedded in the bit of Buddhist wisdom: You can’t know–not really, anyway.

Maybe the hardest part of leadership—be it leading a company, a family, a relationship or simply your own life—is that often times you don’t know and you still have to act. Leadership in some ways is built on learning to be comfortable with not knowing, with imperfect knowledge, with the inherent uncertainty of it all.

My mother always said he had massive hair on his shoulders from carrying blocks of ice up the stoops of Brooklyn. As I grew up, I began to doubt that ice causes hair to grow, but I never doubted my grandfather’s strength.

We lived in the ground floor apartment of a three-story limestone (a cheaper version of a brownstone) on East 26^th between Avenue D and Clarendon Road, in Flatbush, in Brooklyn. My grandfather owned the building (as he did several others around the neighborhood).

Dominic (no “k”) Guido, I believed, could do anything. I knew it ‘cause of the rats.

One day, as I was passing through the areaway under the stoop and getting my purple Stingray bike out of the shed to go for a ride, I saw this nose poking through a wall. “Rat!” I screamed and ran out. An hour later, Grandpa showed up. He stuffed the hole with steel wool and broken glass and patched the hole with cement. Rat problem solved. He could do anything.

He also remains to this day my ideal entrepreneur.

He’d left school after the sixth grade. He’d come to America from Palo del Colle in Bari and starting with nothing but a pushcart, he built a mini-empire of two or three trucks (and three or four buildings) selling ice in the summer and coal in the winter (and homemade illegal wine all year long during Prohibition).

He’d made enough money to raise seven kids (some of whom even went to college). And, most important, at the end of the day he always had more money than he had at the start.

I’ve met thousands of entrepreneurs over the years. I get the mindset. I’ve been there, done that; I’ve struggled, celebrated, laughed, and mourned with dozens of them. And when I was an investor, the ones who reminded me the most of my grandfather were the ones I was quickest to fund.

I thought of him, with his gnarled hands, suspenders, perpetually rough cheeks the other day when I was meeting with D.

“At least,” started my client, “at least I can say I raised a lot of money.”

Really? I thought. What would Dominic say?

I get that fund-raising is hard. It’s probably the most frequent topic in my sessions with CEOs. I also remember vividly sitting on a board of a company as it struggled to raise its next round.

But I also remember another client—T. T’s worked at his business for nearly four years.  He’s built his business selling his software product one customer at a time.  This year, he’ll clear $300,000 in revenue and be able to pay himself livable if not great wage as well as the salaries of a developer, a business/sales jack-of-all-trades, and a representative in the UK.

And he has no debt. And he owns 100% of the equity in his company.

Clearly not all companies can be built this way. And clearly, too, T’s business might be able to accelerate rapidly if it had a decent infusion of cash—if for nothing else than to improve his SEO ranking.

Nevertheless, there’s something sweetly endearing about the hand-built, boot-strapped business…something that Dominic would appreciate.

Grandpa’s Rules of Business

1)   Debt? What’s Debt?

2)   Always have a secondary income plan. Sell ice but don’t be afraid to sell a little wine as well.

3)   A nap in the middle of the day is a good thing. A nap at the movies in the middle of the day is a very good thing

4)   Figs are best when eaten right from the tree

5)   Chicks dig Old Spice

6)   Don’t take off your long underwear until the spring.

7)   When in doubt, go ahead and buy the extra truck

8)   Find out what your customer needs and sell it to them

9)    Work harder than your competition

10)   Laugh

11)   Eat lemon drops

12)   Families are good; big families are better

13)   Always remember who you are and where you came from

14)   Always have more money at the end of the day than at the beginning.

I think I’ve finally adjusted to the fact that I’m never going to be a war correspondent. I’m never going to live out of a backpack, drop everything and travel around the world to be where the action is.

I’ve also finally internalized that I’m also never going to spend a few months floating on a river with my best friend Jim. I’m never going to light out for the territories…at least not the way I’d expected. Huck’s learned to close the door softly.

Men at Forty

by Donald Justice

Men at forty

Learn to close softly

The doors to rooms they will not be   

Coming back to.

At rest on a stair landing,

They feel it moving

Beneath them now like the deck of a ship,   

Though the swell is gentle.

And deep in mirrors

They rediscover

The face of the boy as he practices tying   

His father’s tie there in secret,

And the face of that father,

Still warm with the mystery of lather.

They are more fathers than sons themselves now.   

Something is filling them, something

That is like the twilight sound

Of the crickets, immense,

Filling the woods at the foot of the slope   

Behind their mortgaged houses.

When I wrote about disappearing into the fire, I spoke about the emotional burden of being an entrepreneur. But David, and others, eventually wrote about the burden of not being an entrepreneur, of not doing what’s been in the hearts for years.

One woman wrote about the sense of time being wasted, of the dream deferred drying up like a raisin in the sun (I’m feeling the poetry today.)

We all feel it, men and women: the poignant pain of closing the doors on the dreams. And yet, some rail, some fight back, some fight on.

“How do you know when to give it up?” one reader asked, plaintively. He’s worked for years on the system, the implicit architecture. He knows—with absolute certainty—that if adopted, his architecture will radically and inalterably change the way we all interact with information. He knows with the same certainty that he knows his name, knows the way his kids smell after a bath, or the way their laughter drifts down the hall after they’ve supposedly gone to bed, gone to sleep. He knows. But no one will fund it.

I tell him that the most difficult obstacle seems to me that there are simply no investors in the idyllic community he lives. And he knows that’s true; knows it better than I do.

I tell her that as much as she believes her vision to be true, it won’t work unless she has the capital to fund it. And she wants to know why lesser ideas get funded when hers languishes.

And I tell them both that I can’t tell them when they should give up. Only they can answer that question.

Pulling back, I think about my own dreams—those realized and those deferred. I think of Jung and his notion of unlived lives…and how each  of us faces the realization that there are aspects of us which must, simply must, be realized, be lived if we’re going to rage against the dying of that light.

When we find ourselves in midlife depression, suddenly hate our spouse, our job, our life—we can be sure that the unlived life is seeking our attention. When we feel restless, bored, or empty despite an outer life filled with riches, the unlived life is asking for us to engage. To not do this work will leave us depleted and despondent, with a nagging sense of ennui or failure. As you may already have discovered, doing or acquiring more does not quell your sense of unease or dissatisfaction. Stuffing down these rogue feelings or dutifully serving your life’s routines will not suffice. Neither will “meditating on the light” or attempting to rise above the sufferings of earthly existence. Only awareness of your shadow qualities can help you to find an appropriate place for your unredeemed darkness and thereby create a more satisfying experience. To not do this work is to remain trapped in the tedium, loneliness, agitations, and disappointments of a circumscribed life rather than awakening to your higher calling.” Robert A. Johnson and Jerry M. Rhul, Living Your Unlived Life.

For David, for the woman, for the others…walking into the kiln is living that unlived life; it’s awakening to that other life that’s out there, beyond the ennui. Yes, the emotional burden of being an entrepreneur is high–just as high as  the cost of not disappearing into the fire.

Maybe it was the stale pastry. Maybe it was the lack of sleep. Whatever it was, though, when I heard my fellow board member say it, I felt like puking. “What we need,” he bloviated, “is a ‘world-class’ CEO.”

There it goes again, I thought, the myth of a new CEO as silver bullet. Too often we fall prey to simplistic, infantile thinking; we project all of wishes, dreams, and aspirations onto a single person or idea in the vain hope that they, finally, will solve our problems, calm our fears.

In businesses, I’ve seen boards fixate on the act of replacing the CEO. The problem with this is that, in a sense, we doom the incoming CEO to failure. No single person can fix everything.

Management is equally guilty. Sometimes a CEO, facing a monthly burn of a half a million dollars, will fixate on the one mega deal with the big Fortune 500 company (“and they’re thinking of investing as well!!”) as the solution to business model challenges. Magical thinking.

Even more troublesome, the myth often is built on an almost willful ignorance of the facts. If the CEO (or head of sales or head of marketing or CTO) really needs to be replaced—and, believe me, I know that that is often the case—then the troubles don’t end with that one person. If the CEO needs to be replaced, perhaps the whole team she built needs to be replaced as well. Or, even more insidious, perhaps the underlying business model is wrong.

Why do we do this? (And trust me, I’ve done this.) I don’t think it’s because we’re mentally lazy. I think we’re afraid to face the larger implications. When I was investor, it was often because I was afraid to admit I’d made a mistake in making the investment. Or we might be afraid to do the real work necessary to correct the underlying problem (like fire everyone, strip the business down to the barest minimum, and rebuild the business model—I once sat on a board where the CEO (the CEO!) drove just such a decision. It was scary and beautiful.). Or, even more frightening, to face the fact that the enemy, as Pogo said, is us; that the problem isn’t the CEO, or the head of sales, or even the business model but the board of directors.

Real leadership requires putting aside guilt and shame and facing fearsome facts. It would be lovely if a single magical bullet could kill the Werewolf. In business, indeed in life, there’s little room for magical thinking. As Fred Wilson’s former partner used to say: “Hope is not a strategy.”

And the myth of the silver bullet CEO is exactly that: hope as a strategy. In fact, it’s particularly deadly because it’s hope wrapped in the patina of lofty-sounding terms such as “world-class.”

There’s a place in our lives for magic and mythic heroes; just not in the board room.

The ease with which they finished each other’s sentences, completed each other’s thoughts was so graceful, seamless that they could have been sisters. They’ve worked together for years and as they sat on the couch in my living room, on that Sunday afternoon, they nervously fingered the agenda they’d brought.

It was a list of the issues they’d wanted to discuss, a list of potential solutions to their problem. They’d wanted feedback on their proposed solutions. They wanted to remain positive.

“Okay,” I said, “but before we go to the solutions, can you tell me about the problem?”

The eyed each other, paused. K turned to L: “Go ahead. Tell him about the article in the Times.”

An article about a rival organization had come out on a Saturday.  L had read it and understood how the Times had positioned the rival as moving directly into their space, becoming even more competitive. But that wasn’t the problem. The problem was how her boss would take it. She knew he’d go ballistic. But, drained from the years of withstanding his tirades, she finished her coffee and did nothing.

She paid for that coffee on Monday morning. The boss came storming into the office, blowing past all of L’s staff, and started screaming at her. He was angry that the Times had gotten it so wrong. He was angrier still that L hadn’t jumped all over this “problem” and alerted him over the weekend. He was angriest that his board members were concerned and had emailed him. He had been unprepared and he was furious.

Of course this wasn’t the first time. It was a long-standing pattern. But K and L wanted to be strong women. They didn’t want to complain. They wanted to find a solution. They wanted to see what I could help them dream up in terms of changed structures or changes in the way they respond to get their boss to stop yelling.

I said, “Other than in case of fire, there’s no excuse for yelling.”

They were shocked. I repeated my line, adding, “If a friend came to you to tell you that their spouse was hitting them, would you sit with them and concoct ways to make sure the spouse didn’t get angry? Abuse is abuse—plain and simple.”

We’ve all worked with bullies and, unfortunately, in the business of early-stage businesses—where so many companies are run by founders and funded by investors—there are a lot of bullies out there.

I was 13. Living in Gravesend, Brooklyn. My bully was named Sal Quartucci. He was a bit of a manic, hyper Chihuahua-type of kid He’d hope around, spit out his ideas for cool things to do, and try to get you to agree with him. One summer night, we were hanging out in front of Sts. Simon and Jude church on Avenue T when Sal got a bright idea. He wanted to cross McDonald Ave.  to “beat up the Jews.” We lived on Italian side of the avenue and there was a fairly large community of Orthodox Jews who lived on the other side.

I was disgusted. I was afraid. I was pissed. Mumbling something about the whole thing being stupid, I turned to go home. Sal leapt in front of me, calling me a faggot, a pussy, for not wanting to be up some old Jewish guys. I pushed past him and he ran in front of me. Again, goading me, hounding me. Suddenly, scaring the crap out of myself, I grabbed his shirt, threw him down on the ground, punched him the nose. I can still hear the crack and still see the blood on my hand. Our friends pulled me off him and I ran home, shaking.

I thought of Sal as K and L told me of the bullying, the screaming, the berating they’d withstood for more than ten years. Part of me wanted to deck their boss but I searched my head, my experience, my heart for advice on how to respond to them.

I then thought of M.

M and I started working together only a few weeks ago. At the December board meeting, one of his board members—his core investor—told him his job was on the line. This investor had put a few hundred thousand dollars into the company 18 months before. It was a first round, and it’d be combined with some friends and family money. This was M’s first business, his first time as a CEO.

There’s nothing inherently wrong about an investor or director expressing their view that the company may be failing, that the CEO may be failing. Indeed, their implicit responsibility is to identify problems in advance.

But what made this bullying was the style. No warning. No discussion. In fact, the month before the same director had told M that he was the best first-time CEO he’d yet worked with. It was the whiplash that was so troublesome.

In our first session, M and I worked through some of his options. When he called for his second session, he surprised me.

He’d gone to lunch with the director and confronted him.

“When you said that to me, “ he reported he told him, “It had the opposite effect of what you’d wanted. Instead of focusing me, and challenging me, you scared me. All I could think about for weeks was what a terrible job I was doing. How does that help our shareholders?”

I was thrilled. “What’d he say?” I asked.

“He apologized. He told me I was right. And then we started talking about the challenges to the business model.” In the end, confronting the director changed the whole dynamic.

A few years ago, a VC friend of mine called me about one of his portfolio company CEOs. The young man is brilliant, innovative, brash and terrific at fund-raising. In some ways, a VC’s dream but he’s also unpredictable, impulsive and a screamer.

I sent the VC  a copy of Michael Maccoby’s HBR article, Narcissistic Leaders: The Incredible Pros, the Inevitable Cons.

“That’s him,” the VC emailed me, “that’s the CEO. What do I do?”

Maccoby recommends getting the leader a “trusted confidante,” someone who can pierce the narcissism with a straightforward “Cut the shit out.”

I shared the suggestion and added that this guy could use coaching—probably even therapy.

K and L sat quietly as I talked about possibly talking to the boss (as M had done). I suggested trying to engage a board member—we rejected that thought because the boss is so paranoid.

I suggested the Maccoby’s “trusted confidante.” The guy had fired everyone who could play that role.

I suggested trying to implement 360-degree reviews so the board—which is no doubt fully aware of this guys antics but for a variety of reasons unwilling to confront him on his behavior—would have no choice but to deal with it.

In the end, though, I was frustrated. I had little to offer them. I could counsel them, help them get through the week, help them deal with the residual fall out of these tirades but there was nothing they could do to change this guy’s behavior entirely. They could build little coping strategies but they were not going to change this guy.

As they got up to leave, they thanked. ‘This was so helpful,” one said.

“Why?” I asked. “We didn’t really change anything.”

“But we did,” they explained. “You helped us realize this isn’t our fault.”

I realized then beyond making dysfunctional organizations more dysfunctional, beyond getting in the way of actually executing on the business at hand, the true cost of bullying is the damage it can do to one’s self perception. And that’s the real tragedy.

The late afternoon, mid-winter sun had already begun setting. My office, normally bright when the sun is high in the sky, took on a warm, almost eerie glow. As the sun set, he seemed to slink even further into the couch. Head back, legs thrust out in front him, he looked exhausted.

He sighed out: “I’m dreading tomorrow’s board meeting.”

Oy vey, I thought. We’re going to have The Board Discussion.

“Okay…what’s so dreadful about your board meetings?” I asked.

“They’re terrible. There’s no interaction. It’s just like two hours of reporting in—even worse. It’s two hours of me reviewing documents that they’ve all had for a few days and, of course, which none of them have read.”

“So your board meetings suck,” I said. And then, after pausing, I added, “And whose fault is that?”

Okay…enough of my over-written drama…if your board meetings suck, whose fault is it?

I’ll stipulate that investor directors and other board members can be infuriating. In fact, I can see myself writing a bunch of posts on the topic in the future. I’ll stipulate that there should be some general rules of decorum and efficiency that every board member should follow. These include (but aren’t limited to):

• Read the Materials.
• Understand what the company actually does and what market it’s in.
• Pay attention.
• Don’t fall asleep (and this from a guy who did famously once fall asleep albeit during the eighth hour of a ten hour board conference call. Oh, and the meeting sucked.).
• Resist the ADD-inducing distractions of laptops, smart phones, dumb phones, radios, TVs or any other “device.”
• Show up. On Time. And stay until the end.
• Do only one meeting at a time (I know one guy who “attends” one board meeting by phone while sitting, physically, in another).
• Assume management knows what they’re doing until proven otherwise.
• Assume management and staff know more about the day to day activities of the company and its efforts than you do.
• No biting.
• Keep the blowhard opinions down to one per hour and no repeating of someone else’s blowhard opinion.
• Be polite.
• Keep your anxieties to yourself. Just because you’re having trouble with your fund doesn’t mean the CEO should be fired.
• Don’t assume because you’ve had five portfolio companies try and fail before that this company will also fail.
• Share your experience and knowledge.
• Don’t fall in love and be blinded to the realities of the strengths and weaknesses

I could go on…

All of the above may be true about your particular board but that doesn’t mean the board meetings have to be dreadful, boring, or useless.

So here’s my quick set of suggestions for making the board meeting effective:

1. Set and KEEP to the agenda. If the meeting is slated for two hours, take no more than two hours (or less if possible).
2. Get the materials into the hands of the directors at least two days before the meeting (sometimes even earlier if a director requests it).
3. Keep the re-vamping and re-writing of materials after they’ve been distributed to an absolute minimum. Nothing is a bigger waste of time than having board members trying to discuss a point when they have different “facts.”
4. Get the math right. Egregious errors sow seeds of doubt about everything you assert.
5. Do not read the slides. Assume your directors can read (both what’s on the screen and what’s in their hands).
6. Better yet, skip the slide show. Nothing spells disaster than a few pounds of pastries, a darkened room, and someone reading slides. ZZZzzzz.
7. Don’t assume your directors know nothing about your company and your market. Conversely, don’t assume your directors know everything about your company and your market.Ask questions.
8. Be open to suggestions. Don’t be defensive.
9. Tell the truth. No snowjobs, sandbagging or other forms of lying.
10. Have a firm idea of the purpose of a particular meeting. In addition to a general periodic review of the company’s performance, use the meeting to engage the brains of your directors. Formulate a question or questions that will tease out the key strategic challenges you’re facing.
11. Close the meeting with each person having a clear sense of where the company is, what it’s most immediate upcoming challenges are, and—if possible—what the best ways they might be able to help.

In the end, you have to remember that one person has to run the meeting. You may have a chairman and, if you’re lucky, they’ll have the experience and temperament to manage the meeting, facilitate the dialogue, and keep everyone on track. Usually, for start-up companies with tiny boards of directors, that role falls to the CEO.

Got other ideas about making board meetings more effective?