Carolyn 101

Business Lessons from The Apprentice's Straight Shooter

Carolyn Kepcher, Stephen Fenichell

• Publisher: Touchstone
• Year: 2004
• ISBN:
  9780743275170
• Topic: Commerce
• Subtopic: Commerce Général

Known to the millions of viewers of the hit reality television show The Apprentice, Carolyn Kepcher attracted enormous media attention for her cool demeanor and her no-holds-barred assessments of the show's candidates in the boardroom each week. In particular, she was not shy about speaking out about her disappointment with the professional conduct of the female candidates, whom she felt too often resorted to using their sex appeal to move ahead and gain the favor of Donald Trump.
But if anyone knows what to do to impress Donald Trump, it's Carolyn, his longtime employee and trusted adviser. In Carolyn 101, she reveals the secrets of her own success and provides readers with guidance for their professional lives. By looking at the types of people most often encountered in the workplace, she illustrates her advice with examples from her career -- largely within The Trump Organization -- showing readers how to:
• ace an interview
• ask for a raise or promotion
• maintain a healthy balance between work and home life
• deal with a difficult boss
• spot and seize potential business opportunities
• dress for success
• be a strong team member or team leader
Inspirational to both recent college graduates entering the workforce for the first time as well as seasoned employees looking to distinguish themselves, Carolyn 101 will show ambitious professionals what they need to do to get ahead and take their careers even further than they had imagined.

TWO

The Bad Boss

To: Carolyn Kepcher [E-mail]

I know you are a busy woman so I will be brief. I just wanted to let you know that my wife and I enjoy watching you, George and Mr.Trump discuss and make decisions about the contestants and whether they have what it takes to be The Apprentice. I can see that you are one sharp lady. So, I have a favor to ask of you. My boss is making my life miserable for me at work and I don’t know what to do, or who to turn to. At first, he seemed like a perfectly nice man but now he seems to have it in for me. Do you have any words of advice for me before I either quit or report his negative conduct to the president of the company?

Help!

Hail to the Chief

Of all the relationships you develop on the job, the one you have with your boss is by far the most important and, more often than not, either the most taxing or the most rewarding. Sometimes, with a certain kind of difficult boss—the inconsistent one, the most frustrating of all, who vacillates between being supportive and being undermining—it can be both or either, depending upon the day of the week or the phase of the moon. On the very same day that I finally went to work for the best boss of my life, Donald Trump, the irony of my situation was that I also found myself working for the worst boss of my life, Andrew Broderick.

Unless we are fortunate enough to work for ourselves—in which case we often have difficult clients, which amounts to pretty much the same thing as difficult bosses—most of us will face a difficult boss or two (let’s hope not three!) at some point during our careers.

Difficult bosses come in a wide variety of colors, flavors, shapes, and sizes. Based on my own stressful experience— as well as those of friends and colleagues over the years— I’ve learned to break difficult bosses down according to a scheme that can help you develop useful strategies for managing their often erratic, destructive, and compulsive behavior. You may have encountered a number of these characters hovering around your own cubicle or corridor, although I hope not all of them, or at least not all of them at the same time.

1. There’s the Two-Faced Poker Player. You’ve met him before. I’d met him before. In fact, he was the one who just left Briar Hall. He or she is, at bottom, weak, indecisive, and insecure. As a result, he tends to avoid open conflict and prefers to stick the knife in your back. He’s virtually guaranteed to smile and agree with you about just about anything, until you walk out of his office, at which point he’s likely to pick up the phone and denounce you to a colleague as a raving idiot. According to the most recent research on this subject—which is becoming a hot topic at business schools, by the way—the Two-Faced Poker Player is the most common type of bullying boss. Women are just as likely as men to fall into this category, although women are more likely to be the victims of this type of boss’s abusive behavior.
2. 
   
3. There’s the Angry Loudmouth. He or she rants and raves and emulates the management styles of Saddam Hussein, Stalin, or Ivan the Terrible. This type of bullying boss, unfortunately, is a dime a dozen. He is rude and inconsiderate, and unless kept on a tight leash by senior management, as terrifying as a poorly trained attack dog. The Angry Loudmouth gains his power through crude intimidation and wields that power like a blunt battle-ax. He tends not to be very skilled at self-defense, however, and like all playground bullies is at heart both a fool and a coward.
4. 
   
5. There’s the Snide Wisecracker. He or she knows precisely how to reduce you, the victim, to a trembling mass of low-self-esteem jelly with a rapier thrust right into the core of your worst weakness. In the presence of the Snide Wisecracker, you find yourself tongue-tied and inarticulate. The most carefully honed skill of this type of difficult boss is to disarm the victim with a subtle put-down. If you reproach him about the true intentions of his hostile remarks, his defense is always the same: “What? Oh, I’m so sorry! You must have misunderstood me! Didn’t you realize I was only kidding?”
6. 
   
7. One of my personal favorites is the Controller, and I’m not talking about the type who conducts financial audits. This type of difficult boss conducts audits of everything around him that moves, breathes, or can fog a mirror. He or she knows where all the skeletons are buried. He makes a point of keeping tabs on everyone through a network of toadying spies and cronies. He forms alliances easily with those he can manipulate to do his bidding. But if you prove resistant to his wiles, he will make your life miserable. The Controller is the most dangerous of all difficult bosses because his greatest skill is cutting you off from any ally who might be able to help you resist him, even from your ultimate superior, to whom he is terrified you might report him. In situations where the ultimate boss is likely to be reasonable, the Controller is at a distinct disadvantage. He loves playing favorites, currying favor with his superiors, and figuring out all sorts of clever schemes to make you fall flat on your face, if possible spectacularly.

While this typology can be a useful guide to difficult bosses, in my experience difficult bosses frequently mix and match their abusive styles according to opportunity and situation. I’ve learned that the presence of a toxic boss can not only spread fear and terror but so thoroughly demoralize work groups that he or she can practically shut off all function.

Even at Briar Hall, and during the previous six months, I’d dealt with one form of difficult boss: the Two-Faced Poker Player, the indecisive, weak, nonconfrontational type. True to form, Bob Thomas had driven our staff to distraction because he had refused to face up to the fact that just about every situation on earth involving people will involve conflict and that, as a consequence, good conflict resolution is a prerequisite for an effective leader. Bob had avoided conflict like the plague, and he paid a high price for his stubborn denial of the undeniable. As a result, while he focused on painting a room or buying that new popcorn machine for the restaurant, the staff, who should have been looking to him for guidance and direction, began coming to me, which made him feel even more threatened, and made an already difficult situation even more tense and stultifying.

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CAROLYN 101:

You need a strong sense of self to manage a weak boss.

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Good Boss/Bad Boss

Donald Trump—a famously good boss, whose best employees tend to stay loyal to him for decades, unless they betray him and The Trump Organization—closed on Briar Hall in November 1996. He paid roughly $8 million for the property, which turned out—surprise, surprise!—to be a terrific deal for The Trump Organization. He had made good on his promise and brought me along. I had recently turned twenty-five. I was now working in a position of serious responsibility for The Trump Organization. As you can no doubt imagine, I couldn’t have been more pleased with this opportunity—it felt as if I had just won the lottery.

When I returned to the club and pulled into the same space I’d parked in every day for two and a half years (with the unhappy exception of the previous three weeks), I was greeted by a small welcoming committee drawn from the skeleton staff who had stuck around for the off-season. After accepting sincere congratulations from all of them, I headed straight for my old office, hoping that everything would look the same. But, standing in the hallway, I could see a freshly painted name on the door of the general manager’s office, on which I knocked softly.

In response to a bass-toned “Come in,” I tentatively opened the door. The newly appointed general manager of the Briar Hall Country Club stood up to greet me. He was a square-shouldered, square-jawed man, tall and thin, who looked to be in his early fifties. He wore a well-tailored, close-fitting dark suit and sported an expensive haircut. In a thick British accent he introduced himself, and I half-expected him to bow from the waist and kiss my hand. I immediately recognized the type: a proper, polished, British gentleman of the old school. Andrew Broderick made a terrific first impression: he seemed self-confident, engaged, well organized, and enthusiastic.

The gist of our first conversation was that it would be our honor and our privilege to bring the tatty old Briar Hall Country Club up to the most exacting Trump standard. For an indeterminate period of time, he stressed, we would be operating the place as the Briar Hall Country Club while paving the way for the all-new five-star Trump National Golf Club to be constructed on the same site. From the way he said this, I could tell he found it a bit beneath him to be known as the general manager of the pokey old Briar Hall Country Club and obviously preferred to be regarded as the general manager of Trump National. Unfortunately, none of us knew when that transformation was slated to begin, as a number of complicated zoning and regulatory issues still needed to be resolved. But Andrew let it be known, in no uncertain terms, that he had been associated with some pretty prestigious golf clubs, and Briar Hall was not on a par with his old haunts.

Taking an Accurate Measure of Your Boss

So what did I know about my new boss after leaving his office that day? Even more pertinently, what did I know about my new boss that would help me help him achieve his goals, so that we could both benefit from our joint success? I knew, for one thing, that we were both new recruits to The Trump Organization, and that he had only about two months up on me, so we knew approximately the same amount about the company and the people in it. I knew that neither of us had gone through any formal intake procedure or new employee orientation, because The Trump Organization is deliberately kept loosely structured, according to its founder’s desire to minimize bureaucracy and decentralize its business units. The construction projects, the residential and commercial real estate management divisions, the golf courses and resorts, including casinos, clubs, and hotels, all operate with a high degree of administrative autonomy. Donald Trump delegates freely, but if one of his managers makes too many mistakes, it’s the street, not the suite.

It felt safe to assume that both of us had joined The Trump Organization because we were eager to be associated with the very best, in every conceivable style, shape, and form. But as with any other assumption, it was important to analyze this one for possible pitfalls. Although we were both employees of Donald Trump’s, as Broderick’s subordinate, I needed to demonstrate to him that I intended to support him fully in achieving his goals. But the obvious corollary would be that he would, in a reasonable exchange, support me in achieving mine.

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CAROLYN 101:

When you join any new organization, it pays to get an up-close, in-depth reading of your immediate superior. It is also important to give your new boss a nice, clear heads-up on your goals, motivations, skills, and plans.

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Ideally, the manager’s goals, the employee’s goals, and the organization’s goals should be identical and inseparable. But in the real world of egos, tempers, and divergent opinions, the actual goals of individuals and the idealized goals of groups tend all too often to diverge wildly. For example, what does it mean when we say, in a professional situation, that “he or she is in it only for himself or herself”?

We typically mean that this person, for whatever reason, simply refuses to accept the fact that his or her goals can be fused with those of colleagues and those of the organization as a whole. The interesting thing about all the bad bosses I’ve known is that they seem to share the same delusion: that their goals and the goals of the organization/group/team are always divergent.

At The Trump Organization, we have a saying:

“If one of us succeeds, we all succeed. If one of us fails, we all fail.”

Imagine an army in which every soldier’s goals are discordant with those of the leadership. What have you got? A losing battle.

From my new boss’s language in that first meeting, I should have felt confident that he regarded his own advancement as connected to my advancement. I should have felt confident that we were both committed to supporting each other to achieve this marvelous transformation from old Briar Hall Country Club into sumptuous new Trump National Golf Club. But as yet I had only his word to go on. And something about his tone and style did not make me feel confident that he was the least bit interested in supporting me.

So here we were, two rank newcomers to The Trump Organization, both of whom, I could safely assume, were going to be doing their level best to internalize and interpret the justly famed “Trump style” in their own terms. From our first conversation, I received the distinct impression that the Trump style of excellence was going to be, for my new boss, mainly a matter of maintaining surfaces: of shiny doorknobs, clean napery, correct posture, stiff upper lip, and so on.

Not that that was such a bad thing. Personally, I have no problem with this approach. As in any service industry, in the resort and country club worlds, all surfaces that members, visitors, or their guests touch or see should be spic and span and polished at all times. That management discipline needs to be focused on these high-visibility areas or productivity suffers is a well-underst...