Chapter Six: Bend the Rules

Chapter Six: Bend the Rules

Bending the rules isn’t something we associate with responsible leadership. If anything, it’s what politicians do, or devious lawyers, or kids trying to get around a curfew. Real leaders, according to the conventional view, obey the law and play by the rules—because they see it as their duty and it sets the right example. They know that when leaders fiddle with the rules, others do the same.

Yet things are often more complicated. Consider, for example, telling the truth. This is something we are all supposed to do, but we also recognize exceptions to this rule. Some are trivial: You may decide not to tell a friend what you really think of her new scarf. Other exceptions are profound: During World War II, some families in Europe hid Jews from the Nazis and lied about it.

Between the trivial and profound cases are countless everyday situations in which strict adherence to the rules may do more harm than good. The basic problem is that no one is smart enough to throw a net of rules over all the possibilities—the world is simply too varied and fluid, too ambiguous and uncertain. Hence, we inevitably find ourselves in some situations in which the rules don’t apply and others in which following them is a mistake or even a cop-out.

Quiet leaders respond to these ambiguous situations in a particular way. They are reluctant, for a variety of good reasons, to break the rules, but they don’t want to obey them mechanically and cause harm. So they look, imaginatively and creatively, for ways to bend the rules without breaking them. And, when they find a way to bend the rules, they seize the opportunity and use it to uphold their values and commitments.

But bending the rules is a tricky business that involves walking some very fine lines. To understand why, we will look at a situation that involved a volunteer, a homeless boy, and a frightening, late night subway ride.

A Night in Hell’s Kitchen

Nick Russo, a community service volunteer, and Jerome, a homeless boy, met early on a Tuesday evening in July in Hell’s Kitchen, an area on the west side of Manhattan long known for crime, prostitution, and police officers who looked the other way.

Russo usually spent Tuesday nights working at the Aimes Center, a shelter for homeless teenagers. Most of his other evenings, as well as his weekends, were consumed by his job as an investment banker. Russo had become a volunteer two years earlier after a friend persuaded him to spend a weekend painting several rooms at the shelter. Soon afterwards, he began contributing both money and time to the shelter, even though every visit saddened and hardened him.

One night, for example, he arrived and found an eighteen-year-old boy lying on the floor, barely able to speak. He had been in a drug-related fight three days before, and one of his lungs had been pierced by an ice pick. A doctor had patched him up, and the boy had felt okay at the time. But, just before Russo arrived, his lung collapsed again, and he was gasping for air. The staff asked Russo to take him to a nearby hospital where, after more than an hour pleading with the doctors to see him, the boy finally got treatment. Russo had met fifteen-year-old boys and girls who worked as prostitutes to support drug habits; sixteen-year-old girls with babies, and nowhere to live; and kids who spent a night or two in the shelter and then fled because their crack bosses had learned where they were.

Russo met Jerome right after finishing the assignment he liked least, escorting a teenager to a city youth shelter. This had to be done when the Aimes shelter was full or when a teenager would not follow the rules. The problem was that the city shelters were overflowing with homeless youngsters, so leaving a teenager there was usually a cruel tug-of-war. In addition, city officials sometimes tried to avoid taking in additional kids, hoping the private shelter would take them back. In these situations, volunteers had been instructed to tell the security guard the youth’s name, hand over a file, and walk out of the office. This tactic would force the shelter to admit the youth, though they sometimes had to spend their first few nights sleeping on the office floor.

One Tuesday night at about ten o’clock, Russo walked away from a city shelter. He felt disgusted, with himself and the system. He had just asked a passerby for directions, when a boy who was sitting against a wall jumped up and said, “I’m going that way. Follow me.” Russo looked at him, surprised and said, “What are you doing hanging around here?”

“Nothin’. Just about to go hang at the games,” the boy replied, referring to a video arcade at the Port Authority Terminal. Russo vividly recalled the last time he walked through the terminal late at night: the smell of urine, the dim light, a teenager sitting against a wall shaking violently from drug withdrawal, and gangs walking around in cool paranoia.

“What’s your name?” Russo asked.


“Don’t you think you ought to be back inside that office?”

Jerome answered, “No, I hate them people, but I got some friends in there that I’s visitin’.”

“Oh, I see,” Russo paused. “How old are you?”

“Fourteen. Folks say I’m, like, short for my age.”

Both of them knew fourteen was a bit of a stretch. Russo didn’t think Jerome looked a day over eleven. He knew right away that Jerome was a runaway in trouble. He had learned from his time at Aimes that street kids started conversations with almost everyone and tried to act cool, even though they were hurting inside. Russo was astonished and appalled to see an eleven-year-old kid out so late, on his own, in New York City. The neighborhood where Jerome was hanging around was a war zone filled with crack addicts, prostitutes, the homeless, and the mentally ill.

Russo knew he was close to breaking one of the basic rules at Aimes. During his initial training, he and the other new volunteers had signed a statement saying they would not work the streets unless they were part of a supervised outreach group. Russo also knew that volunteers had been fired for breaking the rule.

Russo had missed dinner so he asked Jerome if he wanted some food. Jerome said no, but followed him into a Korean Deli anyway. The man behind the counter looked at Jerome and smiled. Like Russo, he knew that Jerome was a sad, smart, manipulative kid. Russo bought himself a sandwich and got two candy bars and an apple for Jerome.

As they walked to the subway stop, he told Jerome about his family and his job. Jerome answered that he wanted to go to Wall Street and make some cash, too. But Russo’s efforts to learn where Jerome lived and who was taking care of him went nowhere.

It was after eleven when they got on the subway. A few moments later, Russo was reminded that “Hell’s Kitchen” wasn’t just a roguish old name kept alive for tourists. A man shuffled into their mostly empty car, sat down right next to them, stared dumbly at his reflection in the window, and then opened a long switchblade knife and placed it on the seat next to Jerome. Although Russo’s heart began beating wildly, he kept talking, didn’t look at the man, and began thinking frantically about how to escape. A minute or so later, the man got up, smirked at Russo as if to say “You were lucky, this time,” and got off the train.

The incident petrified Russo and suddenly the prospect of leaving Jerome on the streets appalled him. For the first time, he told Jerome he was from Aimes—news that Jerome clearly didn’t like hearing. “Yeah, I’ve been to that place,” he muttered. When Russo offered to take him there, Jerome refused. “No, I got to play games with my brother. He’s waiting for me.” But Russo wouldn’t give up, and continued trying to convince Jerome to come with him. Aimes seemed to be the only safe haven for Jerome that night.

For several minutes, he made small talk with Jerome while trying to figure out what to do. When the train stopped a few minutes later, however, Jerome got up. “This is where I get off,” was all he said. “Come with me,” Russo pleaded once last time, but Jerome just winked at him and stepped off the train. Russo never saw him again.


Reflections and Regrets

By most standards, Nick Russo deserves credit for quiet leadership. His work at the Aimes Center came on top of the sixty to eighty hours he put in every week as an investment banker. His volunteer work earned him no points at his bank and meant that he started some days worn out and feeling down. At times, he felt his volunteer efforts were basically futile, but he didn’t quit.

The episode with Jerome made him feel particularly bad. He thought he had made a serious mistake in letting Jerome walk away, but didn’t know how he could have prevented it. What had gone wrong? Perhaps his judgment was off because he was tired or scared by the man with the knife. Perhaps he understood intuitively that there was no way to persuade Jerome to come with him. But none of this made Russo feel any better, nor did the fact that, when he decided not to get off the subway with Jerome, he was following the rules of the Aimes Center.

Russo was judging himself, quite severely, by the heroic standard of leadership. He didn’t do all he could to take care of Jerome. He hadn’t found him shelter, even for a single night. Instead of taking a risk and following Jerome off the subway, Russo sat and watched the boy walk away. The man with the switchblade had almost attacked Jerome—what other predators awaited him that night?

The heroic model is not, however, the right way to think about what Russo did. It defines his problem as straightforward—protecting Jerome and finding him shelter—and suggests that a real leader would have done much more than Russo did. But from the perspective of quiet leadership, Russo did the right thing and handled a very difficult situation in an exemplary way. What Russo did was bend the rules—carefully, judiciously, and responsibly.

During his training, Russo was told repeatedly that volunteers were not allowed to engage in outreach. One reason was that successful outreach required training and supervised experience, which volunteers did not have. Other reasons involved risks to the Aimes Center. The Center could be held responsible if volunteers were injured as a result of their outreach efforts. In addition, a teenager seeking attention might accuse a volunteer of abuse without any witnesses to say otherwise, or a volunteer could seem to be involved in a drug sale. If any of this happened, the shelter’s reputation would become a plaything of the media, and both fundraising and recruiting would suffer. For all these reasons, shelters didn’t need what Russo later called “uncontrolled, freelance yuppies” working the streets.

When Jerome first approached him, Russo could have simply walked away. In doing so, he would have been following the nooutreach rule. Instead, he did something much more difficult and impressive. He spent a couple hours with Jerome, trying all the while to balance Jerome’s clear and urgent needs with his own unambiguous responsibilities to the Aimes Center. In the end, Russo exercised leadership—he bent the rules of the Center, in order to try to help Jerome, but he did not break them, because of possible risks to the Center. Russo was willing to take on the challenge of operating in a difficult gray area, rather than resorting to blind allegiance to the rules or heroic and risky efforts on behalf of Jerome.

The problem Russo faced was the most challenging one we have examined. For example, Frank Taylor’s difficulty with the new server was a matter of money, a big sale, and office politics. The worst consequence Taylor faced was a lower year-end bonus. Jerome’s problem, in contrast, might have involved life and death.

Ethical efforts are often best judged like Olympic diving. It is important to compare what people actually accomplish to the degree of difficulty they face. Russo’s dilemma was a complicated leap from a high platform—he was a volunteer with little experience, he was able to buy only a little time, he was dealing with a street-smart kid, he was operating in dark, menacing circumstances, and he had to protect the reputation of the Aimes Center. Russo might have made a tragic mistake by ignoring Jerome in the first place, and he might have made a tragic mistake by following him off the subway.

Unfortunately, despite this careful balancing act, Russo did not feel good about what he had done. For years, he regretted not doing more to help Jerome—regardless of the degree of difficulty or any other excuse. Nevertheless, Russo had demonstrated real leadership.

Take the Rules Very Seriously

When quiet leaders find themselves in complex ethical dilemmas, they follow two guidelines. One tells them to take the rules very seriously, which Russo did. The other tells them to look, creatively and imaginatively, for ways to follow the spirit of the rules while, at the same time, bending them.

Russo was a serious, thoughtful, law-abiding citizen. He had completed the Aimes Center’s training program and, during his two years as a volunteer, had carefully followed its rules and guidelines. The no-outreach rule of the Aimes Center had dominated his thinking during the time he spent with Jerome. He understood the reasons for it—the need for special training and the problems that freelance outreach could cause for the Center and for volunteers themselves. Perhaps the strongest indication of how profoundly Russo understood the no-outreach rule was his ultimate decision not to break it.

The conviction that laws and rules are there to be understood, respected, and followed distinguishes responsible individuals and quiet leaders from underage drinkers and white-collar crooks. Scofflaws view laws and rules as cobwebs to be swept aside. Quiet leaders obey them because of their strong moral weight. In a democracy, the law reflects the will of the people and the traditions of a society. And, when individuals join organizations, they agree, implicitly or explicitly, to follow its rules and policies.

All the quiet leaders we have discussed took the rules very seriously. Rebecca Olson followed the rules in her handling of the charges against Richard Millar—by consulting with several attorneys regarding the hospital’s obligations to him—even though her strong instinct was simply to fire him. Elliot Cortez believed his company was doing something wrong in skirting federal regulations on marketing prescription drugs. Captain Jill Matthews was incensed because the inspectors had so blatantly and casually thumbed their noses at the rules.

There is a second compelling reason why quiet leaders may be willing to bend the rules but usually stop short of flagrantly violating them: They care about their own self-interest. Violating the law can lead to fines, jail time, damaged reputations, and cameo appearances on the local news. Violations of organizational policy can be career-limiting moves. This is why Frank Taylor was extremely reluctant to violate the ban on old-network connections: He thought other sales reps would use this against him. Elliot Cortez was concerned that, if his company was caught playing games, he might end up getting blamed for marketing drugs for the wrong purposes. When quiet leaders face difficult issues, they take the rules seriously in order to protect their reputations, networks, and career prospects.

Most of the time, taking the rules seriously is the only guideline a responsible person needs. But when situations are complicated, following the rules to the letter can be irresponsible and even lead to unfortunate results. Consequently, quiet moral leaders— like Nick Russo—take the rules seriously while, at the same time, looking hard for room to maneuver.

Look for Wiggle Room

Quiet leaders do not think that rules are made to be broken. They see this notion for what it is: an unethical and shortsighted way to deal with serious problems. But they also know that following the rules sometimes leads to painful dilemmas and harmful results. Then quiet leaders try hard to find or create some room to maneuver, but they also do so within the boundaries set by the rules. In other words, they take the rules seriously, but they also look for wiggle room.

Quiet leaders do this because they understand that life seldom presents challenges and problems in the form of stark, either-or choices. Nick Russo did not want to abandon Jerome, nor did he want to break the rules of the Aimes Center. He knew that both of these were serious obligations. He didn’t want to make good on one of them by failing to meet the other. So instead he simply talked with Jerome, invited him to get some food, and then took the subway with him.

Was this outreach? When he met Jerome, Russo was headed back to the Center, not looking for kids needing shelter. And Russo didn’t approach Jerome; Jerome approached him. True, Russo could have told Jerome to leave him alone. But his initial instinct in talking with Jerome and getting him a meal was simply to find out what was going on. Russo was reacting, as many people would, to the shock of being approached, late at night, by a young child. He was not wearing his “volunteer hat,” nor hatching any plans for taking Jerome to the Aimes Center.

Moreover, the Aimes Center was dedicated to helping teenagers, and they were the targets of its no-outreach policy. While Jerome had claimed to be fourteen, it seemed more likely that he was about eleven. Hence, the no-outreach policy probably did not apply, strictly speaking, to Jerome. Nor did some of the rationale behind it. For example, the policy had been designed to protect volunteers from violence, but Jerome was small and young. He posed no visible threat to Russo.

These may seem to be quibbles or loopholes, but they point to a larger issue. The no-outreach rule was simply a requirement the Aimes Center had introduced, three years earlier, to help avoid certain problems. It wasn’t one of the Ten Commandments or part of the U.S. Constitution; it wasn’t a city or state law; and it didn’t express a fundamental ethical principle, like telling the truth or respecting others’ rights. It was a blanket prohibition, a crude instrument for a complicated world. It hadn’t stood the test of time. In all likelihood, the rule would be modified and refined in the future, precisely because of situations like the one Russo faced.

Moreover, if Russo had ignored Jerome’s first advance, he would have violated another important policy of the Aimes Center. The only time the Center “abandoned” teenagers was when it left them in City welfare offices—which is what Russo had just done. Although such action put young people in the custody of public officials, the Center viewed this tactic as a last resort and a mark of failure. In other words, once the Center had a relationship with a teenager, it did everything it could to help. Wasn’t Russo obligated to do the same with Jerome? By talking with Jerome and going on the subway with him, wasn’t he respecting the basic mission of the Aimes Center, rather than following a recent, untested, internal regulation? In this case, which was more important?

But what if he had left the train with Jerome? At that point, Russo was thinking explicitly about how he could get Jerome off the streets. Following him into the Port Authority Terminal and trying to persuade him to go to the Aimes Center would have been freelance outreach. Moreover, the episode with the knife-wielding passenger demonstrated for Russo the basic rationale for the nooutreach policy. When volunteers broke this rule, they could put themselves in real danger and imperil the reputation and future of the Aimes Center.

So Russo drew a line. He decided that talking with Jerome, buying him a meal, and riding the subway with him only bent the rules, but getting off the train violated them. Should he have done a little less? Could he have done a little more? Those questions cannot be answered with precision—even in retrospect. As we have seen, Russo continued to feel he should have done more, but there’s no way to know what the outcome might have been if he had. In uncertain, fluid circumstances, the quest for final answers is futile. What really matters is the careful balancing of competing obligations. Nick Russo worked hard at this, under extremely difficult circumstances. He performed extremely well in a very demanding test of leadership.

Like Russo, quiet leaders don’t want to impale themselves on the horns of dilemmas. They look long and hard for ways to meet all their obligations and commitments rather than make hard choices among them. Instead of confronting dilemmas head-on, they prefer to use creativity and imagination to work around them. This is what Frank Taylor did to avoid choosing between meeting his client’s needs and following the “Win-Win” policy. Garrett Williams did the same in looking for ways to treat his employees fairly while satisfying his boss’s demand for a quick turnaround.

When people are under stress, their natural tendency is to grab hold of whatever source of security they can find, and security is often found in following the rules to the letter. It takes courage and determination to follow the example Russo set. He took all his obligations to the Center seriously, but he didn’t shirk his duties as a caring human being.

Entrepreneurial Ethics

Most of the time, there is nothing wrong with following just the first of the two guidelines described in this chapter. Taking the rules seriously is usually the safe, smart, and responsible thing to do. If most people didn’t behave this way most of the time, the trains wouldn’t run on time and society would fly apart. In difficult situations, however, both guidelines become important. Following either one can lead to serious problems.

One of these problems is evading responsibility by taking the rules too seriously. Saying simply “These are the rules and I have to follow them” can be a way of avoiding responsibility. Only moral bookkeepers, fitted out with green eyeshades, define ethics as a checklist of “do’s and don’ts.” This may seem responsible, but sometimes it just isn’t. In some cases, as the French moralist La Rochefoucauld put it, “We are held to our duty by laziness and timidity, but our virtue gets the credit.”[1]

For quiet leaders, taking the rules seriously doesn’t mean treating them as a paint-by-numbers exercise. When things get complicated, quiet leaders take initiative, trust their creativity, and work hard to create room to maneuver. They approach ethical problems as entrepreneurs, not clerks.

This entrepreneurial approach often pays big dividends. In part, this is because of the astonishing fertility of the human imagination. The human talent for seeing things in a variety of ways is a valuable skill. Martha Nussbaum, a gifted interpreter of Aristotle’s ideas, has written, “Moral knowledge . . . is not simply intellectual grasp of propositions; it is not even simply intellectual grasp of particular facts; it is perception. It is seeing a complex, concrete reality in a highly lucid and richly responsive way; it is taking in what is there, with imagination and feeling.”[2] Quiet leaders approach problems with the conviction that practical-minded creativity can almost always create new possibilities for responsible action.

Imagination cannot, of course, perform miracles. In one Woody Allen story, he describes sitting in a café and trying to convince a despondent friend that a review referring to a “playwright of absolutely no promise whatsoever” could be interpreted in several different ways. Sometimes situations are black and white and individuals cannot avoid hard choices. Sometimes we have to make good on one commitment or one responsibility and let others slide. But, until their backs are firmly against the wall, quiet leaders search vigorously and creatively for ways to make good on all their obligations.

The other reason imagination often succeeds is that most situations have more levels and greater intricacy than appear at first glance. For example, when Frank Taylor drilled down into his problem, he realized that there were a variety of ways to define what it meant to “connect” a computer to a network. This wasn’t because he was playing fast and loose, but because there simply was no standard, etched-in-stone definition of what computer specialists call “connectivity.” Taylor’s analysis and fact-finding had revealed the complexities of his problem, and this gave him more opportunities for creative maneuvering. In fact, Taylor’s eventual solution to his problem—getting the law firm’s new servers classified as a test site—was itself a creative way of maneuvering within the rules of his company. Without this imaginative recasting of his problem, Taylor would have had to break the rules against old-network hookups or lose an important sale for his company. In other words, wiggle room isn’t just hokum. It reflects reality. The complexities of the world, examined carefully, usually offer room to maneuver. This is why creative, opportunistic approaches to difficult issues often pay off.

But simply following the second guideline and looking for wiggle room can lead to dangers of its own. This is the reason why the first guideline—take the rules very seriously—cannot be forgotten. Imagination needs boundaries, and the laws and rules provide them. Consider the case of a bank robber who walks up to a teller, takes out a vial of cooking oil, says that it’s really nitroglycerin that could blow up the bank, and asks for the contents of the cash drawer. This may be very clever, but it shows what can happen when imagination and cleverness are unbounded by the rules.

Breaking the rules is an easy way out, as is following them robotically. In contrast, bending the rules is hard work. It involves exercising creativity within the boundaries set by the law, the rules, and prevailing ethical customs. It demands discipline and restraint, along with flexibility and imagination. Finally, it requires a measure of faith—faith that difficult, careful judgments about competing obligations will make a difference in the long run.

Russo never learned what happened to Jerome. Perhaps he got into trouble that night, perhaps he found his way to safety, perhaps the concern and compassion Russo showed Jerome made him more likely to go to a shelter or seek other help. The ultimate effects of small things are often unclear. In this respect, they resemble letters, as once described by Emily Dickinson—they are written thoughtfully, addressed carefully, and placed in the mailbox, but no one knows if they are read or received.


Leadership and Cleverness

This approach to ethical situations runs counter to our standard image of what leadership is all about. We prefer leaders who defend their values clearly and forcefully. We associate cleverness, complexity, loopholes, and maneuvering with dubious characters, not role models. Like many other politicians, Ross Perot appealed to this sentiment in his presidential campaigns. One of his favorite phrases was “See, it’s simple,” after which he would compare some longstanding, complex national problem to his car or an old dog.


A better motto is Albert Einstein’s. He said, “Everything should be as simple as possible, but no simpler.” Quiet leaders do not bend the rules casually, nor do they view cleverness and maneuvering as ideal ways to deal with problems. But sometimes the complexities of situations give them no choice. Drilling down doesn’t produce an answer, and they can’t buy more time. They confront situations like the one Russo faced as Jerome walked toward him in Hell’s Kitchen.

So they look for ways to bend the rules without breaking them. They do this after grappling with the complexities of a situation, not as a shortcut around them. Their aim is not to avoid responsibilities, but to find a practical, workable way to meet all of their responsibilities. An imaginative, entrepreneurial approach to ethical dilemmas can often help people avoid heart-wrenching choices and enable them to make good on all the commitments they hold dear.

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