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How to Manage Your Boss

How you lead your leaders is just as important as the guidance they give you.

(originally published by Booz & Company)

Photograph by Steve Cohen
Florida’s first baby of the 1995 New Year tipped the scales at just four pounds and had inherited her mother’s addiction to cocaine. Pictures of the unfortunate infant were on the front page of the state’s newspapers, and the local press could not leave the story alone. To the dismay of Shirley Silverman, a local public health official, neither could her boss, the mayor of the city in which the child was born. In the aftermath of the event, he proposed a new get-tough approach to the problem of maternal drug use and addicted newborns, which included arresting women who used drugs during pregnancy. Ms. Silverman was aghast because she felt that such a policy, far from solving the problem, would drive it underground, making the situation much worse. But her boss, with the press on his back, was committed to his strategy, and she knew that she could not disagree with him either openly or directly without finding herself in an untenable situation. She agonized over what she should do next.

Shirley Silverman’s problem, one of nine mini-cases from Joseph L. Badaracco, Jr.’s new book, Leading Quietly: An Unorthodox Guide to Doing the Right Thing, is that she has to make her boss feel powerful and effective while moving the organization in the direction it needs to go. And that direction is the opposite of where her boss wants to take it.

The John Shad Professor of Business Ethics at Harvard Business School, Professor Badaracco is only one of several scholars and journalists who have recently taken on a challenge that pervades organizational life but has hitherto received scant attention from those who study management. The challenge is managing up — developing a meaningful, task-related relationship with one’s boss. Now the subject is attracting a good deal of attention in books and newspaper columns, in executive education, and on the Web. (Also see “Diary of a Change Agent,” by Art Kleiner, s+b, Third Quarter 2002.)

Professor Badaracco describes the multiple dimensions of the Florida quandary: an intractable problem laden with emotion and bedeviled by racial issues, diverse personal and community interests with people working under a variety of different constraints, and so on. Ms. Silverman buys some time by talking with the mayor’s political advisors, highlighting in graphic detail the political risks of how the get-tough policy might play out in the press. Within days she finds herself heading a task force that has six months to grapple with the balance between law enforcement and caregiving. This gives her the opportunity to reorganize her department so that more of her people can get out into the community. After 10 months, she crafts a compromise that addresses the major issues and factions involved, and infant mortality figures stop rising. Gradually, the political heat dies down. Of course, the fundamental problem of pregnancy and drug addiction does not go away — its root causes lie deeper still — but its symptoms are now manageable, and Ms. Silverman has new confidence in her competency as a quiet leader.

In the view of Professor Badaracco, Shirley Silverman’s quiet leadership is not only the antithesis of traditional heroic leadership, but is far more pervasive and much more effective. Quiet leadership is practiced by thousands of managers who grapple with the quotidian realpolitik of organizational life with restraint, modesty, and tenacity. Chapter headings in the book summarize the author’s helpful messages to managers — “Trust Mixed Motives,” “Buy a Little Time,” “Invest Your Political Capital Wisely,” “Bend the Rules,” and “Nudge, Test, and Escalate Gradually.”

Another writer who uses mini-cases to explore the realities of the leader–subordinate relationship is Carol Hymowitz. Regular readers of her Wall Street Journal column, In the Lead, will be familiar with the many predicaments in which people in business find themselves when their strategy or solution to a problem differs radically from their boss’s. Ms. Hymowitz’s columns are drawn from the operating experiences of real executives, and she does a fine job of compressing practical wisdom into short but memorable tales that resonate with managers at all levels.

One of her recent columns was titled “When You Disagree With the Boss’s Order, Do You Tell Your Staff?” Conventional management wisdom requires subordinates, even when they strongly disagree, to comply without a hint of dissent, lest the organization’s commitment to the decision be seen as wavering. Ms. Hymowitz suggests that there is a new breed of executives who are impatient with this dogma and will ask to know the reasons behind the decision so that the logic (if any) can be explained to their staff.

In another column, “How Managers Can Keep from Being Ambushed by the Boss,” Ms. Hymowitz suggests ways that managers can avoid being presented with irrevocable decisions that affect them and their work. Being able to do so requires, ideally, a trusting relationship that allows the boss to feel comfortable raising any topic directly. Failing that, a subordinate must be sensitive to the often subtle cues from the boss that something is going on. A slew of closed-door meetings to which one is not invited, for example, clearly requires a probe of one’s boss to find out if there is anything one should know.

In contrast with Joseph Badaracco and Carol Hymowitz, Michael Useem, in 2001’s Leading Up: How to Lead Your Boss So You Both Win, uses a series of longer stories to illustrate the exemplary “dos” and cautionary “don’ts” of handling one’s bosses. Whereas Harvard’s Professor Badaracco starts with a framework of advice, and uses short stories to illustrate it, Michael Useem, a professor of management at the University of Pennsylvania’s Wharton School, tells the tales and draws the moral principles for bosses and subordinates as he goes along. All the stories deal with boss–subordinate relationships, and several of them are intrinsically interesting. For example, on an expedition to ascend Mount Everest in 1996, a group of climbers who have paid as much as $65,000 each to be guided to the summit become overly dependent on their “bosses,” the expert mountaineers who are guiding them. When the weather closes in, the top-down instructions, which no one has thought to question, prove inadequate for the climbers in the chaotic conditions. Eight climbers die, largely because their bosses not only didn’t follow their own rules, but, as it turns out, also compromised their followers’ ability to take independent action.

By just reading this and other stories in Professor Useem’s book, one can gain a good appreciation of the kind of behavior that allows an effective subordinate to consistently lead his or her boss to add value to the enterprise. 

However, Professor Useem’s use of long stories demands considerable patience on the part of the reader to stick with the narrative without knowing when the “lessons learned” payoff will come. In what was perhaps a well-intentioned attempt to take the burden off the reader and make the lessons more explicit, the author created 50 teachings that appear in boxes throughout the book. Unfortunately, these are couched in lofty prose, and they function rather like those annoying “wizard” assistants in Microsoft Office programs. Just as you are getting into the task, up one pops with some obvious comment.

In the middle of a story about David Pottruck as president of the Charles Schwab Corporation (he was named co-CEO in 1997), we are told: “The first step in winning the support of your boss is to make sure that your plan is thoroughly analyzed and fully developed. The second is to communicate carefully why the proposed course of action is necessary for the organization and how it can be accomplished with the minimum upheaval to process and employees.” This seems a rather bland, unhelpful conclusion after an immersion in a real-life business situation, where thorough analysis is rarely possible except in hindsight.

Professor Useem emphasizes the individual and his or her relationship with the boss(es) and downplays the context in which they find themselves. As a result, he sometimes gives the impression that he is second-guessing the people on the ground. For example, he relates the harrowing account of the hapless United Nations peacekeeper General Romeo Dallaire and his forlorn attempt to preempt the genocidal bloodbath in Rwanda in 1994. Organizationally, it’s the classic story of the inability of the giant, labyrinthine, notoriously intractable U.N. bureaucracy to sense and respond fast enough to an apparently distant but fast-moving threat. Professor Useem appears unsympathetic to these constraints, however, and focuses relentlessly on what General Dallaire ought to have done: “Even if your superiors reject your appeals or offer little guidance, you must make your own decisions for achieving the organization’s mission. The decisions must transcend the personal resentments that might otherwise get in the way of an unswerving focus on the ultimate aims of the enterprise. If your decisions serve the mission, they will ultimately serve your superiors as well, however shortsighted their perspectives may be at present.” That’s all true, but it’s terribly abstract, and it’s unclear what General Dallaire would or could have done differently with that knowledge.

A revolutionary approach, in which managing up is a way of living rather than a set of techniques, comes from Jack Stack in his new book, A Stake in the Outcome: Building a Culture of Ownership for the Long-Term Success of Your Business, written with Bo Burlingham. Mr. Stack has become something of a hero in American management lore, and his company, the SRC Holdings Corporation, is a management magnet, drawing executive pilgrims from all over the world. He and the company are the best-known advocates and exponents of so-called open-book management, which requires workers at all levels to behave — and think — like owners. (See “Jack Stack’s Story Is an Open Book,” by Art Kleiner, s+b, Third Quarter 2001.) 

The philosophy behind the success of SRC is more radical than it appears: Employees may consent to being managed, but owners will not; as a result, many standard management techniques have to be reexamined. Indeed, in the topsy-turvy world of an open-book company, the organization chart would probably have to be drawn upside down. The frontline workers would be at the top of the chart, and the senior management would be at the bottom. The workers, who are closest to the customer, manage “down” to get the resources they need to keep customers happy and to exploit new opportunities. Senior managers have to manage “up” to support their frontline operators.

The greatest challenge is how to change employees into owners. Mr. Stack recounts briefly the crisis conditions that catalyzed SRC’s birth. With a debt-to-equity ratio that reached 89:1 at its peak, SRC managers learned fast, and the adaptive habits they acquired eventually became virtues. They developed, for example, the routine of having weekly “huddles” to facilitate communication up and down the organization. In such a context, managing up (as well as down) occurs spontaneously.

Ownership, however, cannot be “given” — it has to be taught, and that involves changing habits of a lifetime. Teaching ownership is neither easy nor a one-shot deal. It necessitates repetition and the creation of feedback links between what every individual does and the overarching goals of the organization. Only when individuals feel part of a shared web of cause and effect can they behave as owners, continually improving their routines and fixing things long before they break.

For example, Jack Stack emphasizes the importance of management development, but in a context where every “man” can become a manager only of “himself.” He believes that people learn best informally, from experience — from their daily work activities and their interaction with each other. The challenge is to create the contexts so that these events lead to learning. He says that he has a hard time getting this view across: “People who want to understand the success of our management system … focus on the design of a bonus program. … They think it’s about finding the right kind of incentives. Wrong. It’s all about leveraging the informal training process, using the regular routines of the company to promote continuous learning” (his emphasis).

The greatest appeal of this book, just as of Mr. Stack’s previous effort, The Great Game of Business, is its from-the-trenches authenticity. His bosses, peers, and workers are not logic machines but flesh-and-blood creatures with visceral likes and dislikes. Their emotions, which are so critical to fueling the processes that make for a successful business, also produce toxic emissions that can quickly poison the system. The great advantage of an effective open-book enterprise is that it can harness and use these energies while minimizing their dangerous by-products, or, better still, turning them into productive activities.

One feels that the Harvard ManageMentor Module: Managing Upward is not likely to be used at SRC anytime soon, for it epitomizes the instructional model of teaching that Jack Stack finds to be less effective for learning. The “module” is an HTML-based downloadable product that includes several articles on the topic from the Harvard Business Review. The module itself consists of a series of concepts, steps, tips, tools, and tests.

As a basic checklist, the advice is hard to quarrel with — develop a relationship with your manager, manage expectations, be honest and dependable, be open and receptive to feedback, and so on. But in the context-free setting, the impression given is that organizations are places where rationality rules and clarity is there for the asking — where people know what they want and can say what they mean. The result is a form of counsel filled with verbs that sound like action but really represent desirable outcomes. The reader is left none the wiser about how to achieve them.

The best value in this package is probably the Harvard Business Review piece “Managing Your Boss,” by Harvard Business School management professors John J. Gabarro and John P. Kotter. This landmark article was first published in 1979; its 1993 update is presented here. The article is based on research by the authors that showed that effective managers were successful not only in working downward, but also in interacting with their peers and superiors.

This article, as well as Jack Stack’s new book, is a reminder of how restrictive our conventional definitions of organizations can be, especially the arbitrariness of our characterizations of “up” and “down.” In the complex web of relationships that makes up every organization, management is required in all directions. The ability to work effectively in this way is captured by many of the 360-degree feedback instruments now on the market that require a manager to be rated by bosses, peers, and direct reports. The resulting assessment defines the gap between the actual and desired behavior and sets the scene for the feedback so essential to learning.

But for the feedback to be effective — timely and specific — the learner must be immersed in a compelling context where he or she has to act and respond to others. The Center for Creative Leadership, headquartered in Greensboro, N.C., is one of the most highly rated exponents of this immersion approach, ranking at the top of Business Week’s annual assessment of executive education programs. (The range of the Center’s resources can be viewed at The Center uses a three-phase teaching dynamic of assessment, challenge, and support. Assessment is used to measure the size of the performance gap to be bridged. Challenge consists of “stretch experiences” that create the disequilibrium needed for change — they combine experimentation and practice with intensive feedback. Support is usually best provided by other people — friends and colleagues, coaches and mentors — who can sustain the motivation and help the learner deal with the pain of change.

Managing up may have been neglected for a long time in business literature, but it seems to have always been an essential component of good management. Now it is becoming a skill that can be measured, learned, and even taught.

Managing Up Resources
Works mentioned in this review.

Joseph L. Badaracco, Jr., Leading Quietly: An Unorthodox Guide to Doing the Right Thing (Harvard Business School Press, 2002), 201 pages, $25.95.

Carol Hymowitz, “When You Disagree With the Boss’s Order, Do You Tell Your Staff?” Wall Street Journal, April 16, 2002,

Carol Hymowitz, “How Managers Can Keep from Being Ambushed by the Boss,” Wall Street Journal, April 9, 2002,

Jack Stack and Bo Burlingham, A Stake in the Outcome: Building a Culture of Ownership for the Long-Term Success of Your Business (Currency Doubleday, 2002), 272 pages, $24.95.

Jack Stack and Bo Burlingham, The Great Game of Business (Currency Doubleday, 1994), 252 pages, $17.95.

Michael Useem, Leading Up: How to Lead Your Boss So You Both Win (Crown Business, 2001), 324 pages, $25.95.

Harvard ManageMentor Module: Managing Upward:, $14.95.

Center for Creative Leadership:

Reprint No. 02311

David K. Hurst,
David K. Hurst, a regular contributor to strategy+business, is the author of Learning from the Links: Mastering Management Using Lessons from Golf (Simon & Schuster Inc., Free Press, 2002). A speaker and writer on management, Mr. Hurst also wrote Crisis & Renewal: Meeting the Challenge of Organizational Change (Harvard Business School Press, 1995) and was a visiting scholar/practitioner at the Center for Creative Leadership in Greensboro, N.C., in 1998–99. His writing has appeared in Harvard Business Review, the Financial Times, and other leading business publications.
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