Resolve Your Toughest Work Problems with 5 Questions

New Book: In Managing in the Gray, Joseph Badaracco offers managers a five-question framework for facing murky situations and solving tough problems.
  • Author Interview

Work through problems as a manager; resolve them as a human being.

Interview by Michael Blanding

In business, as in life, there are few black-and-white situations where all of the facts are in, and the answer is immediately apparent. Some issues, however, are a darker shade of gray than others—it’s those murky problems that Joseph L. Badaracco, the John Shad Professor of Business Ethics at Harvard Business School, tackles in his new book, Managing the Gray: 5 Timeless Questions for Resolving Your Toughest Problems at Work.

“Everybody faces these kinds of problems, where you are really not sure how to get a handle on them,” says Badaracco. “You have to make a decision, and the decision matters. Often, when you’re dealing with gray areas, you may not have all of the facts you need, or you may be unsure of how to frame the problem, or the people you work with may disagree.”

These are the types of problems that land squarely on managers’ desks. “In organizations, the complex, messy problems tend to get delegated upward,” says Badaracco, who has been teaching courses on strategy, leadership, and ethics at HBS for more than 35 years.

For guidance on handling gray-area problems, Badaracco turns not to the latest management theories but to a much older source—a wide range of thinkers, over the centuries, who have wrestled with the big questions of human nature, our common life together, and the soundest ways to make hard, important decisions. Reading Managing the Gray is like being at a board meeting where your fellow directors include Aristotle, Nietzsche, Confucius, and Thomas Jefferson.

Ultimately, however, the book distills their guidance into a single sentence that Badaracco introduces early on in the book: “When you face a gray-area problem,” he writes, “you should work through it as a manager and resolve it as a human being.”

Approaching a problem as a manager means working with others and doing all you can to really understand the problem. “You don’t decide these things in splendid isolation or with brilliant insights. You get data and use the tools you have to analyze it with other people.” In gray areas, however, discussion and analysis doesn’t produce a final decision. Badaracco says that in these instances, “somebody finally has to say this is what we are going to do and this is why, and that takes an act of judgment.”

Badaracco provides five questions that work as guidelines for making gray-area decisions:

  1. What are the net, net consequences?
  2. What are my core obligations?
  3. What will work in the world as it is?
  4. Who are we?
  5. What can I live with?

“Versions of these questions run through so much of the serious thinking about hard decisions that you find in philosophy, theology, and literature,” he says.

Each chapter in the book explains one of the questions, describes why and how it has captivated serious thinkers for so long, and gives practical guidance for applying the question in organizations. The first question, for example, asks you to think hard about the “net, net consequences” of your options when faced with a gray-area problem. The question, often associated with John Stuart Mill, the father of utilitarianism, crystallizes a way of thinking about hard, complex, important decisions that has deep roots in Western and Eastern traditions.

What the question asks today is whether, in the face of a high-stakes decision, you have thought about its impact fully, carefully, and objectively. This means its impact on everyone—not just employees and clients, but all who will be affected, in some cases profoundly, by what you decide.

None of the five questions works by itself. In fact, each question counteracts weaknesses in the others. For example, the question “What will work in the world as it is?” takes its cues from Niccolò Machiavelli, author of The Prince. His name is usually associated with treachery and expediency, but Badaracco emphasizes that Machiavelli’s broader message is to men and women with serious responsibilities to other people. In other words, “If you are taking responsibility for other people, you need to find something that is going to work—and work in a world that is uncertain and politically difficult and treacherous and full of surprises.” In short, idealism and pragmatism have to temper each other.

One of several examples Badaracco presents throughout Managing the Gray is the case of Aaron Feuerstein, the owner of Malden Mills in Lawrence, Massachusetts, the original manufacturer of Polartec fleece. After a major fire in late 1995, Feuerstein vowed that he would rebuild the entire facility, continuing to pay the salaries of his workforce during the transition. As laudable as that commitment was, it eventually led Feurstein to declare bankruptcy, costing all of the workers their jobs.

“Feuerstein believed he had a strong obligation to his workers, which is genuinely admirable, but it looks like he underweighted the analytics, especially around risk,” says Badaracco. Had Feuerstein thought more carefully about the consequences of his decisions on all stakeholders, and how it might play out in the real world, he might have made the decision to rebuild only part of the company, or keep some of the workers on the payroll. “Some people may have lost their jobs, but a lot more might have survived,” he says.

With hindsight, it is easier to pass judgment on Feuerstein’s choices, but in the moment it’s often very difficult to figure out the right course of action. Thinking through the first four questions Badaracco can help dispel some of the gray. In the end, a final decision has to be made.

That’s where the last question—“What can I live with?”—comes in. Badaracco quotes Alfred P. Sloan, a brilliant practitioner of business analysis, who wrote in his autobiography, “The final act of business judgment is, of course, intuitive.” But this is tempered intuition, not initial instinct, Badaracco hastens to add. “It means you decide what you can live with, as a manager and a human being, after and not before you work your way through the first four questions. Only then do you have the license to say, this is my judgment and my best sense of what we should do.”

As Badaracco sees it, in-depth analytical work is the crucial first step in addressing gray-area problems. But it doesn’t dispel the gray. That only happens when someone steps forward and makes a decision, based on his or her judgment, as a manager and a human being, and bases this judgment on the long-standing, powerful ideas described in the book.

  • Book Excerpt

Untying the Gordian Knot

from: Managing in the Gray: 5 Timeless Questions for Resolving Your Toughest Problems at Work
by Joseph L. Badaracco

Gray areas are basically organizational versions of the classic Gordian knot: that is, they are dense tangles of important, complicated, and uncertain considerations. As such, they can be some of the hardest work you have to do as a manager, and they can feel like a serious burden. At the same time, like the Gordian knot, they can be compelling challenges that show you and others what you are capable of doing. According to myth, Alexander the Great became so frustrated with the Gordian knot that he unsheathed his sword and sliced through it but, as a manager, you don’t have this option. So what is the best way to deal with the gray area problems you face?

The Five Questions

The answer, in its shortest form, can be stated in a single sentence: when you face a gray area problem at work, you should work through it as a manager and resolve it as a human being.

Working through gray area problems as a manager doesn’t mean acting like the boss or a bureaucrat. And it doesn’t mean having a particular job on an organization chart. Management is basically an extraordinarily effective way of getting things done, inside and outside organizations. At its core, managing simply means working with and through other people to accomplish something. Approaching a gray area as a manager typically means working with other people to get the right information on a problem, analyze the data thoughtfully and rigorously, and look for practical solutions to problems.

“When you face a gray area problem at work, you should work through it as a manager and resolve it as a human being”

But, with gray areas, this first step isn’t enough. Information, analysis, and discussion don’t resolve the problem. You still don’t know what to do. When this happens, you have to take a second step: you have to resolve the problem as a human being. This means grappling with the problem, not just as an analyst or a manager or a leader, but as a person. It means making decisions on the basis of your judgment—which means drawing on your intelligence, feelings, imagination, life experience, and, at a deeper level, your sense of what really matters at work and in life.

This second step may sound simple, but it isn’t. We often hear that, when we face tough decisions, we should follow our moral compass, emulate a role model, follow the guidance in our organization’s mission statement, or do what passes the “newspaper test” and ask if we would be comfortable seeing our actions reported in the paper, or just do the right thing. But there are no quick solutions to gray area problems. If there were, we would have them on laminated cards in our wallets.

Algorithms can’t solve the hard human problems of life and work. Managers who face these problems have to learn all they can from information, data, experience, and rigorous analysis. Then they also have to think deeply—as human beings—about what they really should do. Resolving gray area problems as a human being means asking yourself the right questions and working hard to develop your own answers. These questions are the indispensable tools for deliberation and judgment. There are five of them, and this book explains them in depth.

Why do these questions help and what makes them so important? In essence, they are the questions that thoughtful men and women have relied on, for many centuries and across many cultures, when they had to grapple with hard, complex, uncertain practical problems. The questions reflect profound insights about human nature, our common life together, and what counts as a good life. Understood fully and used together, the questions are valuable tools for guiding your judgment when you have to make a decision about a gray area problem.

You may be wondering if there really could be just a few questions that actually cut to the core of really hard problems. Why would this be the case? There is no definitive answer but, as you will see in the following chapters, there is a plausible, if controversial explanation. It says two things. One is that we human beings have a common human nature, because of Darwinian evolution or divine creation. The other is that all human communities have confronted the same basic questions about responsibility, power, shared values, and decision making—and converged on the same basic approaches.

There is no single, right way to phrase the five questions. I have spent much of the last twenty years trying to develop useful, practical tools that managers can use when they confront hard issues of leadership and responsibility. The version of the five questions in this book has been refined and tested through countless executive and MBA classes, research interviews, and counseling sessions with individual managers, as well as through research and reading. In the spirit of the great American pragmatist philosopher, William James, I have tried to develop useful, everyday tools rather than universal truths, and a practical bias runs throughout this book.

  • What are the net, net consequences?
  • What are my core obligations?
  • What will work in the world as it is?
  • Who are we?
  • What can I live with?

It is natural to wonder why these five questions would be remarkably useful. The answer is that they have passed a demanding test. It asks if there are ways of thinking about hard decisions that have, over the centuries, engaged many of the most penetrating minds and compassionate hearts when they were searching for the right way to resolve really difficult problems. As you will see, the five questions, expressed in various ways, have engaged philosophers, ranging from Aristotle to Nietzsche; religious leaders, like Confucius and Christ; and political thinkers, like Machiavelli and Jefferson; as well as poets and even artists.

To be clear, this test does not ask whether there is some grand consensus that the great thinkers of history all accept. That would be a preposterous claim. The key question is whether there are some approaches that have consistently engaged many of these powerful, incisive, compassionate minds, when they tried to understand what made for good decisions and good lives. If some ways of thinking have passed this test of history and culture, then they are well worth our time and thoughtful attention.

The five questions are, in effect, important voices in a long conversation about how the world really works, what makes us truly human, and the soundest way to make difficult, important decisions. No single voice in the long conversation gives us a universal truth, but each gives us valuable insights for making uncertain, high-stakes decisions. That is why these questions are such powerful tools for testing, broadening, and sharpening your judgment when you face gray area issues.

What kinds of tools are they? Philosophers, lawyers, theologians, and political theorists can sharpen each of the questions to a fine edge and wield these intellectual scalpels with brilliance. But managers need something different: they need sound, sturdy, everyday tools—like the ones in toolboxes and kitchen drawers. This comparison to tools may seem like a passing metaphor, but it actually reflects a long intellectual tradition at Harvard Business School, which has aimed, for more than a century, to develop important, useful ideas for managers. Professor Fritz Henderson, one of the school’s intellectual pioneers, believed that most useful theory for managers was “not a philosophical theory, nor a grand effort of the imagination, nor a quasi-religious dogma, but a modest pedestrian affair or perhaps I had better say, a useful walking stick to help on the way.”

Reprinted by permission of Harvard Business Review Press. Excerpted from Managing in the Gray: Five Timeless Questions for Resolving Your Toughest Problems at Work. Copyright 2016 Joseph L. Badaracco. All rights reserved.

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