5 Questions to Help Manage Your Toughest Problems at Work

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?

How managers work through gray areas

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.

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.

There are no quick and easy solutions

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.

workplace stress anxiety

Cutting to the core of hard problems

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:

  1. One is that we human beings have a common human nature, because of Darwinian evolution or divine creation.
  2. 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 20 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.

Why are these 5 questions useful?

The five questions are:

  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?

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.

A way to sharpen your judgment

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.

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.

Harver Team

Harver Team

Posted on:
July 25, 2023

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