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How to tackle your toughest decisions

Every manager makes tough calls—it comes with the job. And the toughest calls come in the gray areas—situations where you and your team have worked hard to gather the facts and done the best analysis you can, but you still don’t know what to do. It’s easy to become paralyzed in the face of such challenges. Yet as a leader, you have to make a decision and move forward. Your judgment becomes critical.

Judgment is hard to define. It is a fusion of your thinking, feelings, experience, imagination, and character. But five practical questions can improve your odds of making sound judgments, even when the data is incomplete or unclear, opinions are divided, and the answers are far from obvious.

Where do these questions come from? Over many centuries and across many cultures, they have emerged as men and women with serious responsibilities and have struggled with difficult problems. They express the insights of the most penetrating minds and compassionate spirits of human history. I have relied on them for years, in teaching MBA candidates and counseling executives, and I believe that they can help you, your team, and your organization navigate the grayest of gray areas.

This article explains the five questions and illustrates them with a disguised case study involving a manager who must decide what to do about a persistently underperforming employee who has failed to respond to suggestions for improvement. He deserves a bad review, if not dismissal, but higher-ups at the company want to overlook his failings.

How should the manager approach this situation? Not by following her gut instinct. Not by simply falling into line. Instead, she needs to systematically work through the five questions: What are the net, net consequences of all my options? What are my core obligations? What will work in the world as it is? Who are we? What can I live with?

To grapple with these questions, you must rely on the best information and expertise available. But in the end you have to answer them for yourself. With gray-area decisions, you can never be certain you’ve made the right call. But if you follow this process, you’ll know that you worked on the problem in the right way—not just as a good manager but as a thoughtful human being.

Net, Net Consequences

Gray-area problems are rarely resolved in a flash of intuitive brilliance from one person; as a very successful CEO told me, “The lonely leader on Olympus is really a bad model.” So your job is to put aside your initial assumption about what you should do, gather a group of trusted advisers and experts, and ask yourself and them, “What could we do? And who will be hurt or helped, short-term and long-term, by each option?”

Don’t confuse this with cost-benefit analysis, or focus solely on what you can count or price. Of course, you should get the best data you can and apply the relevant frameworks. But gray-area problems require you to think more broadly, deeply, concretely, imaginatively, and objectively about the full impact of your choices. In the words of the ancient Chinese philosopher Mozi, “It is the business of the benevolent man to seek to promote what is beneficial to the world and to eliminate what is harmful.”

In today’s complex, fluid, interdependent world, none of us can predict the future with total accuracy. And it’s sometimes hard to think clearly about gray-area issues. What’s important is taking the time to open your mind, assemble the right team, and analyze your options through a humanist lens.

Core Obligations

Involves stepping out of your comfort zone, recognizing your biases and blind spots, and putting yourself in the shoes of all key stakeholders, especially the most vulnerable ones. How would you feel in their place? What would you be most concerned about or afraid of? How would you want to be treated? What would you see as fair? What rights would you believe you had? What would you consider to be hateful? You might speak directly to the people who will be affected by your decision, or ask a member of your team to role-play the outsider or victim as persuasively as he or she can.

You have serious obligations to everyone simply because you are a human being. When you face a gray-area decision, you have to think—long, hard, and personally—about which of these duties stands at the head of the line.

The World as It Is

The third question pushes you to look at your problem in a clear-eyed, pragmatic way—seeing the world not as you would like it to be but as it is. Ultimately you need a plan that will work—one that will move an individual, a team, a department, or an entire organization through a gray-area responsibly and successfully. Leaders rarely have unlimited freedom and resources, so they must often make painful choices. That is why, after considering consequences and duties, you need to think about practicalities: Of the possible solutions to your problem, which is most likely to work? Which is most resilient? And how resilient and flexible are you? To answer those questions, you need to map the force field of power around you: who wants what and how hard and successfully each person can fight for his aims.

Who Are We?

According to an old African adage, “I am because we are.” Put differently, our behavior and identities are shaped by the groups in which we work and live. As Aristotle said (and as a vast body of scientific literature has since confirmed), “Man is by nature a social animal.” So this question asks you to step back and think about your decision in terms of relationships, values, and norms. What really matters to your team, company, community, culture? How can you act in a way that reflects and expresses those belief systems? If they conflict, which should take precedence?

To answer those questions, you might think about the defining stories of a particular group—the decisions and incidents that everyone cites when explaining the ideals to which you are collectively committed, what you have struggled to achieve, and what outcomes you try hard to avoid. Of all the paths you might choose in this gray area, which would best express what your organization stands for?

This question comes fourth because you shouldn’t start with it. Unlike the first three, which require you to take an outsider’s perspective on your situation and consider it as objectively as possible, this one addresses you as an insider, at risk for adopting an insular, limited view when you consider norms and values, because we are naturally inclined to take care of our own. So counterbalance that tendency with the thinking prompted by the previous questions.

Living with Your Decision

Good judgment relies on two things: One is the best possible understanding and analysis of the situation. The other involves the values, ideals, vulnerabilities, and experiences of whoever will be making the decision. Ultimately you must choose, commit to, act on, and live with the consequences of your choice. So it must also reflect what you really care about as a manager and a human being. After considering outcomes, duties, practicalities, and values, you must decide what matters most and what matters less. This has always been the challenge of taking on any serious responsibilities at work and in life.

Leadership can be a heavy burden. It is also a compelling, crucial challenge. In gray areas, your job isn’t finding solutions; it’s creating them, relying on your judgment. As an executive I greatly respect once told me, “We really want someone or some rule to tell us what to do. But sometimes there isn’t one, and you have to decide what the most relevant rules or principles are in this particular case. You can’t escape that responsibility.”

Joseph L. Badaracco  – is the John Shad Professor of Business Ethics at Harvard Business School, where he has taught courses on leadership, strategy, corporate responsibility, and management.

The full version of the article appeared in the September 2016 issue (pp.104–107) of Harvard Business Review.



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