Photo: Stuart Cahill

Joseph L. Badaracco is the John Shad Professor of Business Ethics at Harvard Business School and the author of numerous books on leadership, decision-making and responsibility. In an interview with Tom Fox, Badaracco discussed some of the central themes of his most recent book, “Managing in the Gray: Five Timeless Questions for Resolving Your Toughest Problems at Work.” Fox is a guest writer for On Leadership and the vice president for leadership and innovation at the nonprofit, nonpartisan Partnership for Public ServJoice. The conversation has been edited for length and clarity.

You write in your latest book that part of an executive’s job is to make tough calls and resolve grey area problems, situations where the analysis, facts and data fail to provide a clear answer. You suggest asking five basic questions to help make those hard decisions. What are those five questions?

The first is what are the net consequences? That is, if you have to make a decision that has a lot of uncertainty and significant human stakes, make sure you look at all your options, not just some of them, and consider the consequences for everyone who is going to be affected. A second question is, what are my core obligations? Consequences are really important, but so are core human obligations, and there are some things that are just wrong and you can’t do them. The third is what will work in the world as it is? Which means a world that’s uncertain, turbulent and surprising. The fourth one is asking, who are we? Most organizations have a set of core values that we really care about, how we treat people or how we treat each other. So you’ve got to test your options against that. Once you’ve asked these first four questions, you got to make a decision. That’s when you ask the final question, what can I live with?

You suggest asking what will work in the world as is, which certainly has implications for federal leaders operating in a highly politicized environment?

The one thing I would say about politics and this goes back to Machiavelli is that it’s easy to hear somebody say things about the world as it is, be politically astute and be cautious. You ought to be cautious. You don’t want to walk across a minefield. But Machiavelli also said that fortune favored the bold and the people he praised in his book, “The Prince,” who were running Italian city states, were often constrained in many ways. He said the best of them were thinking creatively and imaginatively about options. He was not mandating recklessness, but a combination of prudence and boldness. Can we find other ways to do things? Can we be broken field runners across this hazardous territory? That’s the real spirit of Machiavelli, and I think that’s sound general advice. Most people say I have three options, and they are pretty lousy. I think there’s often a fourth or a fifth. Sometimes there isn’t and you have to pick one of the three lousy ones. But look for those others. That’s true in the public and private sectors.

Can you give me your favorite example of a tough choice made by a historical figure and how that might apply to the world today?

When Abraham Lincoln was running for president, a big issue in the country was slavery. This was a tricky proposition for Lincoln because if he took the abolitionist position and said no slavery, it would cost him votes in some border states. And if he supported slavery, it would have cost him heavily in some of the northern states. So Lincoln came up with this brilliant political formula. He said he opposed slavery in the Northwest Territories. But he didn’t say he opposed it because it was morally wrong, but because it meant that free white men couldn’t move there with their families and prosper if they had to compete against plantation agriculture. He said these Northwest Territories should be splendid places for free white men. So he took what could have been a moral argument that might have left him just being an unknown Illinois legislator and replaced it with an economic argument that was creative and had enough political appeal to help him get elected. You can be critical of him or praise his creativity, but I think he was trying to be accountable to a number of important agendas. And that’s sort of how he zig-zagged, and what most historians would now say was relatively the right direction, because it gave us the Emancipation Proclamation and ultimately the end of slavery, and kept the country together because he was president.

What are the most important attributes of an effective executive?

One is the combination of persistence and flexibility. Knowing what you want to accomplish in the medium and longer run, but willing to be skilled and adaptive in pursuing your goals. If I had to single out one thing, it would be the quality of the work you do with other people day in and day out. It’s about building relationships of candor and trust. Your meetings need to be safe spaces where you work the problem while avoiding politics and personalities. People will believe that they are on the team and that their work and their views matter and they’ll give you the extra 10 to 25 percent. When you’re figuring out what you want to do and how to get there, you will have a lot better foundation to build on because you’ve worked the problem with other people. It’s making teams work and the relationship of trust and candor that you’ve got to try to foster.