9 Virtues Blog

Some Thoughts on Optimism

by Rob Jenkins

12/10/2016

In a recent leadership development session with a group of executives from a large Midwestern corporation, we got to talking about optimism. I was covering the chapter in The 9 Virtues on “Hope,” of which optimism (we contend) is one aspect, and the discussion was about the difference—or rather the fine line—between being optimistic and wearing rose-colored glasses. We also debated the opposite of optimism: Is it pessimism, or is it actually cynicism?

In this post, then, I’d like to share some of my thoughts about optimism as a function of leadership, taken both from the book and from that discussion.

My first thought is that optimism can’t be faked, or at least not for very long. It’s more than just acting upbeat, saying appropriately positive things, or wearing a smile plastered to your face. Genuine optimists have a consistent way of speaking and of approaching challenges that resonates with people because it arises from deep within them. They truly believe things are going to turn out for the best and see opportunities where other people see difficulties.

Such genuine optimism can be a powerful tool for leaders—as long as it is tied to reality. Few things are as motivating as a belief that everything really is going to work out for the best. But if that belief proves to be false too many times, perhaps because the situation really was direr than anyone let on, then people will, over time, become jaded and cynical. So the optimistic leader has to be a realist, too, or else people will just stop believing—and stop being motivated.

In this sense, optimism is closely related to what my high school basketball coach used to call “quiet confidence.” Because we had a pretty good team—big, fast, and skilled—it would have been easy for us to think we were going to win for those reasons alone. But our coach preached to us constantly that the difference between confidence and “cockiness” is that the cocky team believes it’s going to win just by showing up (and too often gets beat as a result), whereas the quietly confident team believe that, if they play their hardest and execute the way they’ve been coached, they will win the game.

Another term for this, as it applies to leadership, might be pragmatism. We sometimes see optimism and pessimism as two ends of the spectrum with pragmatism somewhere in the middle. But that’s not really what pragmatism is. It’s actually a form of optimism—but optimism tempered by Wisdom. (As a side note here, we were frequently amazed, as we wrote the book, at how interrelated all the nine virtues are. It was impossible to write about one virtue without several others cropping up.)

In other words, pragmatists are actually optimists rooted in reality. They have the kind of quiet confidence that’s infectious, believing deeply that if they and the people around them work hard and do the right things, then in the long run the organization and all of them individually will prosper. At the same time, pragmatists don't ignore the reality of the situation on the ground and the challenges it presents. They just believe that, with the right approach and a little teamwork, those challenges can usually be overcome.

When optimism is divorced from reality, it can quickly become pie-in-the-sky fantasy. That is NOT motivating. In fact, people will not long follow a leader who refuses to acknowledge reality or deal with its challenges. I once worked for a CEO who had a reputation as a visionary, and she was—at first. Indeed, many of us in the organization were inspired by her vision, and together we took the organization to new heights. Over time, though, as successes piled up and (more to the point) that leader began to believe her own press, she concluded that she could not possibly do any wrong, and that if she could dream it, she could achieve it.

That turned out not to be the case. As her dreams for the organization expanded, they eventually entered the realm of the unattainable—fantasy-land, to be blunt. Many of us saw where she was headed, the train-wreck around the corner, but she couldn’t be swayed from taking us down that track. Anyone who attempted to inject a dose of reality into the discussion was quickly labeled a “nay-sayer” or a cynic. And so of course the train-wreck occurred, in slow-motion, as we all watched. (This story also highlights the importance of Humility—a willingness to listen to others—as an element of vision. So rather than saying that pragmatism is optimism tempered by Wisdom, perhaps we should say it is optimism tempered by both Wisdom and Humility.)

Which brings me to another point: the role of the cynic. When the leader’s vision is not rooted in reality, over time nearly everyone becomes cynical, and understandably so. But even when things are going well, and the leader takes an appropriately pragmatic approach, there is going to be at least one cynic in every organization.

I’ve always believed that the cynic plays an important role. It’s the cynic—who may just be a pragmatist with poor people skills—that tends to keep us centered, to point out the flaws in our reasoning and warn us of the coming train wrecks. Of course, the problem with cynics is that they tend to see a wreck around every bend of the track, and the vast majority of those collisions never take place. It their own way, cynics are just as unrealistic as fantasy-mongers—except when they’re not.

That’s why a certain amount of cynicism should be encouraged in an organization. At the very least, people should feel free to speak out about potential problems they see with ideas, including the leader’s pet ideas, without being labeled as negative or “nay-sayers.” That sort of Honesty (another of the Virtues!), combined with Humility, can help keep leaders focused and rooted in reality.

We just can’t have too many cynics. One cynic can sound a much-needed warning bell; an entire organization of cynics would never set out to begin with for fear of coming catastrophes. Constant cynicism is ultimately no different from negativism. There might not be any way to keep a confirmed cynic from being cynical, and that’s fine; but the way to keep the rest of the people in the organization from becoming closet cynics is to lead with just the right degree of pragmatic optimism.

Moreover, even if it’s good to have a cynic or two around, leaders themselves cannot be that person. Imagine if the person charged with providing vision for the entire organization were to be constantly perceived as cynical and negative. How much confidence are people ultimately going to have in the organization? In that individual personally?

In the end, effective leaders need to cultivate and model a reality-based optimism that acknowledges challenges and problems—I hate it when people refer to every problem as a “challenge”; sometimes they’re genuine problems, darn it—without allowing people to be defeated by those challenges and problems before they’ve even begun. Leaders can have a “can-do” spirit while still understanding that, in reality, there are probably some things the organization actually can’t do.

The best leaders, though, know what people are truly capable of—and know that, very often, they’re capable of a lot more than they think. Getting them to see that, and to perform accordingly, is the true genius of leadership. And it all stems from a healthy optimism.