Seven Leadership Mistakes That Wear Away at Your Company’s Will to Win

For any team, the only acceptable result should be winning. But all too often, things don’t go as planned—and when first this project and then that project veer off course, teams start showing signs of a disease that can kill execution. John Hamm describes how the disease of “failing elegantly” can infect your organization and how to cure it.

No one wants to lose. That’s true whether you’re talking about the Super Bowl, a friendly basketball game with the neighbors, or a footrace between eight-year-olds. Yes, the desire to win is embedded in the human psyche. So why is it that in the business world the “win or (almost) die trying” principle seems to falter? Why do so many talented, well-led teams, enterprises, and organizations—many of them with clear, reasonable goals—fail to win victories that should have been easily within their grasps?

Leadership expert John Hamm says it’s because they’ve been infected with a disease he calls “failing elegantly.”

“Failing elegantly is a very sophisticated and veiled set of coping behaviors by individuals, the purpose of which is to avoid the oncoming train of embarrassment when the cover comes off the lousy results that we’d prefer no one ever see,” explains Hamm, author of Unusually Excellent: The Necessary Nine Skills Required for the Practice of Great Leadership. “In other words, it’s a fancy way to lose.”

Essentially, says Hamm, this debilitating syndrome sets in when people stop believing they can be successful and start devoting their energy to how best to lose.

“There is no obvious moment when the danger of failure comes riding in on a pale horse,” he notes. “But there is that moment, and everyone can feel it, when a project or the commitment to the promised results enters the risk zone—when challenges arise and there are no clear answers or remedies. It is precisely at this fork in the road—when egos and reputations get shaky—that leaders must recognize the signs of an impending crisis of confidence and intervene with specific messages and actions aimed at getting everyone back into the winner’s mindset.”

According to Hamm, the driving elements of failing elegantly are 1) having a sophisticated explanation for the loss, and 2) making sure we appear to have tried everything in our power to avoid this unwanted outcome. But, he notes, what this mentality forgets is the following harsh reality: There are no style points for second place.

Hamm has spent his career studying the practitioners of unusually excellent leadership via his work as a CEO, venture capitalist, board member, high-level consultant, and professor of leadership at the Leavey School of Business at Santa Clara University. In his powerful back-to-basics reference book, he offers both seasoned and aspiring leaders a framework for understanding and a guide for applying the battle-tested fundamentals of leadership at every stage of their careers.

Read on for a few leadership mistakes that put your team in danger of failing elegantly—along with some remedies to get them back into the winner’s mindset.

Setting impossible goals. Leading the goal-setting process to arrive at objectives that are perfectly sized is very tricky work, but this effort has never been more important to success than it is in today’s geographically dispersed, virtual organizations. Taskmasters and pacesetting leaders need to learn the fine line between an invigorating challenge and a wholly deflating expectation. They also need to realize that everyone on the team may not share their level of maniacal commitment.

“While top performers are inspired by ‘stretch’ goals that seem slightly out of their reach, smart team members will not waste their time training for a ‘three-minute mile,’” says Hamm. “Goals that are clearly beyond any reasonable confidence of achievement are worse than easy goals—they actually disengage your team’s energy. The predictable and natural response is ‘Why bother?’”

Letting people get pseudo-wins by “majoring in the minors.” Very talented people can and do lose focus on the critical path problems that must be solved to transform an idea into reality. Those are often the knottiest problems, and sometimes we resist them for a period of time, preferring to create some satisfying momentum on simpler tasks, or ones that are simply more fun.

“Leaders must develop an eye and ear for this weakness—and must try to listen for it in every conversation and look for it in every ops review,” notes Hamm. “

Tolerating “The dog ate my homework” and other common excuses. In an organization, too much tolerance can be a dangerous notion, mainly because without a clear line in the sand defining acceptable and unacceptable, a blurred line between success and failure follows. When you’re failing elegantly, for example, you tolerate “The dog ate my homework” and other classic excuses. No results plus a good excuse is presented in lieu of results—and tolerated. Massive amounts of energy are poured into sophisticated justifications and rationalizations for certain courses of action, and there is veiled blame for everything outside the team’s control.

“What you want, and what the winner’s mindset demands, are insightful explanations for the gap between expected and actual performance,” says Hamm. “These are informed guesses—as informed and objective as they can be, untainted by the effort expended in dodging responsibility. There is tolerance of the simple fact that we don’t have control over every variable in the game, so at times—through either forces outside our influence or simply not having run our best play—the results are not as we wish.”

Allowing sloppiness and imprecision. The nice guy in you wants to avoid the perception of being a hardcore hard-ass and will politely look the other way, or catalog it away with some good-natured humor, allowing a corner to be cut, a report to be incomplete, or some shoddy work to pass as acceptable. Shoddy work and sloppiness almost always stem from being lazy or uncommitted or not having enough pride in the finished work.

“Leaders want to be good people, and they want to show others that they have the wisdom to accept human frailty,” notes Hamm. “So they allow themselves to tolerate a little sloppiness here and a little imprecision there in their subordinates’ work. But high reliability organizations never allow sloppiness, because they know it equals death. Unusually excellent leaders have a zero tolerance policy for sloppiness.”

Encouraging “editorialized” data. One of the most pernicious points where failure can take hold is in the feedback process. Leaders, being eternal optimists and enthusiasts, also have a dangerous tendency to signal, often unconsciously, their dislike of bad news, their inner revulsion toward failure. When that happens—especially when that leader hasn’t regularly established an absolute demand for accurate, objective data—subordinates will begin to shape and color the data to meet the leader’s hopeful expectations and emotional needs, rather than the leader’s intellectual needs. The feedback data starts becoming corrupted, and that in turn begins to undermine the overall strategy—until the likelihood of success itself begins to plummet.

“Unusually excellent leaders demand that performance feedback data be delivered promptly and be uncolored, objective, plentiful, and robust,” says Hamm. Failing to measure what matters. The right metrics will serve you in enormously useful ways. As the Crosby Quality Institute reminds us: You will get what you inspect, not what you expect.

Hamm writes about one CEO who was constantly entertaining requests from his sales force for changes to the company’s product line—change orders—in response to “customer requests.” In this case very few of these requested changes, which came at great expense in engineering time and cost, resulted in orders from the people who had passionately argued the case. Instead of getting upset about it, the CEO simply asked that the team begin to track the percentage of change orders resulting in sales orders, and—what do you know?—this costly practice came to a screeching halt as soon as the sales force knew their bosses were looking at this data, by salesperson, every month.

“Measuring what matters is perhaps the very highest use of leadership authority in leading the domain of execution,” explains Hamm. “Once the plan is set, the resources and funding are committed, and the action starts, there is mostly just feedback and response to the unknowns of the battle to be managed. The one thing you must have, to make the real-time course corrections that will inevitably be required, is good data. Invest in the design and the machinery required to gather, analyze, and present the data you need—quickly, accurately, and easily. This, more than anything else, will serve your leadership needs in the arena of live ammo—where the score is kept, the winners get to keep playing, and the losers go home.”

Allowing an absolute commitment to winning to slip. A tolerance for excuses, corrupt data that compromises strategy, and a distorted view of what is really happening “out there” is akin to boiling a frog one degree at a time. The frog can’t tell how hot the water has gotten until it is dead. But if you put all these factors together and add the heightened sense of urgency that always characterizes the execution phase, you’ll have plenty of the necessary ingredients in place for systematic failure. The key factor is the resignation and rationalization that occurs when we conclude that winning seems out of reach.

“These are dark moments for any team,” says Hamm. “And yet, we all know that we should leave it all on the field and, as the saying goes, ‘win or die trying.’ But when you’ve already begun to distance yourself from your absolute commitment to winning, you start blaming everything and everyone—your teammates, the strategy, bad luck, crooked competitors, insufficient support, and, most of all, the man or woman in charge. The fact that many people—the honest and secure ones first—see what’s happening and hold the behavior in contempt often proves to be an effective vaccine against the contagion spreading.”

“Passive acceptance of failure, and the rationalization that always goes with it, is a cancer that can begin anywhere in the organization, then metastasize to every office, including your own,” says Hamm. “You can prevent it by setting clear and precise standards of behavior for everyone on the team, as well as clear consequences for the violation of those standards. And you can control it through continuous and open communication with every member of your team.”

John Hamm is one of the top leadership experts in Silicon Valley. He was named one of the country’s Top 100 venture capitalists in 2009 by AlwaysOn and has led investments in many successful high-growth companies as a partner at several Bay Area VC firms. Hamm has also been a CEO, a board member at over thirty companies, and a CEO adviser and executive coach to senior leaders at companies such as Documentum, Cisco, Hewlett-Packard, TaylorMade-adidas Golf and McAfee. John teaches leadership at the Leavey School of Business at Santa Clara University.