The first question of Leadership: Why do I choose to lead?

Excerpt from The Book of Beautiful Questions  (Just Released) by Warren Berger 

The first question of Leadership: Why do I choose to lead?

Aspiring leaders often don’t spend enough time considering whether there is a greater purpose driving their leadership aspirations—or clarifying what that purpose might be. The demands of leadership now are so great that unless one is driven by a sense of purpose that transcends personal ambition—and unless one enjoys the actual day-to-day work of engaging with and leading others—the pursuit may not prove satisfying or sustainable in the long run.

If many of those chasing leadership positions are driven by personal ambition alone, we can blame that, at least in part, on our educational system, observes Susan Cain, author of Quiet. In a recent essay, Cain noted that universities, and the students entering them, have become extremely focused on leadership. (The schools want to be seen as institutions that produce leaders, while the students all want to become leaders.) But as Cain points out, both sides seem to be defining leadership in shallow terms—based on how many achievements a student can list or the number of clubs that student has become president of. This creates the sense that the overall objective is “to be a leader for the sake of being in charge, rather than in the name of a cause or idea [the student cares] about deeply.”

Noting that the world needs leaders who are called to service rather than to status, Cain offered up a beautiful question: What if we said to our would-be leaders, ‘Take this role only if you care desperately about the issue at hand’?

To reframe Cain’s challenge as a “self-question,” anyone considering a leadership role in any organization might want to first ask,

Why do I want to lead this endeavor or these people—and why would they want me to lead them?

If you have a worthwhile answer for the first half of the question, it may apply to the second half as well. For example, the school principal Nadia Lopez, of the renowned Mott Hall Bridges Academy in Brooklyn, New York, believes that as a leader of that school she is pursuing a goal much larger than her own personal ambitions. “I tell my teachers that we are chosen to be here, because we’re supposed to transform a community that doesn’t believe in themselves,” Lopez says.

That makes clear why she would want to lead this particular school—and why the students and teachers would want her to lead them (who wouldn’t want a leader with that kind of conviction?). On the other hand, if Lopez’s answer to the first part of the question was more along the lines of, I feel I’m entitled after all these years to be the principal of this school or I need the pay raise, that would be a poor answer to the second part of the question.

Before considering why you’d want to lead a particular organization, there’s a question that’s even more basic, and can be applied more generally: Why do I choose to lead? (referring to not just this organization, but any organization or endeavor). The question is designed to force aspiring leaders to really think about what’s driving them to pursue a leadership challenge. The former Campbell’s chief executive Doug Conant recommends breaking down the question into a number of others including:

How do you want to leverage your special gifts and interests to make the world a better place?

The key is to make sure the reasons why you want to lead—perhaps based on your interests, passions, strengths—are aligned with the challenges and everyday realities of being a leader in today’s world. Wanting to lead is one thing; being ready or able to do so is quite another.

Given that it’s hard to be a good and effective leader unless you’re committed to helping people, aspiring leaders should inquire about their own willingness to do that. Those with a natural interest in helping others to reach their potential are well-suited to lead in today’s environment. Those more focused on their own achievements and goals may be less so.

Indeed, this speaks to what may be the greatest adjustment for high achievers attempting to transition to a leadership role. As Conant puts it, “When you become a leader, it’s not about ‘you’ anymore.” Angie Morgan of the consulting firm Lead Star says that many of the executives she coaches were promoted to leadership roles because they excelled at various task-driven, results-oriented jobs within their organizations—which made them rising “stars.”

But upon assuming a leadership role, Morgan says, they have had to shift their entire focus and approach. “They were used to being ‘doers,’ but now they are expected to focus more on building relationships.” That often involves more delegation of the work people may love doing, more sharing of responsibility, and a willingness to let others shine as the top performers and producers.

Some overachievers have trouble making that transition. Research by the Hay Group focused on overachievers who become leaders and found they “tend to command and coerce rather than coach and collaborate, thus stifling subordinates,” and “may be oblivious to the concerns of others.”

With that in mind, aspiring leaders should ask themselves whether they’re truly ready to shift from performing to leading. Rather than thinking of leadership as the ultimate starring role in an organization, the question to ask is:

Am I willing to step back from individual achievement—in order to help others move forward?

The notion that a leader’s first and foremost job is to help others succeed is not entirely new. But it has gained much wider acceptance with the growing “servant leadership” movement. In terms of an overall goal, the “servant leader” is advised to try to do several things: help people within the organization to succeed at their jobs; prepare them to become leaders themselves; and simultaneously try to find ways to serve a larger community, beyond the organization.

Morgan, who served as an officer in the Marine Corps before cofounding the Lead Star consultancy, points out that service-based leadership has its roots in the military—where leaders are expected to prepare others to become leaders themselves (on the rationale that the current leader could be lost in battle at any time, and others must be prepared to step forward). Morgan says that military leaders also learn, in the field, that the unit depends—sometimes in life-or-death terms—on each person being capable of succeeding in their role. This incentivizes leaders to do the work necessary to help everyone in the unit improve their skills.

But bringing this kind of service-oriented, relationships-based leadership approach into the business world isn’t easy, Morgan and others concede. The notion of a leader as an on the ground “helper” runs counter to the more remote, “command and control” approach favored by many high-powered officials and executives. It requires close contact. It calls for “softer” skills, such as listening, effective communication, and coaching. And it demands another quality that appears to be in short supply in many leadership circles—humility.

Warren Berger


Warren Berger has studied hundreds of the world’s leading innovators, entrepreneurs and creative thinkers to learn how they ask questions, generate original ideas, and solve problems. His writing and research on questioning and innovation have appeared in Fast Company, Harvard Business Review and Wired.   His website is   His new book (Just Released) is “The Book of Beautiful Questions.” 


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