Cultivating Fearless

I recently read an article based on the newly released book, The Corner Office, in which New York Times columnist Adam Bryant shares the themes that emerged from his interviews with more than 70 chief executives and other leaders. He synthesized his findings down to five traits that CEOs look for in leaders:

• Passionate curiosity
• Battle-hardened confidence
• Team smarts
• A simple mind-set
• Fearlessness

While I found the list interesting, I was most drawn to the last trait – fearlessness. The article presented fearlessness as a somewhat rare character trait embodied by a few emboldened leaders who dared to challenge the status quo. What baffles me is if CEOs value fearlessness so highly, why don’t organizations put more emphasis on cultivating this quality to be part of the culture? It often seems organizations do exactly the opposite.

The cost of valuing compliance and sameness over diversity of thought and risk taking comes clearly into focus when the stakes are highest. During the height of the recession I watched some organizations get creative and take risks to better position themselves to emerge in stronger positions, while others retracted into fearful places, cutting everything in site without giving much thought to longer term implications, and resorting to intimidation to get compliance. That’s the difference between fearless and fearful leadership.

Organizations can cultivate a culture of fearlessness by:

1. Providing leaders with varied experiences early in their careers. Leaders who have the opportunity to work in a variety of situations early in their careers develop perspective and flexibility as they adapt to new circumstances and challenges. This helps leaders to trust themselves more deeply. A quiet, well-founded self-confidence is essential in a fearless leader. (I am not talking bravado, which is actually just fear externalized – think scared dog with teeth bared.) The most recalcitrant leaders I’ve met are those who were not asked to step outside their comfort zones until very late in their careers.

2. Valuing insightful risk taking. I’ve seen organizations where the proverbial “career-ending move” can be as small as making too blunt a statement in a public forum. These organizations value compliance, sameness, and predictability – and that’s what they get: leaders who value “niceness” over candor, and collusion over real change. These leaders tend to panic when the intensity of change means they can no longer hide behind their carefully crafted facades of leadership. Organizations that value risk-taking encourage independent critical thinking, use failure as an opportunity to learn, and ensure that appropriate risk taking is rewarded.

3. Encouraging edgier questions. The questions people are willing to ask and answer determine the extent to which change is possible. If challenging assumptions is considered a punishable offense then don’t expect too much of it. Yet the assumptions underlying our business models are changing at ever increasing rates. Asking game changing questions should be an expectation of leadership rather than an act of courage. Real change begins with the willingness to question assumptions and engage in honest dialogue about what else is possible.

4. Establishing a higher purpose that is worth taking a risk for. Leaders take risks to accomplish something worthwhile. If you think about it, most leaders who cower or hide have no higher purpose than saving their own skins. The higher and more meaningful the purpose, the more likely people are to take a risk to achieve it. Making money in and of itself does not qualify as a higher purpose in my book. If the money is not made in service of a greater contribution then it may serve solely as a motivator to cheat, which is risk taking of sorts, but not the kind that serves a shared greater good.

When it comes to fearlessness you reap what you sow. Organizations that cultivate fearless leaders plant the seeds early by giving young leaders varied experiences, support appropriate risk taking throughout the leaders’ careers, and harvest the rewards with insightful risk taking in tough times.

If your leaders aren’t fearless, don’t blame the leaders – look to the system that grew them.

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