The Risky Business of Leadership Development

Business success today demands careful attention to risk management. Contingency plans, redundant systems, business continuity insurance, and countless other vehicles protect organizations from the volatility and unpredictability of today’s business landscape.

But there’s one area where risk should actually be cultivated rather than averted, and it’s the on-the-job growth, learning, and development of leaders.

By definition, developing a leadership capability, skill, or experience set means throwing someone into the unknown to do what he or she has not mastered or perhaps even attempted before. There are no guarantees of success when a leader is given an opportunity to develop on the job. But, it’s precisely through these sorts of challenges that humans in general—and leaders in particular—learn most quickly and powerfully.

My ongoing research with senior leaders in 25+ organizations across the U.S. paints a compelling yet simple picture of the most effective leadership development strategy. When asked how their own managers or mentors helped them to grow the most, the number one response from executives is some permutation of “they took a risk on me,” with more than 90% of those polled citing this as a pivotal development experience.

These executives talk about being thrown in “beyond their depth,” left to “figure it out themselves,” and forced to “sink or swim.” Many of these stories have happy endings, with the leader emerging from this trial by fire successful and triumphant. More often, the stories involve mistakes, setbacks, and even high-profile failure. Yet, these more challenging endings invariably launch additional stories of trust, hard conversations, candid feedback, and support.

The executives who navigated their risky development assignments successfully learned a lot; those who encountered challenges likely learned more. And in both cases, their managers or mentors took a risk.

“Sure bets” and “stretch” simply don’t go hand-in-hand. So, if it’s a “stretch” that’s required to build genuine leadership capacity, how can an organization develop its bench without putting the entire enterprise at risk? Effective developers of leaders demonstrate some best practices that strike the balance. They:

  • Calculate the risks. The most effective developers have the capacity to judge a prospective leader’s capacity. They weigh past results, efforts, and challenges and can assess the readiness of the person for a new task. At the same time, they understand the organizational landscape sufficiently to evaluate the real costs associated with outcomes that might fall short of success.
  • Give others enough rope. Effective developers don’t give others so much rope that they’ll hang themselves. Instead, they give just enough so that developing leaders can go out, explore, experiment, struggle if appropriate, and still be reigned in safely if necessary.
  • Consider their own political capital. Since even calculated risks are still risky, effective developers know how much cover they can provide—and how much flack they can absorb—if the learning experience turns out to yield less than desirable business results.
  • Make peace with mistakes. The most profound developers of leaders have developed a visceral understanding that errors, miscalculations, and failure fuel learning. They have cultivated a big picture perspective and appreciate that sometimes short-term sacrifices are necessary to build the long-term leadership capacity required for the enterprise’s sustenance and success.

Developing leaders is not for wimps. Done properly, learning can be messy. Development can be dicey. But it’s precisely through the act of taking risks on others that today’s leaders build tomorrow’s leaders—people who’ll be prepared and capable of carrying on the important work of the enterprise. And imagine the risk associated with not doing that.

People who don’t take risks generally make about two big mistakes a year. People who do take risks generally make about two big mistakes a year.

— Peter Drucker


Julie Winkle Giulioni
Julie Winkle Giulioni
Julie Winkle Giulioni is a guardian of growth, defender of development, and promoter of potential in today’s workplace. She’s the author of  Promotions Are So Yesterday: Redefine Career Development. Help Employees Thrive and co-author of the international bestseller, Help Them Grow or Watch Them Go: Career Conversations Organizations Need and Employees Want. Named one of Inc. Magazine’s Top 100 speakers, Julie offers memorable and actionable live and virtual keynotes and presentations worldwide. Julie is a regular columnist for Training Industry Magazine, SmartBrief, and contributes her thought leadership around career development and workplace trends to The Economist and other publications. You can keep up with Julie through her blogLinkedIn and Twitter.

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  1. A leader has to make decisions. Often the act of choosing requires a certain amount of risk: we live in an era of unpredictability and we do not know what results our decisions will lead to. Taking risks can be uncomfortable, because it makes us feel uncomfortable, it forces us to give up control, it takes us away from our certainties. At the same time, however, taking risks encourages us to trust in a positive result and to have faith in our path of personal growth, however things go. For a leader (or would-be leader), taking risks is a necessary evil. It is critical to successful leadership and can help develop entrepreneurial skills by teaching valuable skills one would never have learned otherwise. It also helps lay the foundation for the wisdom and confidence that a true leader needs to grow.

    • I really agree, Aldo. And I wonder about the expression ‘necessary evil’. Is it time to think about it simply being necessary and central to leadership? The positive benefits of smart risk taking (which you outline eloquently) are irrefutable. And given the dynamic and unpredictable environment within which we operate, not taking risks feels like the greater ‘evil’ these days. Thanks so much for your comment… I really appreciate it.