The training profession excels at order. After all, its function is to provide clear principles and tools for people to learn the skills they need to succeed in their jobs. Trainers explain best practices, list the steps to achieve them and lead practice exercises. This approach has succeeded since education was born, and it undoubtedly will continue.

It works well for learning skills and tools but less so in leadership development. While there are many trainable leadership skills and tools in such core leadership competencies as strategic thinking, political alignment, smart communication and talent motivation, they do not, by themselves, produce effective leadership.

Leadership requires something that lies outside of the orderly world of tools and skills. That something is wrestling with the messiness of the leadership life, where much is unknown and uncontrollable. Succeeding requires taking behavioral risks to create and implement ideas.

The Messiness of Leadership

Leadership is not like any other job. In fact, you can’t really call it a job. Leadership is a mindset with which leaders generate new ideas to lift their organization into the future and then convince others to go along with them. It’s a messy business, with the messiness coming from three primary places:


The fate of a new idea is untested and, hence, unknown. It could turn out to be great, mediocre or awful. To address an issue standing between a problematic status quo and future success, leaders have to travel into an uncomfortable, unknown territory with no signposts pointing toward the destination. To find it, leaders have to ask for directions.

Resistant Followers

The second cause of messiness appears when leaders nervously wind along a curvy road of idea-making and notice their followers dragging behind. They, too, are uncomfortable with uncertainty and resist in various ways: arguing against the initiative, disengaging or making for the door. They also might come to love the idea and want to support its development.

The Fears Inside the Leader’s Head

Pursuing new things with uncertain outcomes is scary, yet scariness provides leaders an important incentive to explore unknown situations and learn how to convert them to ideas that matter. To achieve that goal, however, they need a clear-eyed vision without filters clogging it with inaccurate or inadequate information.

All this messiness is … awkward. There is so much people can’t predict, much less understand or control. Rather than leaping into an exploration of possibilities with unscripted questions and activities, leaders often comfort themselves with defensive, counterproductive behaviors. Grabbing the checklist from the latest training will not rescue them and could throw them off course.

Developing leaders means delving into the disorderly, unkempt life of human behavior. Whether they are dealing with their teams, shareholders or customers, learning what those people want is critical to discovering what and how ideas will work. That understanding leads to uncomfortable conversations about previously unimagined opportunities; organizational dysfunction; and opinions on the progress, or lack thereof, in the idea-testing phase.

Leadership is not about finding one’s courage but, rather, accepting the fear that goes with the new, and then finding the courage to surface its possibilities.

Developing a Mindset that Embraces Behavioral Risks

How can leaders develop a mindset that embraces taking behavioral risks to pursue the possibilities for the future? Here are five ideas:

1. Understand the leadership role.

Management works with known, finite solutions to everyday problems. Leadership focuses on the infinite potential pathways to the future, without the safety valve of precedent. Leaders have to abandon routine to-do lists and move toward the disordered, uncharted space of idea-making.

For leaders, winning is not about knowing the answers but, rather, knowing how to search for them. Steering on the road of discovery may look inelegant, as the leader will stumble into blind alleys and wrong turns. However, projecting executive confidence arises from belief in the quest, not in knowing its destination before arriving there.

2. Explore the leader’s relationship with risk.

Accepting the scariness of risk is fundamental to leadership, as without taking chances, change does not happen. Brave words to the contrary, many leaders have an aversion to risk. Unconsciously, it signifies danger, being out of control or failure. Conversations, written exercises and other self-reflective work will build self-awareness. Questions might include:

  • What is their experience with taking risks?
  • What inner conversations do they hold when confronted with risk?
  • What are the possible consequences of taking risks?
  • How do they feel about the potential reactions of others?

3. Role-play real life problems.

Role-playing that mimics real-life situations offers an effective way to practice new behaviors. Asking participants to switch and play different roles increases insight and appreciation for why others act the way they do. Most importantly, it allows participants to experiment with new behavioral approaches. Maximize the experience with robust audience and role-player feedback.

4. Meet new audiences.

There is nothing like a speech to test whether someone has done his or her homework on what ideas appeal to others. Rather than safe groups whom leaders know, choose unfamiliar groups outside or within the company. Reaching out to members of the target audience ahead of time can take leaders out of their comfort zones, particularly when they could learn that their pet ideas don’t match the reality of others. Asking unplanned follow-on questions and modifying concepts accordingly can be nerve-wracking but is how successful ideas emerge.

5. Deliver frank feedback.

Feedback is critical to professional growth. The more specific the feedback, the better. A 360-review offers a powerful, individualized assessment. While hearing private perceptions held by others can be jarring, this feedback provides leaders with invaluable information on how their behavior lands with others and about its consequences. It also builds a roadmap of what they have to learn about their constituents.

Many “type-A” captains of industry stroll confidently into leadership development programs, making loud comments, vigorously shaking hands and slamming laptops onto tables. Then, the stack of 360 test results appears at the front of the room, and a thick, anxious hush descends. There is nothing like having to read the opinions of others to put a dent in one’s carefully tended self-view. The bravado shifts to comprehensive self-reflection and hard, important work.

The reward of taking behavioral risks is to discover what the future might hold – and how to get there with the help of others.