Risking: The Heart of Daring Leadership

by Eileen Rogers

Vulnerability is not a concept I learned in business school. Nor, for that matter, theories about soft skills such as self-awareness, risk, emotional IQ, shame or courageous leadership. Yet, for today’s leaders to be relevant, effective and impactful, these ideas must become part of our everyday vocabulary and being.

“Command and control,” “armored leadership” and/or fear and shame-based management styles are concepts that don’t resonate well with the workforce we’re hiring today. We need braver and more daring leaders who will remove barriers to good work and healthy workplaces.

Dare to Lead by Brené Brown, Ph.D., LMSW, presents her latest research on leadership. Dr. Brown’s most important discovery is that courage is actually a collection of four skill sets that are teachable and observable. She also found significant barriers to courageous leadership. The biggest, with no close second, was the habit of avoiding tough conversations. We are simply not giving our teams the tough and productive feedback they need to be accountable and successful. Often, we choose shame and blame as our tools to avoid the vulnerability and risk in these conversations.

Other barriers uncovered in the research include:

  • Instead of proactively addressing people’s fears and feelings, we spend an unreasonable amount of time managing problematic behaviors.
  • Perfectionism and fear keep people from learning and growing.
  • Lack of connection and empathy causes diminished trust with our team members.
  • Not enough people are taking smart risks and being bold enough to meet the need for innovation.
  • We get stuck and defined by setbacks, disappointments and failures.
  • Too much shame and blame — not enough accountability and learning.
  • People are opting out of vital conversations about inclusivity and diversity for fear of looking wrong, saying something wrong or being wrong.
  • Organizational values are aspirational, instead of actual behaviors that can be identified, taught and evaluated.

Courage is one of my core values and a word our culture uses often. Dr. Brown’s research found it was very difficult for people to describe exactly what courageous leadership looks like. Many people simply believe that courage was something a person either did or did not have.

So, she asked the question in a different way: “What happens in the absence of courageous leadership? If we aren’t having direct, honest and tough conversations with people, what are we doing?” The answer, in most cases, was that “we are talking about them, not to them.” Often, the excuse given for this avoidance behavior was “we have a polite culture!” (Just a glance at our current political discourse clearly suggests otherwise.)

The four teachable “Skill Sets of Courage” that emerged from the data are:

Rumbling with Vulnerability — our ability to have tough and important conversations.

Living into Our Values — who we are is how we lead; leadership style is simply one’s core values translated into action every day.

Braving Trust — most of us believe we are trustworthy yet trust only a handful of others.

Learning to Rise — building our resilience to disappointments and failures.

As I reflect on my career a business owner (my “insight from hindsight”), I see how I once stumbled my way through these skills. My leadership lessons often came the hard way as “on the job training.”

Engaging in a few tough, direct and vulnerable conversations with two team members back in the 1990s would have saved me from an emotionally difficult and expensive lawsuit. At first, it seemed safer and easier to bury my head in the sand. By dealing only with surface issues, I avoided the heart of the situation (known as the “messy middle”). Dr. Brown’s definition of vulnerability is risk, uncertainty and emotional exposure. All three were elements of this key leadership lesson for me.

In business school, I remember learning about the inverse relationship of risk and return. Risk was mostly external and defined only in terms of money and finance. This column is a conversation about ongoing, healthy and internal risk, and daring to lead by taking off our armor and showing up instead with courage, compassion and connection. As Joseph Campbell expresses it, “The cave you fear to enter holds the treasure you seek.” Over the next few months, we’ll explore more about these concepts and skills.


After 40 years as president of her print and marketing company, Eileen Rogers’ encore career is now as a leadership coach and business advisor through her company One Creative View. She is a seasoned and accomplished entrepreneur and recognized community leader who is fiercely passionate about supporting and growing more vulnerable and courageous leaders. She is a certified Dare to Lead™ facilitator, Integrative Enneagram practitioner and executive coach.

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