The Behaviorist: Fearless leadership is full of fear

Kedren Crosby, president of Work Wisdom LLC - (Photo / Submitted)

Over the past few years, I have been observing a notable style of leadership that is fueled by the team, the collective good, the community. This new leader is particularly courageous. They challenge the status quo and are positive deviants in their fields. I call this bold approach to shepherding companies, communities, consumers and organizations “fearless leadership.”

Fearless leaders are emboldened by working toward justice for many rather than for themselves. Whether the leader is embedding socially responsible business practices, adopting increasingly equitable hiring norms or taking their company into new strategic territory, fearless leadership necessitates new levels of self-awareness and assertiveness. They are authentic in how they communicate and contagious in their use of positive behavior.

All of the fearless leaders with whom I have worked are comfortable discerning their purpose on the planet, reframing their crucible moments as strengthening opportunities and identifying the power source of their sustainable courage.

Fearless leaders tie every action directly to their meaningful work. They are intellectually humble and open to innovation, agility, failing fast and honoring ideas that come from any level in the organization. The urgency and passion of the fearless leaders are baked into the organizational culture.

I interviewed a few people I consider to be Fearless Leaders: Aiyana Ehrman, co-owner of Imagine Goods; Sam Bressi, CEO of the Lancaster County Community Foundation and Jess King, former candidate for Congress in Pennsylvania’s 11th District.

Q: Are fearless leaders born or do they grow when the environment is right?

Bressi: There might be some personal traits that are necessary. But it also requires an environment that fosters fearlessness. When I came to this organization, the community was ready for a louder presence and I felt very passionate about not wasting this moment in time. I feel the obligation to push and pull and seek.

Q: Do you feel like you needed to be a Fearless Leader to launch your new clothing line this year? It’s progressive, socially responsible and pays livable wages to the seamstresses. 

Ehrman: I had to be most fearless when we were in a dark place over a year ago and very close to closing the business. That was the moment when I needed to tap into my fearlessness. Now we’ve had a great turnaround and are showing profit and vitality. Starting a new line doesn’t take fearlessness, but staying in it when there’s no momentum takes true fearlessness. Fearlessness requires creating the momentum to turn it around at the same exact moment that you are afraid.

Q: What’s the difference between fearless and reckless?

Bressi: Fearless has a bullseye. Fearless is aiming at a very clear target. Fearless also has a plan. It readies the skills, the environment, the messaging.

Q: How do fearless leaders rebound when they fail? 

King: “If we are clearly rooted in our why, we know that when we fall short, we need to refocus on our purpose. Leadership that exercises the muscle of fearlessness is needed to make the big changes our world needs, and none of those changes are going to be easy or fast.”

Q: Can we cultivate fearlessness in others?

King: I think we can cultivate it by being transparent about what it feels like. Let’s be clear – fearless leadership is full of fear. I think it’s more accurate to say that we’re exercising the muscle of fearlessness in our leadership, which gets stronger the more we use it.

Bressi: I cultivate fearless leaders by giving the right people all the tools they need. I will take a bullet for my team even if someone fails as long as they were prepared and their intentions were at the right altitude for our community.”

Q: Is there a kryptonite for fearless leaders?

King: Ego, comparison to others and questioning your purpose. Those are all things that we can control, actually.

Q: ‘Transformation is the consequence not of something done but rather of something dropped.’ What have you had to drop in order to succeed as a fearless leader?

Bressi: Basically everything. I’ve had to let go of all the details. I’m the coach now and not the player. I’ve dropped the controls and leaned into trusting talented people.

These leaders inspire me. While some leaders continue to focus on expanding their own individual power and position, fearless leaders step out boldly for the betterment of the common good by seeing clearly and emboldening teams, communities and even movements.

Kedren Crosby is president of Work Wisdom LLC, a Lancaster-based firm specializing in organizational culture, communication, collaboration, conflict and coaching. She can be reached at kedren@workwisdomllc.com or 717-327-7780, or heard on the firm’s recently launched podcast.

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