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3 must-have traits for courageous leadership in a post-pandemic workplace

A wide-ranging cohort of CEOs and executives weigh in on what courageous leadership really means.

By Merilee A. Kern

View original version online

While some contest, or outright refute, whether or not former British Prime Minister Winston Churchill said, “Success is not final, failure is not fatal. It is the courage to continue that counts,” it has power and is rather prophetic amid the wildly unforeseen fallout from the COVID-19 pandemic.

It speaks to prosperity not being taken for granted and the notion that failure in and of itself isn’t a death knell. Relative to business, specifically, it also evokes many questions about the very nature of courage—a concept oft characterized by the demonstration of “strength in the face of pain or grief.”

Of course, it’s presumed that successful leaders can and should inherently be courageous, but in what exact regard is courage a mission-critical managerial quality? To what extent should a leader exude courageousness versus humility? What actions, or results, exemplify how courageous–or not–a leader is? Can a wholly well-intentioned show of courageousness backfire and end up doing more harm than good?

In an attempt to clarify how this is actually defined and perceived when in practice, I took these and other questions to an assortment of business experts and leaders. The result is as eye-opening as it is inspiring.

Stick to Your Guns

By its very nature, the notion of courage connotes danger and evokes a sense of fear. Valor isn’t required without peril. Douglas A. Hicks, dean of Oxford College of Emory University, underscores that courage not only enables someone “to take risks that others fear in order to achieve something important,” but also that doing so requires a backbone. “Courage is not about sticking one’s finger in the air to see which way the wind is blowing, what others are saying. It requires both self-confidence and resolve,” he says. “CEOs show courage when they commit to keep employees on the payroll in (the) face of recession and do whatever it takes to create long-term profitability.”

Stacy Caprio of Her.CEO concurs. “A courageous leader has the ability to look at the data and make decisions, even when these decisions go against the grain of public opinion, the media, and general public panic,” she says. “Not many leaders have this ability, but a true leader is able to make decisions independent of mass fear and panic.”

Businesses that operate as a continuous, ever-evolving process (like healthcare, education, and financial management), Nicola Wealth chairman and CEO John Nicola urges that “Courage comes from the consistency of your message, your ability to support it and the loyalty of your people delivering it in all environments.” Nicola points out that moxie also manifests in a passive sense by “choosing to do nothing in the face of unrelenting pressure to act.” This is the courage of conviction, based on the principles of an individual leader, a leadership team, or the company at large.

Nicola has leaned on corporate ideology for sustenance as coronavirus-driven challenges unfold and during prior catastrophic events like the dotcom crash and the recession of 2008. “During each of these periods, we were under pressure to sell as markets dropped, to not rebalance and try and catch a falling knife, to go into cash and ride out the storm,” he says. Yet, Nicola instead mustered his courage and chose to “to do what we believed the right thing to be was”—a decision he says ultimately resulted in significant performance benefits for his firm’s clients.

How important are these kinds of instincts? Southwestern Family of Companies CEO Dustin Hills knows all too well, lamenting a time at the company when he had doubts about the sustainability of the business model and its multiple facets at that time. “Instead of having courage and actually boldly testing new models, and at the risk of my own income and reputation, I went against what my instincts were telling me,” he explains. “As a result, we went $1 million in debt and almost had to shut the business down.” Hills says, “Making the pivot to change the model to what we ended up ultimately doing with coaching and consulting was twice as hard as it would have been two years earlier when I first had the thought. But I did not have the courage to actually take action on what the numbers, the feedback, and my instincts were telling me.”

It’s understandable that Hills currently defines courage as “being afraid and taking action anyway.” He also advocates owning and being daring amid that distress. “True leaders are the ones who acknowledge they are afraid and up against a significant challenge, and yet they persevere and double down on activity during the hardest of times,” he says.

Jennifer McCollum, CEO of leadership development firm Linkage Inc., cites the findings of her firm’s research, which she says are drawn from 100,000 leadership assessments with data from more than one million leaders, revealing specific behaviors that make a leader courageous. One of the three found is: “acts in alignment with personal values in challenging, conflicting, or ambiguous situations.”

Courage shouldn’t be discounted as a key determinant of a leader’s overarching achievements. McCollum clarifies that, through the firm’s more than 30 years of study of effective leadership, “We know courage is a critical leadership practice that differentiates the most effective leaders from the rest.”

Embrace Vulnerability

Aaron Velky, CEO of Ortus Academy, believes courageous leaders also decide to be truthful and vulnerable. “Whether or not the truth is easy to share and whether or not you know what speaking the truth will create as an outcome, courage is the ability to offer up where you are and what is real, so that someone can process it individually,” he says. Bravely delivering hard messages is not enough, however, as Velky clarifies that, “When we share truth, we have to be prepared to listen, but listening is vulnerable, and that’s important too.” He says, “Courage is owning what we are experiencing. Vulnerability is sharing it—the good, bad, and emotionally jarring.”

Another facet of courageous leadership is the vulnerability to admit and share future uncertainties. In fact, Velky says that the decision to acknowledge not only what is truthful and known, but also the unknown, is another distinct decision a brave leader makes. To demonstrate courage, Velky asserts that one needs to be fiercely committed to recognizing what and how much you don’t have figured out. “Stating the unknowns mitigates the toxicity that is felt when you hide fears and the reasons to have them,” he says. “Fears are okay, the unknown is okay—once you acknowledge it.”

One business leader who’s walking that highly exposed walk of vulnerability is Mylen Yamamoto Tansingco, CEO of Cropsticks, Inc.—a social and environmentally minded B Corporation operating in the foodservice and hospitality industry. “I do not have all the answers and I’m not going to pretend I do either,” she’s refreshingly quick to admit. As a case in point, Tansingco publicly shared what Cropsticks is currently going through amid COVID-19. In her YouTube video titled “Can my business survive?,” she shared her company’s small business story in endearing, unguarded, and highly personal form. “I’m hoping to keep our community motivated and feel seen during this time,” she says, though she understands this is not without some level of risk. “I hope it doesn’t become a ‘courage fail’ after this all over,” she says. Yet she took the leap of faith into that unknown anyway.

Speaker, writer, and coach to the Fortune 500 Heather Coros contends that courage is contagious. She emphasizes that curiosity and innovation are only accessible in the brain when a sense of safety is present. “If you’re expecting your team to lean in, then they need something that feels safe to lean against. By being that safe space, you give the gift of strength and vulnerability to the entire team,” she explains. “And as we know, vulnerability is essential to highly preferred skills like transparency, clear communication, and team cohesion.” Perhaps most importantly in this post-pandemic era, Coros estimates that “Courageous leadership creates a sense of stability amidst the chaos.”

Be Undaunted, Despite

Drawing on her experiences as a stand-up comedian before entering the corporate world, Jennifer Jay Palumbo, CEO of Wonder Woman Writer, LLC, feels that being a courageous leader is accomplished by having unwavering poise. “You have to believe in yourself and your idea no matter how the person in the room reacts or not,” she says. “Trust that you’re talented and smart enough to figure it out and still accomplish the task at hand.”

Mike Zaino, president and CEO of TZG Financial, likens this kind of requisite resolve among organizational leaders to that of an underdog continuing to fight with relentless persistence despite prior outcomes. It’s “Getting knocked down seven times, and standing up eight,” he says. Yet, such doggedness should not be above reproach, as Zaino further points out that it certainly takes courage to not just hear—but accept—constructive criticism. “You’re either learning or you’re dying,” he says.

That idea is shared by Mercy Project, Inc. CEO Chris Field. He believes that, for courageousness to be a leadership asset, it must be a concerted choice—a daily decision—rather than happenstance. “Courage is a muscle, one we must exercise and grow by being courageous . . . one decision at a time,” he submits. “Courage takes many forms, but none of them happen by accident.”

While conveying courageousness certainly takes chutzpah, Women Presidents’ Organization CEO Camille Burns cautions that it’s important to exude confidence without arrogance. “I think people often confuse risk-taking with being courageous,” she says. “Taking a risk is a bold move. But it is even more courageous to fail, to accept that something you tried did not have the outcome you wanted or expected.”

Even so, risk-taking does certainly take its fair share of bravado and duly illustrates leaders with this attribute. Tim Chen, cofounder and CEO of NerdWallet, points out the prospect for growth moments during times of crisis, namely the current one. He appreciates the extent to which COVID-19 has ushered in a defining time for business leaders. “Even though we’re navigating unprecedented uncertainties, I see this as a huge opportunity for the type of courageous decision-making and smart risk-taking that leads to immense personal and professional growth,” he says, “In fact, I can track most of my greatest periods of personal growth to a prior crisis.”

Chen’s colleague Kelly Gillease, NerdWallet CMO, sees an opportunity for courageous risk-taking with frequency. “Great leaders exhibit courage in small ways every day by encouraging risks and bigger thinking or being vulnerable and empathetic when a situation calls for it,” she says. Gillease strives to model this by “having a willingness to call out the elephant in the room.”

Attitude is also the name of the game. It’s important to temper chutzpah so that it doesn’t come across as overly audacious. Haughty demeanors aren’t particularly welcomed in business, but this kind of disposition can veritably doom an executive’s image—especially when attempting to navigate a gaffe. “When someone does not acknowledge what they do not know, or the mistake they have made, it is a courage fail,” Burns warns. “Sustained naivety is when you deny the fail, or when you try to blame it on someone else or block out the writing on the walls. If there is no learning derived from failure, there is no achievement. Then, it is a double failure.”

Courageous business practices are guided not just by guts and grit, but also by focused and unwavering guidance that keeps a leader on course. Just ask Field, who muses, “Courage is knowing our North Star and regularly checking to make sure we’re still headed there.”