The Brave CEO: What Courage Looks Like for Today's Leaders

October 25, 2018 | Chris Caputo


Take a snapshot of the courageous modern business leader. What you’ll see in the frame is not a board puppet who quietly hands down decisions that everyone disagrees with, but everyone expects.

And we’re certainly not talking about an untouchable dictator—sealed away in a glass office, listening to no one, essentially walking the company down the plank.

So, how does the bold CEO of today operate within the culture of the company—and in an era of digital transformation—in a way that bodes success?


True courage in leadership rides the waves with balance—neither completely thrown by employee dissension and doubt, nor duped by flattery. The bedrock of forward-thinking executives is chin-up confidence that fixes its eyes on goals and takes steady steps of wisdom.

Don’t misunderstand. This is not completely blind courage, some kind of ridiculous daily throwing of all caution to the wind, refusing to hear the rest of the c-suite. Instead, it’s advancing in evidence-based best business practice when that makes sense, plus being sure-footed enough to take some risks when no one else is. It’s exhibiting boldness when the heart says, “Go for it.” It’s savvy. It’s smart.

Graham Poston writes in The Business Times Hub ,

“What distinguishes the great from the good transformational leaders is an ability to find 'BOTH-AND' or win-win solutions to seemingly competing priorities. For example, they find a way to enhance the customer experience while simultaneously reducing the cost to service through digitization. They focus on the short term while establishing the building blocks for tomorrow's success.”

The modern corporate world is a wild ride. And a CEO that demonstrates constancy—a reliable certainty that knows what move to make and why—will provide a courageous stability that is invaluable for strong business.


Sometimes business bravery means sticking reputation in the back seat. Even among leaders, it’s a rare person who can state sincerely that in the end, when there’s a brave move to make, they really don’t care what the rest of the company or the public or the investors or their friends think.

Let’s pose a guiding question here: What are you looking at?

The safe CEO has eyes on certain things—the board’s opinion, the financials, fault-finding reviewers, history, and the W and T sides of the most recent SWOT analysis.
The revolutionary CEO finds the strength to look past and above all that—acknowledging realities, but moving on to bigger and better things.

Get your gaze up. Demonstrate by your behavior not what everyone knows you already are, but what you want to inspire them to be.


Yes, the subtext of setting aside reputation is vulnerability. Augusto Giacoman of strategy+business explains, “Embracing vulnerability means having the courage to face your fears and the wild uncertainty of the future. A vulnerable leader decides that she will meet that uncertainty with an open heart, willing to experience all the ups and downs that come with it.” Smart CEOs know that transparent, authentic, I’m-not-perfect openness is actually an admirable quality that very much endears leaders to the rest of the company.

Being real with your people inspires corporate allegiance. And this is what you want. Daresay’s Malin Sundlin describes the advantage of having a supportive team behind you as you forge into the dark: “It’s easier to be courageous when the people implementing your decisions are on board.”

How? Effective change management means listening to all levels of employees. Give employees voice, try their ideas, implement the effective, workable ones, and you’ll build loyalty. If you’ve been open from the start about expecting crazy ups and downs, people will come along with you because they respect that honesty.

Admit mistakes. Be yourself. And then rally your most supportive peers and change things up.


Brace yourself, CEO. Because courage doesn’t somehow ensure smooth sailing. Audacious moves are pretty guaranteed to bring some hard days, for you and your team. Your ability to weather industry or company storms is exactly what will brand you as either a reckless renegade or a daring visionary. Make your move—and then hang on tight.

This kind of sustained fortitude—stamina—is what people really look for in leaders. Not the quick flash of boss brilliance, but the long-term, over time, proven ability to take an enterprise and turn it into something admirable, something great.


To make courage a phrase, not just a word, we often speak in terms of “the courage to _____.” And for modern CEOs, what often goes in the blank is, “change.” The courage to step out. Try something completely different. Turn the corner. Venture into a new market segment. Rock the boat. Expand audience. Challenge industry status quos. Incorporate new voices. Leap out of the box entirely. Re-brand.

"No one experiences transformation by doing more of the same."

No one gets ahead by standing still. No one experiences transformation by doing more of the same. In other words, successful CEOs cannot be afraid, as Graham Poston argues, “to challenge the very organizational systems, processes and culture that have underpinned their past success.” Today’s CEO is thinking about 2030 and 2040, the next potential CEOs, the possibilities. 


So, you’ve got all this—inside. Fantastic. And internal courage is one thing. But transmitting that courage through inspiring communication, so that the rest of the company is armed and ready to follow you into brave new industry worlds—this is another whole deal.

Fabulous ideas packaged poorly will never pull people together to move forward. But a positive announcement of a transformation, altered direction, new products, or a clarified mission can work very well and even expand future opportunity for growth. It’s all about the manifestation of leaders’ courageous vision. Want good reception? Introduce innovations with excitement and then follow through with enactment of those changes.

William George of Harvard Business Review’s Ascend offers a great summary:

“Courageous leaders take risks that go against the grain of their organizations. They make decisions with the potential for revolutionary change in their markets. Their boldness inspires their teams, energizes customers, and positions their companies as leaders in societal change.”

Topics: Future of Work Digital Leadership

About the Author
Chris Caputo

Chris Caputo is a strategic marketing technologist with over 20 years of BtoB, BtoC and agency experience. An accomplished strategic marketing leader, Chris has extensive experience architecting marketing communication plans, digital marketing roadmaps, user experience planning, and developing digital customer acquisition, conversion and retention strategies. Having led BtoB marketing departments for a variety of companies and digital agencies, Chris has developed a rounded set of skills that include a depth of multiple marketing disciplines (PR, Advertising & Direct Marketing) overlapped with Digital, Print and Broadcast channels.

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