Courageous Leadership Playbook: Lessons 

What Courageous Leadership Looks Like Today

“Fortune favors the brave, not the cautious.”

The Courageous Leadership Playbook as reported in the Sept-Oct, 2025 cover story in Harvard Business Review highlights several lessons worth revisiting. In these largely unpredictable & volatile times, the author points out that we develop courage in five (5) ways.

Also, why do some leaders make daring moves while others hesitate?

Additionally, are you born with courage, or conversely, can courage be taught?

Why Courageous Leadership Demands Bravery as a Choice

Understanding the HBR Definition of Courage

HBR defines courage as a willingness to take bold, risky action to serve a purpose that you perceive to be worthy, usually in the face of an abiding fear.

Managing Risk Without Avoiding It

Firstly, as fellow leaders, maybe this means leaning into some sort of physical challenge. Secondly, perhaps in the moment, maybe this means making yourself emotionally vulnerable. Thirdly, maybe it means risking your social or economic standing for your moral beliefs. Finally, maybe it means simply championing new, unorthodox ideas or approaches towards a business issue. Experts suggest the best way to overcome anxiety about uncertainty is risk management. Note, that I didn’t say risk aversion. As the HBR article points out, some pundits prefer an intelligent gamble based on careful deliberation and preparation. By now, you’ve heard the old adage, “Luck is when preparation meets opportunity.”

“Luck is when preparation meets opportunity.”

Maybe you are considering whether to fund a new business or add an additional product or service offering. After all, it makes sense to do some sort of cost/benefit analysis doesn’t it? Basically, trusting your gut. When I was getting my MBA, a popular “go-to” was “given what we think we know, what is the worst outcome that can happen?”

All things considered, under volatile, uncertain, complex and ambiguous (“VUCA”) conditions, when possible outcomes are both numerous and unknown, most folks feel a loss of control and fear. Thos often leads next to flight-fight-or-freeze and by extension paralysis. On the other hand, brave leaders lean in, by reclaiming agency and flight.

How Courageous Leaders Create a Positive Narrative

Go risk hunting

• Identify and mitigate the challenges and threats that you face. Look for the positives that inspire action.

Find a moral quest

• If you can, recast your work and in alignment with the heroic pursuit of values that you and/or your organization hold dear. The more aligned with moral conviction, the better.

Call upon your faith

• An adaptive way of coping is to draw on your belief in a higher power.

“God take an interest in the doers.”

Cultivating Confidence through Mastery and Preparation

Master our craft

• Wasn’t it Malcolm Gladwell who spoke about mastering complexity with 10,000 hours? If I exhibit great competence through repetition, I’m better equipped to grapple with complex and ambiguous challenges. Coach Ryan Day of The Ohio State University Football Team admonishes us to “play the way you practice.”

Train deliberately

• Apply best practices until they become second nature. Admired golfer Ben Hogan used to coach a “golf swing built for pressure.” Be the expert at your craft, whatever that may be and have your decisions and direction hold up under stress.

Assemble a large toolkit

• Deploy a broad array of tools in your arsenal. During batting practice, Pete Rose, one of the best to ever play the national pastime, would often practice situational baseball when taking practice at-bats rather than just aimlessly hitting baseballs. “Man on first; one out, hit behind the runner….”

Focus on what you can control

•  Break big tasks into smaller chunks. Focus on the process, not the outcome. “Today, we’re not going to talk about what we’re going to accomplish. We’re going to focus on how we’re going to do it.”

Taking Small Courageous Steps in Uncertain Environments

Fire Small Bullets Before Cannonballs

• Author Jim Collins admonishes his disciples to fire small bullets (low risk) before cannonballs.

Evaluate objectively

• Continuing with the Collins analogy, by firing small bullets first, begins to offer clarity and amplify observed empirical evidence of pending success or failure.

Let meaning emerge

• Interpret the data and the resulting patterns. Deploy good situational awareness. Have I seen these results before and if so, how did that work out for me? Create a hypotheses and choose the best one. Build, refine and adjust.

Interpret in motion

• Amazon calls this a “two-way door”—one door that you can walkthrough but back out if the situation calls for it.

Building Connection Because Courage Is a Team Sport

“There are few lone heroes. Courage is a team sport.”

You want to find supporters and critics

• Turn to allies for an emotional boost. When facing uncertainty or ambiguity, this kind of support becomes even more important.
• Turn to critics when you want to pressure test your hypothesis or approach. Let them poke holes in it. 

Assess resources

• You can’t know everything about everything. When in doubt or unsure, bring in an expert. If a sounding board would be helpful, or if you would like to learn more about the Courageous Leadership Playbook, please contact me here.
• Accept feedback. Have the cheerleaders provide a confidence boost. Have the critics judge your choices. As a result, you’ll have more confidence in the choices that you make.

Stay Calm

Practice self-care deliberately and consistently

• Sleep. Diet. Exercise.

Use rituals to stay centered

• These help keep you centered.

Reframe the situation objectively

In MBA world, we framed  our outcomes as optimistic, realistic and pessimistic. Earlier, we talked about the worst possible outcomes. Conversely, ask yourself, what could go right?