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Finding the Courage to Be Bold

Updated: Nov 5, 2021

Stepping in, speaking up, and advocating change

I attended an Equity, Diversity and Inclusion (ED&I) training session for a board I sit on. The facilitator set expectations of the bold and challenging work that was needed to realize equity. Our ED&I work takes each of us being courageous, at times boldly so. Let’s look at how we can work on our courage competency.

Over the last five years, I’ve been working intimately with hundreds of leaders as their executive coach. This work has enabled me to see and experience different personalities and leadership styles. I’ve been able to tap into their thinking, and emotional responses to major decisions and actions.

Doing this work has made me reflect on my own leadership style and lessons. One thing I wish I’d done differently, when I worked in corporations, is to be more bold. I chose to play it safe and take a political position that protected my role. This affected the way I showed up, and whether or not I spoke up. To lead and succeed in these times, our opportunity is to be more courageous.

Leading Under Pressure

When we see changes in our professional demeanor, it’s a safety versus risk situation. When relationships and positions are safe, it’s easy to be confident and take risks. When belonging or career stability become uncertain, worry and stress increase.

In stressful situations our ability to be flexible is diminished. We likely won’t show up the way we’d really like to. We are less filtered, and our emotions seep out. The more self-aware we are of our mindset and emotional reactions, the more we can adjust to the situation to achieve our best selves, particularly in the workplace.

I can now see and better understand where I held myself back, and my execution was flawed. I showed up with attributes that weren’t what excelled me in my career. Some of you may recognize these attributes in yourself; self-critical, emotional, reactive, impulsive or risk averse. The key attribute of executing courage, and key ingredient to Leadership Presence, is composure.

Tapping into Courage

Courage is about stepping in, speaking up and advocating change. Depending on the situation, there’s different courage to be drawn upon. Knowing how to show up and which type of courage to use is mastered with practice, and it often comes after faltering in execution at first.

Our guest contributor, Bill Brown, the Principal of Brown Executive Coaching, says, “Operating outside your natural leadership style is draining and requires courage. You must embrace fear of failing. If you preserve your integrity and stay aligned to your leadership brand, the recovery will be easier. Imperfect impact outweighs doing nothing at all.”

“Courage is not the absence of fear, but rather the judgement that something else is more important than fear.”― Ambrose Redmoon, author

Stepping in with courage can be done boldly or carefully. Bold courage is about stepping in, challenging yourself and using your voice confidently, saying, “I need to see change in the following areas.”

Bold courage can also often be connected to values, passion, or time sensitive change. When you apply bold courage, you could run the risk of deviating from your personal brand and your credibility could be compromised. Being bold likely involves feeling alone because you’re often standing alone.

On the flip side, careful courage is softer, where you might say, “I’ll try again tomorrow.” It may incorporate teaming, delegation and letting other people take the reins. Careful courage is more patient and adaptive in its application. It’s a lighter approach that involves being strategic, organizationally savvy, and anticipating internal politics.

Being Courageous

The courage competency is one of the important leadership skills. It’s an enabler to strategic skills, operating skills, and delivering results. Courage may mean: giving upward feedback on a decision or action you disagree with; advocating a change in which you stand alone; taking on a tumultuous situation knowing your popularity may falter; or saying something especially important, yet extremely uncomfortable.

I asked two experts in our network about their reflections on courage.

Aymen Dewji, founder of ShiftRight Consulting, is a change consultant who has led global transformation projects for Fortune 500 companies. When I asked her about how she helps clients embrace courage, she said, “The philosophy of our company embraces the idea that organizations don’t change, people do. When making any transformation, no matter how large or limited the impact, we start with an understanding of how this will impact your most important asset: your people.” She added, “It isn’t always possible to say what needs to be said at the right time. However, it is always possible to say it in the right manner. Through the discussion of what will be difficult, we validate what will be possible as the outcome of the transformation. Difficult conversations are inherent. We start tough conversation in an area of agreement with both parties. It doesn’t have to be perfect; it just must start with an ability to acknowledge each party’s values.

Bill, shared more of his insights and says, “Leaders need to be consistent. Circumstances may necessitate bold moves that seem out of character. Consistency and integrity are cornerstones.” He continued, “Separate the problem from the people. Be hard on the problem, soft on the people. Being curious versus assumptive enables both outcomes. It’s essential to recognize that sensitivity is defined by the receiver and honesty is defined by the sender/leader. The 'honest’ messages should be vetted against two questions:

1) What is my purpose in sharing this with the receiver?

2) What do they need to do once they receive it?”

How does Bill help his executive coaching clients be courageous? “I use the Time Travel technique. Take them back to former success exploring what they learned, how they felt, and the outcomes. Then pull them forward to envision what success will look and feel like on the other side. Finally, move to the present and support them building an action plan.”

What’s Next

As an entrepreneur building a company, I’ve been using my bold and soft courage skills. I continue to develop my courageous skills.

Each of us has an opportunity to step in with bold courage in our ED&I work. This work is focused on:

● Challenging our own biases;

● Speaking up and acting on ED&I progress;

● Advocating for those who need our support; and

● Speaking up on matters attached to values, credibility, and fairness.

What do you need to courageously work on?

About Our Guest Contributors

Aymen Dewji is the Founder and Managing Partner at ShiftRight Consulting, a Human Capital firm with a passion for change! She brings over a decade of

experience managing large scale transformative change for Fortune 500 organizations. Aymen is a growth focused entrepreneur who identifies as a Pan-Asian professional and a leader of change. Her keen understanding of what drives adoption during the height of organizational influx has earned her the respect and trust of her clients and peers. Her diversity journey began early in her career and helped her to develop deep perspective on the opportunity to face change courageously.

Bill Brown, Brown Executive Coaching, is a CEO turned Executive Coach who champions leaders to courageously discover and develop untapped potential and reach higher. He has 30 years in leadership positions with experience scaling business in several industry. Across all his work is a customer-centric growth orientation, building leadership teams that own our mission and leveraging strengths to realize goals. Bill knows the biggest barrier to success is confidence. He helps is clients achieve confidence by accessing action, mastery and courage.


Lisa W. Haydon is a business leader and entrepreneur with over 30 years of operational experience leading teams in banking, capital markets, technology and professional services. Lisa’s instinct for sorting through business complexities, understanding distinctive leader personalities, and realizing results compelled her to leave a corporate career and become an entrepreneur.

Her company, Pivotal Growth, introduced a technology tool for leadership development assessment and planning. The suite of tools offers diagnostic capabilities to synthesize and accelerate people performance.

Lisa’s skills and the Pivotal Growth product help companies enhance their performance and support leaders achieving greater confidence and success.

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