Leadership Lessons: Practical Strategies for Building Confidence in Leaders

Confidence is an essential leadership trait that contributes to both personal and professional wellbeing. It supports resilience, strengthens community, and drives achievement. But how can leaders cultivate confidence daily, and how does it evolve over time?

Building Confidence: An Ongoing Practice

Confidence isn’t something that leaders have or don’t have—it’s developed through deliberate action and reflection. In the same way muscles are strengthened through regular use, confidence grows when it’s nurtured. Some of the best leaders we’ve worked with employ three main strategies, enhancing confidence for long-term success:

1. Reflection to Reinforce Growth

At the heart of confidence is knowing yourself. Leaders who take time each day to reflect on their performance—acknowledging both wins and challenges—develop a greater sense of what works and what doesn’t. This self-reflection helps them strengthen their understanding of themselves, encouraging growth while reinforcing confidence.

What you can ask during reflection:

• What is one thing I handled with confidence today?
• Where did I notice hesitation, and how did I navigate that feeling?

Building this daily habit helps ground you, seeing your impact more clearly, reducing the negative that can come from your inner voice.

2. Embracing Discomfort as an Opportunity

Leaders grow most when they lean into discomfort. The natural reaction to stress or uncertainty might be to pull back, but confident leaders recognize that moments of challenge often lead to breakthroughs. The key is to frame discomfort as an opportunity for your growth. By staying open to new experiences and stepping into the unknown, you will build resilience.

Consider the example of a senior leader preparing for an important board meeting. Despite lingering doubts, she embraced the challenge by preparing extensively and reminding herself of her expertise. By allowing her authentic self to shine, she navigated the meeting with confidence and earned the respect of her peers.

3. Tapping into Your Community

Confidence isn’t built in isolation—it’s amplified by connection. Leaders who lean on their communities, whether through mentorship, peer groups, or trusted colleagues, benefit from feedback and support. By actively seeking input, you’re able to check your perspective and solidify decisions, knowing that you’re not operating in a vacuum.

Building a strong network creates an environment where you feel supported in taking risks and can share the burden of challenges. This communal approach allows you to flourish, bolstering both individual confidence and collective success.

Confidence in Action: Real Leadership Experiences

To understand how these strategies play out in the real world, consider the following examples of leaders applying confidence-building practices:

Case Study 1: A CEO Who Led with Vulnerability

Meet Linda, the CEO of a mid-sized tech company. Linda was preparing for a big all-hands meeting when imposter syndrome came knocking, whispering, “Maybe you’re not CEO material after all.” She decided to address this head-on. Instead of faking her way through the presentation, she opened the meeting with, “Well, team, if I look a little nervous, it’s because I am—after all, it’s not every day you get to stand in front of the smartest people in the company!” The team laughed, and Linda’s honesty broke the ice. What started as a moment of vulnerability turned into one of the most engaging and authentic meetings her company had ever experienced.

By leading with vulnerability, Linda connected with her teams in a way that polished PowerPoints never could. Not only did she build trust, but she also reminded herself—and her team—that leadership doesn’t mean having all the answers; it means being real. Turns out, a little honesty can go a long way in building confidence.

Case Study 2: A Team Leader’s Weekly Confidence Boosters

Mike, a team leader at a global marketing agency, had a weekly ritual. Every Friday, he’d gather his team for what he jokingly called “The Swagger Hour.” Each team member had to share a win from the week—big or small. It could be anything from closing a deal to finally figuring out how to mute themselves on Zoom before shouting at the dog.

At first, people were hesitant. But as the weeks passed, the team began to look forward to these sessions, where everyone could celebrate each other’s successes. Not only did this boost team morale, but it also helped individuals realize that confidence is built from these small, everyday wins. As Mike put it, “If we don’t cheer for ourselves, who will?”

Through these weekly “confidence boosters,” Mike cultivated a culture of growth, where achievements were recognized and celebrated, no matter how quirky or small. The humour lightened the atmosphere, and the team’s confidence—and productivity—soared.

The Role of Confidence in Your Leadership Journey

Confidence isn’t about erasing doubt or achieving perfection overnight—it’s a journey of continuous growth and intentional effort. It’s about building the inner strength to navigate uncertainty with grace, courage, and determination.

To support this journey, seek out programs that focus on self-awareness, personal development, and confidence-building. Cultivate communities that encourage reflection, provide feedback, and celebrate wins. These networks act as a safety net, empowering you to take risks and embrace new opportunities with greater assurance.

Whether you’re leading a team, spearheading initiatives, or rising through the ranks, confidence serves as a foundation for personal and professional success. By committing to self-reflection, leaning into discomfort, and drawing strength from your community, you create a virtuous cycle of growth.

As you strengthen your confidence, you’ll not only achieve your own goals but also inspire those around you. Your leadership will foster trust, connection, and collective achievement, proving that confident leaders aren’t just effective—they’re transformative.

Written By: Greg Yerkes – Executive Leadership Consultant, Tall Poppies Leadership Pty Ltd