Leading with Courage: How Bold Decisions Shape the Future of Your Team
Eleanor Roosevelt once said, “Do one thing every day that scares you.” This quote has always resonated with me, especially as a leader. Boldness isn’t just about bravery in the face of fear—it’s about the willingness to take action, even when the outcome is uncertain. Bold leadership challenges the status quo, inspires others, and drives transformative results.
As leaders, the decisions we make don’t just shape our own paths—they set the tone for our teams and organizations. Being bold means trusting your intuition and stepping forward, even when you don’t have all the answers. It’s about creating opportunities for growth, innovation, and connection, not just for yourself but for those you lead.
I’m unpacking the difference between boldness and risk, the ripple effect of courageous leadership on teams, and practical ways to cultivate a culture of bold action. When we embrace the power of bold leadership we can unlock new possibilities and build a future filled with promise– for ourselves and those we have the privilege of leading.
Boldness vs. Risk: Understanding the Difference
Leadership often calls for decisions that involve risk, boldness, or sometimes both. While the two concepts are closely linked, they are distinct in their approach and mindset. Risk involves logical, calculated decision-making—assessing pros and cons, analyzing data, and determining the most strategic path forward. It’s about mitigating uncertainty while moving toward a goal.
Boldness, on the other hand, steps into a realm that often feels less secure. Boldness is about intuition and courage, about taking action even when the outcome is unclear and the path forward isn’t perfectly defined. It requires a willingness to trust your instincts, embrace vulnerability, and lead with conviction in moments when certainty isn’t an option.
Consider this: a leader might calculate the risks of launching a new product, but being bold is deciding to pursue it despite the fear of failure, driven by a belief in the idea’s potential. Boldness often pushes beyond logic, leaning into the leader’s vision and confidence to drive innovation and inspire others.
I remember a leader who decided to enter an entirely new market against the prevailing advice of analysts. The market was untested, but they believed in the unique value their company could offer. The decision didn’t just open a new revenue stream—it redefined the company’s identity as a forward-thinking innovator.
Bold leaders set the tone for teams to trust their instincts, step into uncertainty, and chase opportunities that lead to unexpected breakthroughs. It’s this combination of intuition and courage that drives growth and transformation.
The Ripple Effect of Bold Leadership
Bold leadership doesn’t just affect decisions—it shapes the entire culture of a team or organization. When leaders act boldly, they set a powerful example that inspires others to take initiative, innovate, and step beyond their comfort zones. Modeling this behavior signals to your team that courage is not only valued but expected.
When leaders embrace bold actions—whether it’s proposing an unconventional strategy, pivoting in the face of uncertainty, or simply sharing a vulnerable truth—they demonstrate that growth often requires risk. This encouragement empowers team members to follow suit, knowing that their bold contributions will be met with support rather than criticism.
However, boldness isn’t just about the wins; it’s about celebrating the effort to act. Recognizing the courage behind bold decisions—even when the results aren’t as planned—shows your team that taking risks is part of the process, not a gamble to avoid. A team that knows their bold efforts will be respected is more likely to embrace creativity, explore new ideas, and take meaningful risks.
This kind of culture fosters psychological safety—the belief that everyone can voice their thoughts, challenge ideas, and experiment without fear of judgment. It encourages resilience because the team understands that failures are simply stepping stones to growth.
When bold leadership ripples through an organization, it leads to a dynamic workplace filled with creativity, collaboration, and innovation. Teams feel inspired to take ownership of their contributions and work together to achieve outcomes they once thought were impossible.
Cultivating Boldness in Everyday Leadership
Boldness isn’t reserved for monumental moments—it’s a practice that leaders can integrate into their everyday approach. By consistently challenging comfort zones, creating opportunities for bold decisions, and fostering reflection, leaders can cultivate a culture where courage thrives.
Challenge the Comfort Zone
Growth doesn’t happen in comfort. Leaders can push themselves and their teams beyond the usual by embracing calculated discomfort. Start by questioning routines: What processes have become stale? What assumptions need rethinking? For example, instead of defaulting to tried-and-true strategies, encourage experimentation. Lead by example—take on a task that feels outside your expertise or openly share your own journey of stepping into the unknown. When teams see their leader embracing discomfort, they feel empowered to do the same.
Create Opportunities for Bold Action
Boldness flourishes when people have the chance to practice it. Create spaces for your team to generate and test daring ideas. Host brainstorming sessions where “wild” ideas are encouraged and build innovation challenges that reward risk-taking. Make these moments safe by emphasizing that the goal isn’t perfection—it’s participation. The more “at-bats” teams get, the more they’ll trust their ability to make bold moves in high-stakes situations.
Encourage Reflection and Celebration
Boldness is a muscle that strengthens with practice—and reflection. After a bold decision, take time with your team to unpack the experience. What worked? What didn’t? What was learned? Celebrate the effort, regardless of the outcome, and highlight the value of taking action. This reinforces that boldness is a team priority and normalizes taking risks as a path to growth.
By challenging comfort zones, creating opportunities to practice courage, and celebrating bold efforts, leaders set the stage for boldness to become part of their team’s DNA. Over time, this practice builds resilient, innovative teams ready to meet any challenge with confidence.
Bold Beginnings: Looking Ahead to 2025
“Whatever you can do or dream you can, begin it. Boldness has genius, power, and magic in it. Begin it now.” This timeless quote from William Hutchinson Murray reminds us of the transformative power of bold beginnings. As we step into 2025, it’s the perfect time to ask: What bold actions will you take to shape your future and the future of your team?
Bold goals don’t have to be massive undertakings—they simply require courage and intention. Maybe it’s stepping into a new role, launching a long-awaited project, or reimagining how you lead your team. Boldness starts with a vision and a commitment to take the first step, even when the path ahead is unclear.
As you set your goals for the year, challenge yourself to think not just about what you want to achieve, but how you’ll show up with boldness. How will you model courage in your decisions? How will you encourage your team to step into their own boldness?
2025 offers a blank canvas for bold leadership. Take the first step today, and let your courage inspire growth, innovation, and transformation—for yourself, your team, and your organization.
Begin it now.
Bold leadership has the power to inspire, innovate, and transform—not just teams, but entire organizations. By stepping out of your comfort zone and making courageous decisions, you can foster creativity, resilience, and a culture that thrives on bold action.
As you look ahead to 2025, take a moment to reflect: What bold goals will you set for yourself and your team? How will you model the courage needed to inspire growth and innovation? Create your vision for the year ahead and the bold actions you’ll take to lead with intention and impact. Let’s begin boldly—together.
Take a moment to reflect on how you can lead boldly in 2025. Start by challenging your comfort zones, embracing bold actions, and fostering courage in your team. To dive deeper into courageous leadership and create lasting impact, explore my keynote, "Courage as a Carry-On."
