Daring to Lead: Transforming City Management Through Courage

Over the past week, we’ve delved deep into Brené Brown’s “Dare to Lead,” exploring how its four key skills apply to the challenging world of city management. As we wrap up this series, let’s bring these threads together and envision what truly daring leadership can look like in our municipalities.

The Four Pillars of Courageous Leadership

Let’s recap the four crucial skills we’ve explored:

1. Vulnerability: The willingness to show up and be seen, even when there are no guarantees.
2. Living into Our Values: Identifying and operationalizing the beliefs that we hold most important.
3. Braving Trust: Choosing to make something important to you vulnerable to the actions of someone else.
4. Learning to Rise: The ability to get back up after failure and grow from the experience.

In city management, these skills aren’t just theoretical concepts—they’re practical tools for navigating the complex, often turbulent waters of municipal leadership.

The Symphony of Courageous Leadership

Imagine a city manager who embodies these four skills. They’re not a superhero, immune to doubt or failure. Instead, they’re deeply human, and that’s precisely their strength.

When faced with a controversial decision, they’re vulnerable enough to admit uncertainty and seek input (Vulnerability). They base their ultimate decision on clearly articulated values that guide their administration (Living into Our Values). They’re transparent about the decision-making process, fostering trust with both their team and the public (Braving Trust). And when inevitably faced with criticism or setbacks, they demonstrate resilience, learning and growing from the experience (Learning to Rise).

This isn’t just effective leadership—it’s transformative leadership.

The Real-World Impact

In my years of coaching high-level leaders, I’ve seen firsthand how these skills can revolutionize organizations:

• Vulnerability leads to more innovative problem-solving as team members feel safe sharing ideas.
• Living into Values results in more consistent decision-making and clearer communication with stakeholders.
• Braving Trust creates stronger relationships with staff, elected officials, and the community, facilitating smoother implementation of initiatives.
• Learning to Rise builds a more resilient organization that can weather crises and emerge stronger.

The Challenges and the Rewards

Make no mistake—daring to lead in this way isn’t easy. It requires courage, consistency, and a willingness to go against the grain of traditional “strong” leadership stereotypes. You’ll face skeptics who mistake vulnerability for weakness, or who see values-based leadership as inflexible.

But the rewards are immense. You’ll build a more engaged, innovative team. You’ll foster greater trust with your community. You’ll make decisions you can stand behind, regardless of outcome. And you’ll develop the resilience to face any challenge that comes your way.

Your Dare to Lead Journey

As we conclude this series, I encourage you to reflect on your own leadership journey:

• Where have you already shown courage in your role?
• Which of these four skills resonates most with you? Which feels most challenging?
• What’s one small step you can take this week to lean into courageous leadership?

Remember, this isn’t about perfection. It’s about progress. It’s about choosing, day after day, to show up fully in your role, to lead with integrity, to foster trust, and to bounce back from setbacks.

A Personal Note

As someone who has faced his own leadership crucibles, who has tasted both bitter failure and sweet success, I can tell you this: The path of courageous leadership is not always easy, but it is always worth it. It’s the path that will not only transform your effectiveness as a leader but will also bring greater fulfillment and purpose to your work.

At HaltingWinter, we’re committed to supporting city managers on this journey. Our coaching isn’t about quick fixes or one-size-fits-all solutions. It’s about walking alongside you as you develop these crucial skills, providing support, perspective, and strategies tailored to your unique challenges. If that would be a help to your leadership journey, reach out.

The Dare to You

So here’s my dare to you: Choose courage. Choose to be vulnerable, to live your values, to brave trust, and to rise after falls. Choose to transform not just your leadership, but your entire city.

The challenges of city management are great, but so is the potential for positive impact. By daring to lead with courage, you can create more vibrant, innovative, and resilient communities.

What will your courageous leadership story be? Share your thoughts, experiences, and aspirations on our LinkedIn page. Let’s build a community of city managers who dare to lead.