Insights

HOW TO LEAD FROM THE INSIDE-OUT

A man in a suit stands at a podium, seen from behind, addressing a large audience in a dimly lit auditorium with spotlights shining down from above.


SERIES #1:

How Self-Awareness is Reshaping the Character of CEOs and Executives

As an advisor to CEOs, Boards and senior executives, I have observed how the pressures facing leaders — especially those in public service-continue to mount. In a rapidly changing world where complexity, defensiveness, and scrutiny are the norm, the leaders who stand out are not those with the loudest voices or the longest resumes, but those who have actually done the hard work on themselves first. Leadership, at its core, starts from the inside out.

What is Inside-Out Leadership and Why Does it Matters

Leadership isn’t something you put on like a uniform and it’s not a title. It is something that grows from within. Too often, leaders are measured by titles, accolades, or the size of their organizations. But in my work with executives across sectors, I’ve seen that the most effective CEOs and executives begin by better understanding themselves. They recognize their strengths and blind spots, and they’re honest about what drives their decisions, particularly when no one is watching.

Inside-out leadership isn’t about perfection. It’s about the willingness to examine your own motives, to ask yourself tough questions, and to build a foundation of integrity that holds up under pressure. This approach means your values aren’t just talking points, they’re the compass that guides your choices, especially when the path isn’t clear.

The Practical Side of Self-Awareness

Self-awareness is not a static trait-it’s a discipline and a practice. Leaders who are self-aware make it a habit to reflect on their actions and decisions. They carve out time to ask themselves: What went well today? Where did I miss the mark? What can I learn from this experience? This kind of reflection isn’t self-indulgence; it’s the groundwork for better leadership.

Practical tools for building self-awareness include:

  • Journaling and writing down your thoughts, decisions, and reactions can reveal patterns over time. Journaling helps track progress and recognize recurring blind spots.
  • Seeking feedback, because the best leaders don’t just rely on their own perspective. They invite honest feedback from trusted colleagues, mentors, and even team members. This willingness to listen is a mark of confidence, not insecurity.
  • Continuous learning, self-awareness, and curiosity. They read, attend workshops, and stay open to new ideas. They know that growth is a lifelong process, not a checkbox on a resume. 

Emotional Intelligence and Vulnerability

A key part of self-awareness is emotional intelligence, the ability to understand and manage your own emotions, and to recognize and influence the emotions of others. Successful leaders with high emotional intelligence are better equipped to handle stress, navigate conflict, and inspire trust.

But EQ also means embracing vulnerability. Leaders are often expected to project confidence and certainty, but real respect is earned when you can admit mistakes, acknowledge limitations, and ask for help. This kind of openness builds trust and sets the tone for genuine relationships across your organization.

Leadership Happens in the Quiet Moments

It’s easy to think of leadership as a series of big decisions or bold moves. But in reality, true leadership often happens in the quiet moments, those times when you pause to reflect, to listen, or to reconsider your next step. It’s in these silences that clarity emerges from chaos, and where you find the courage to act in alignment with your core values.

This is what I call emotional fortitude, which is the ability to maintain clarity under pressure, not just to stay calm. Leaders who cultivate this inner strength are able to respond thoughtfully, rather than react impulsively, even when the stakes are high.

Building Trust Through Authenticity

Teams and organizations don’t just follow leaders, they follow people they trust. Trust is built when leadership is consistently aligned with their actions and values. Authenticity is not about oversharing or trying to be liked by everyone; it’s about being genuine, consistent, and reliable. Encouraging open communication and inviting others to be themselves creates a culture where people feel safe to contribute ideas, raise concerns, and take risks. This kind of environment doesn’t just boost morale, it drives results.

The Ongoing Journey

Inside-out leadership is an ongoing journey, not a destination. It’s about the daily choice to examine your motives, to learn from your experiences, and to act with integrity-even when no one is watching. The leaders who invest in this inner work are the ones who build organizations that last and teams that thrive.

In the next article, I will dig deeper into the practical approach to the psychology of leadership and how understanding what drives people (and yourself) can motivate improved decision making, strengthen teams and improve the bottom line of an organization.

Crawford’s journey has given him a profound understanding of the pressures faced by those in top leadership positions. He recognizes that beneath the confident exterior, many CEOs grapple with self-doubt and the weight of their responsibilities. Drawing from his experiences in high-stakes decision-making as a fire chief and city manager, Crawford creates a safe space where executives can openly discuss their concerns without fear of judgment.

What sets Crawford apart is his practical approach to the psychology of leadership. Rather than relying solely on theoretical models, he draws on real-world experiences to help executives navigate complex leadership issues. This hands-on methodology resonates deeply with executives who are looking for actionable insights rather than abstract concepts.

Crawford addresses the challenge many face in receiving candid feedback. He provides a valuable external perspective, offering honest, constructive input that helps leaders identify blind spots and areas for growth. This approach enables CEOs to make more informed decisions and lead with greater authenticity.

Addressing CEO Challenges
The demanding nature of a leadership role often strains personal relationships and work-life balance. Crawford, having navigated his own transition to the private sector, guides leaders in managing these pressures effectively. He helps them strike a balance between driving organizational change and maintaining personal well-being, ensuring they can lead sustainably over the long term.

For those grappling with the complexities of leadership transitions, Crawford’s diverse background proves invaluable. He helps them navigate not just the operational aspects of change, but also the personal and emotional challenges that come with it. This comprehensive support allows leaders to approach transitions with greater confidence and clarity.

Navigating Transition and Legacy Concerns
Crawford also addresses the profound question of legacy that many contemplate. He encourages leaders to align their actions with their values, helping them build a legacy that extends beyond mere business achievements. By acting as an accountability partner, he empowers CEOs and executives to make decisions that reflect their true aspirations and have a lasting positive impact.

Crawford’s journey has given him a profound understanding of the pressures faced by those in top leadership positions. He recognizes that beneath the confident exterior, many CEOs grapple with self-doubt and the weight of their responsibilities. Drawing from his experiences in high-stakes decision-making as a fire chief and city manager, Crawford creates a safe space where executives can openly discuss their concerns without fear of judgment.

What sets Crawford apart is his practical approach to the psychology of leadership. Rather than relying solely on theoretical models, he draws on real-world experiences to help executives navigate complex leadership issues. This hands-on methodology resonates deeply with executives who are looking for actionable insights rather than abstract concepts.

Crawford addresses the challenge many face in receiving candid feedback. He provides a valuable external perspective, offering honest, constructive input that helps leaders identify blind spots and areas for growth. This approach enables CEOs to make more informed decisions and lead with greater authenticity.

Addressing CEO Challenges
The demanding nature of a leadership role often strains personal relationships and work-life balance. Crawford, having navigated his own transition to the private sector, guides leaders in managing these pressures effectively. He helps them strike a balance between driving organizational change and maintaining personal well-being, ensuring they can lead sustainably over the long term.

For those grappling with the complexities of leadership transitions, Crawford’s diverse background proves invaluable. He helps them navigate not just the operational aspects of change, but also the personal and emotional challenges that come with it. This comprehensive support allows leaders to approach transitions with greater confidence and clarity.

Navigating Transition and Legacy Concerns
Crawford also addresses the profound question of legacy that many contemplate. He encourages leaders to align their actions with their values, helping them build a legacy that extends beyond mere business achievements. By acting as an accountability partner, he empowers CEOs and executives to make decisions that reflect their true aspirations and have a lasting positive impact.