Reboot

"Before you tell me what you do, let me ask you why you do it." Reboot challenges leaders to rethink their approach by first looking within themselves to lead effectively in business and life.

1. Radical Self-Inquiry is the First Step to Leadership Growth

Leaders are often eager for quick solutions to their challenges, but Jerry Colonna argues that true leadership begins with radical self-inquiry. This means deeply examining who you are, what shaped you, and the unresolved emotions driving your actions. Many leaders rise to the top by focusing on practical problems and solutions, but they often neglect their internal struggles.

Old wounds, such as childhood traumas or engrained fears, often surface in professional settings. These unresolved issues can lead to poor decision-making, fear-based management, or strained relationships with coworkers. Understanding these triggers is central to personal and professional growth.

Jerry shares his own story of growth. His childhood poverty in Queens left him terrified of financial instability, even after he became financially successful. This fear fueled his anxiety and desire for control, impacting both his leadership style and well-being. By looking inward, he realized he needed to address his emotional patterns to become a healthier leader.

Examples

• A CEO struggled with professional anxiety due to unresolved trauma from being bullied in school.
• Author Jerry Colonna traced his fear of failure to his childhood experiences of scarcity and conflict.
• At leadership workshops, executives uncover personal triggers that affect their workplace behavior.

2. Crisis Reveals True Leadership Character

Colonna emphasizes that moments of crisis are opportunities for profound personal and professional transformation. A leader's ability to face adversity with courage and humility defines their overall character. These challenging times force leaders to bring out their best qualities and lead others with inspiration and resilience.

Take the story of Chad Dickerson, the former CEO of Etsy. When he was fired from his position, he didn't sulk or lash out. Instead, he focused on supporting his team and ensuring a smooth transition for the company. Such behavior illustrates what Warren Bennis calls the "crucible moment," where extreme pressure shapes true leaders.

Colonna relates this principle to the Buddhist tale of Milarepa, who conquered the demons in his meditation cave by confronting and surrendering to them. Leaders can learn from this story by facing their challenges head-on, whether it means addressing toxic partnerships or dealing with personal fears.

Examples

• Chad Dickerson worked diligently even after being fired, reinforcing his values as a leader.
• Colonna advises business partners to engage in direct conversations about toxicity, like “putting your head in the demon’s mouth.”
• The Buddhist tale of Milarepa highlights the importance of facing fears to achieve inner peace and growth.

3. Embrace Stillness to Find Clarity

Modern leaders are often caught in a relentless rush, constantly focusing on the next project, task, or promotion. However, Colonna suggests that true growth happens when you pause and reflect. This stillness allows leaders to reconnect with their goals, values, and the people around them.

Colonna shares the story of a young CEO running a start-up, who worked tirelessly to avoid confronting his traumatic past. His constant busyness created a culture of toxic urgency in the workplace. By slowing down, the CEO was able to confront his fears, improve his relationship with his team, and live a more balanced life.

When leaders pause instead of rushing ahead, they create a healthier work environment. They encourage others to reflect and focus on meaningful work rather than perpetuating a culture of haste and anxiety.

Examples

• A CEO avoided addressing his painful childhood by overworking himself, harming his personal life and team morale.
• Leaders who practice daily mindfulness create space for self-awareness and improve decision-making.
• Overly busy leaders often leave employees feeling inadequate for not keeping up, harming overall productivity.

4. The Truth Always Strengthens Leadership

Colonna urges leaders to embrace truthfulness, even when it's uncomfortable. Lies, whether small or large, can spiral out of control and damage relationships, reputations, and businesses. Leaders who consistently tell the truth foster trust and stronger connections with their teams.

A powerful example involves a young business leader who was diagnosed with cancer but feared sharing the news with investors. Through Colonna’s coaching, she decided to bravely tell the truth. As a result, her investors supported her and her business more fully. This experience demonstrated that vulnerability and honesty can lead to deeper bonds and increased support.

Being truthful isn't just about avoiding lies; it’s about approaching every interaction with authenticity and vulnerability. This culture of honesty promotes understanding and builds trust in organizations.

Examples

• A business leader gained her investors’ trust when she shared her cancer diagnosis honestly.
• Colonna emphasizes the damage caused by corporate cover-ups, like VW’s emissions scandal.
• Teams become more connected when leaders lead with honesty and openness.

5. Accept Irrationality as Part of Leadership

All humans are shaped by old psychological patterns, often formed during childhood. These leftover habits or reactions, which Colonna calls "ghosts in the machine," can interfere with leadership. Recognizing and accepting this irrationality helps leaders manage their responses and embrace imperfection.

Colonna reflects on his own tendency to be overly critical, a learned habit from his father. Similarly, he worked with a business partnership plagued by unresolved parental dynamics. By acknowledging these patterns and working through them, the partners were able to function more harmoniously.

Irrationality is part of being human. Embracing it allows leaders to connect with their teams on a deeper level without judgment or frustration.

Examples

• Colonna realized his hyper-criticism mirrored his father’s habits.
• A business partnership survived once both partners addressed their underlying parental triggers.
• Accepting irrationality fosters compassion and smoother team dynamics.

6. Life's True Path is Not Always Linear

Leaders often feel the need to plan every move and remain on a predictable trajectory. However, Colonna shares that growth and fulfillment come from embracing uncertainty and being open to change. Living on the “pathless path” creates opportunities for exploration and personal transformation.

Colonna recounts his own story of breaking from the routine. Despite professional success, he reached a breaking point and considered ending his life. Instead, he embarked on a journey of discovery, letting go of rigid plans and rediscovering joy in the present moment.

Leaders who embrace flexibility and adapt to changing circumstances are better able to handle uncertainty and inspire others to do the same.

Examples

• Colonna shifted from planning to living in the moment after his Ground Zero crisis.
• Leaders benefit from adopting a “do-over” mindset to start fresh after setbacks.
• Rigidity often stifles creativity, while openness leads to innovation.

7. Learn to Live with Doubts and Fears

Doubt is a natural part of life, but leaders often push it aside, viewing it as weakness. Colonna introduces two key metaphors: the Crow and the Loyal Soldier, to explain our inner doubts and survival instincts. Instead of fighting these inner voices, leaders should learn to work with them.

The Crow represents negative self-talk, while the Loyal Soldier is the cautious voice urging self-preservation. Both can hold us back, but Colonna argues that they are also part of our humanity. Accepting and integrating these parts helps leaders grow stronger and more self-aware.

By making peace with these inner voices, leaders can cultivate resilience and approach their roles with greater self-compassion.

Examples

• Colonna chose to embrace the "Crow" rather than silencing it, recognizing its role in his growth.
• The Loyal Soldier helps people survive but can also inhibit bold decisions unless balanced.
• Leaders who accept their inner doubts often find greater mental clarity.

8. Leadership Creates Space for Growth

The best leaders are those who create environments where others feel safe to grow into their full potential. Instead of dominating through fear, great leaders act more like nurturing guides, encouraging individuality and creativity within their teams.

Colonna draws parallels to a family home where parents allow their children to freely express themselves. Similarly, leaders can prioritize the emotional well-being of their teams, promoting a culture of openness and collaboration.

By fostering trust and understanding, leaders become more like the intuitive mare in a herd of horses, who leads by sensing the group’s needs rather than exerting force or authority.

Examples

• Leaders who foster creativity and openness see their teams flourish.
• Horses choose leaders who focus on the needs of the group rather than themselves.
• Fear-based leadership stifles innovation, while trust-based leadership inspires it.

Takeaways

1. Practice mindfulness daily to pause and reconnect with your true goals.
2. Engage in radical self-inquiry by reflecting on your past and the emotions shaping your current behavior.
3. Foster an open and trusting environment in your workplace where team members feel safe to grow and share.