The Journey from Accidental to Intentional CEO

In this powerful and reflective conversation, Tom and Adam unpack the experience of transitioning from running a business by chance to intentionally leading one as a CEO. They reflect on their recent morning workshop, the dynamics of energy in virtual versus in-person sessions, and the importance of intentional leadership. They also dive into how mindset shifts around leadership, hiring, and personal healing influence business growth.
Throughout the episode, they discuss the themes of awareness, permission, and evolution in both business and personal relationships, sharing real-life coaching examples and their own leadership journeys.
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Key Topics Covered
☀️ Morning Energy & Virtual Workshop Reflections
• Tom and Adam share insights from their recent morning online workshop, observing how time of day and participant energy shape the session’s dynamics.
• They discuss the difference between morning and evening attendees — morning participants often being more intentional, sacrificing other commitments like family or fitness to show up.
🧭 From Accidental to Intentional CEO
• The duo opens up about how they both stumbled into their CEO roles, initially treating their business as a side hustle before realizing they had built something real.
• They emphasize the journey of accepting leadership roles and defining their responsibilities as CEO and COO.
• The transition from doing everything themselves to building a team and defining the business intentionally took 3–5 years.
🔑 The Power of Permission & Intention
• Many accidental CEOs struggle with giving themselves permission to succeed, lead, and delegate.
• One client example: an architect who became an intentional CEO by investing in his team, advertising, and trusting the process of cause and effect.
• Healing from past limiting beliefs and stepping into the CEO mindset is a key part of the transformation.
❤️ Healing Through Relationships
• Tom shares the importance of the relationship with oneself and how personal healing impacts leadership and team relationships.
• A powerful coaching example highlights a client who worked through past relationship wounds to show up fully in a new, healthier relationship.
• The conversation explores how unresolved past experiences resurface until they are addressed and integrated.
🧰 The "What Went Right, What Went Wrong, What Do You Need Help With?" Framework
• Adam explains how this simple three-question framework, inspired by his mentor, helps CEOs reflect on their wins, challenges, and areas where they need support.
• This tool encourages business owners to actively ask for help rather than staying stuck in their own heads.
🛠️ Building and Managing a Team
• The 40/60/80% employee competency model:
o 40% competent: Task-doers who free up the CEO’s time but require training.
o 60% competent: Core team members who perform well independently.
o 80% competent: High performers who may eventually outgrow the role and need to be challenged or promoted.
• When to hire specialists and how to ensure hires are aligned with business needs rather than personal gaps.
🔄 Letting Go of Misaligned Team Members
• A real-world coaching story where a client made the difficult but necessary decision to shift a misaligned employee to a different role or release them.
• The key lesson: act in the best interest of the business, not personal comfort.
🕰️ The Value of Reflection Time
• The workshops provide business owners a rare space to pause, reflect, and strategize away from the daily grind.
• Creating intentional space is essential for leadership growth.
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Key Quotes
"Many accidental CEOs are just waiting for permission to succeed."
"You’re packing your suitcase for your journey — even if it’s filled with things you’re not sure you’ll need yet."
"The most important relationship is the one you have with yourself."
"Hire for what the business needs, not what you feel you’re lacking as a leader."
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Resources Mentioned
• Accidental CEO Workshops: Weekly workshops (morning, afternoon, evening, and in-person on Long Island) where accidental CEOs can pause, reflect, and grow.
• Morning Meeting Book: A resource to help CEOs structure their day and leadership practice.
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Call to Action
If you resonated with today’s discussion and are looking for a supportive community of fellow business owners navigating the same challenges, join one of our Accidental CEO Workshops. Find the schedule and sign up at the link in the show notes.
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Connect with Us
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