When Leaders Can't Lead: The Courage Crisis in Education with Phil Roberts
What happens when the most dedicated leaders become their own worst enemies?
After 21 years as a principal and 30+ years in educational leadership, Phil Roberts has seen it all from transforming failing schools into thriving communities to coaching drowning executives back to shore. Now, as an ICF-accredited coach and consultant to Australia's independent and Jewish education sectors, Phil reveals the uncomfortable truth about leadership that no one talks about.
In this raw conversation, Phil shares the story of a Melbourne school leader who's sacrificing everything family, health, and ironically, his ability to lead—in pursuit of serving others. It's a pattern Phil sees repeatedly: the most altruistic leaders often need the most help.
Key Takeaways:
Phil drops truth bombs about the coaching industry itself, including the stark difference between knowledge and wisdom, why life experience trumps certifications, and the years-long journey to land C-suite clients. His advice to aspiring coaches? "Buy your time. Don't rush into being a 20-something coach unless you've got real experience to draw on."
Whether you're a coach working with educational leaders, an executive struggling with work-life balance, or someone considering the leap into coaching, this episode delivers hard-won insights from the intersection of leadership, education, and personal transformation.
The conversation peaks when David challenges the notion of compartmentalized coaching: "You can't just coach half of somebody. If you're gonna coach them, you have to coach the whole person." Phil's response will change how you think about leadership development forever.
Building a Coaching Business with Intention – Not by Accident
What does it really take to build a coaching business that creates deep impact without desperate selling? And how do you design a practice around the life you want – not just the income you need?
In this episode, David sits down with Eileen Rogers, a former CEO who built and sold a multimillion-dollar marketing company after 40 years before transitioning into executive coaching. Eileen is one of only 500 people worldwide trained by Brené Brown to facilitate Dare to Lead™, and she uses the Enneagram alongside her decades of leadership experience to help executives transform from armored to courageous leadership.
This conversation goes deep into the realities of building a coaching business, the good, the challenging, and the intentional choices that separate thriving coaches from struggling ones.
In this episode, you'll discover:
Whether you're just starting your coaching journey or refining an established practice, Eileen's wisdom on building with intention, serving from abundance, and creating sustainable impact will shift how you think about your business.
About Eileen Rogers:
Eileen Rogers built and sold a marketing company after 40 years before founding One Creative View, where she works as a leadership coach and advisor. She's one of only 500 people worldwide trained by Brené Brown to facilitate Dare to Lead™ and is a Certified Enneagram Practitioner. Eileen coaches executives, facilitates yearlong women's leadership forums, and supports leaders in creating transformational shifts.
A recipient of the ATHENA Award, Golden Heart of Business Award, and named a Top 30 Businesswoman by Phoenix Business Journal, Eileen has served in board leadership roles for the Arizona Humane Society, The YMCA, Homeward Bound, Planned Parenthood of Arizona, and multiple chambers of commerce. She co-led US delegations to Uganda, Rwanda, Cambodia, Nepal, and South Africa through the Foundation for Global Leadership, and after a medical mission trip to Mali in 2009, she built a village school there. In 1998, she created a Baby Diaper Drive that became the Diaper Bank of Central Arizona.
Eileen is a committed lifelong learner and change agent who believes entrepreneurs don't retire – they evolve. With unbridled joy for life, she continues to travel internationally while coaching leaders who want to lead with courage, authenticity, and open hearts.
Connect with Eileen:
Resources Mentioned in This Episode:
Sam Chia spent 35 years in corporate leadership - VP roles, Fortune 500 companies, running regional businesses across Asia. He was successful by every traditional measure. Then he discovered coaching by accident.
While traveling 60-70% of the time as a regional VP, Sam noticed his team constantly queuing outside his office like patients at a clinic - waiting for him to solve their problems and approve their decisions. Frustrated by being a bottleneck, he learned coaching techniques to empower his team. The results were immediate: his team became more self-sufficient, learned faster, and stopped waiting for him to make every decision.
That experience planted a seed. But Sam didn't immediately jump into coaching. It took an acquisition that changed his organization's culture and leadership to make him realize: "In the corporate world, this is the kind of thing you have to face. Is there something I can be more in control of?"
The transition wasn't romantic. It was brutal.
Sam faced what he calls an "identity crisis" - going from having a Fortune 500 brand backing every conversation to being just "Sam." People who used to eagerly take his calls suddenly went cold. He went from high earner to zero income overnight. He had to learn functions he'd always delegated: marketing, sales, website building, funnel creation.
His first business model, running an HR consulting firm with 15 full-time consultants, taught him "the hard way" that overhead kills coaching businesses. So he pivoted to a solo model with a collaborative network of trusted coach partners.
Today, Sam runs a sustainable coaching practice that earns about 50% of his corporate income - but on his terms.
He works primarily with executives and emerging leaders in middle management and above, helping them navigate the challenging transition from individual contributor to people manager. His coaching engagements typically run 6-12 months, allowing him to see real transformation - not just training attendance.
In this episode, Sam shares:
This conversation is raw, honest, and packed with practical wisdom.
Sam doesn't sugarcoat the challenges of building a coaching business. He talks about trusting the wrong people who stole clients (who eventually came back). He discusses the cultural dynamics that make experience and shared background crucial in Asian coaching markets. He shares why some new managers discover they don't actually want to be leaders - and how that's still a successful coaching outcome.
If you're considering leaving corporate to become a coach, this episode is required listening. Sam provides a realistic roadmap that balances passion for helping people with the business fundamentals required to survive and thrive.
About Sam Chia: Sam is an ICF PCC-certified leadership coach with over 35 years of corporate leadership experience, including VP and MD roles across Fortune 500 companies, government agencies, and nonprofits. He holds an ACC, MBA, and has completed executive education at Harvard. Sam is co-author of two books on coaching in Asia and has been running his coaching practice in Singapore for over a decade.
Retry
In this episode of Coach as Entrepreneur, David sits down with Francis Strickland, a business strategist and coach who brings 30 years of global corporate HR leadership to small and mid-sized businesses. Now based in Switzerland after a remarkable career journey from South Carolina to Wisconsin and beyond, Francis shares powerful insights on what it truly means to build a coaching business with clarity and purpose.
Key Topics Covered:
- The shift from corporate coaching to entrepreneurship – How COVID-19 revealed the need for authentic leadership and sparked Francis's transition into professional coaching
- Authentic leadership vs. performative leadership – Why leaders must connect with their genuine selves rather than just executing mandates
- The harsh realities of scaling too fast – A cautionary tale about hiring corporate talent for a small business and the importance of values alignment
- What coaches really need before building a website – Why message clarity trumps professional branding in the early stages
- Selling safety, not services – How to communicate value in a way that builds trust with potential clients
- Vertical vs. horizontal development – The difference between skill-building and transformational mindset shifts for entrepreneurs
Francis offers candid advice for new coaches: get crystal clear on who you are and the impact you want to make before your first client conversation. She's currently building a community to provide straightforward, high-impact business foundations for coaches and entrepreneurs who need guidance beyond just coaching methodology.
This conversation is essential listening for any coach struggling with messaging, scaling decisions, or the transition from service provider to true business owner.
In this episode of Coach as Entrepreneur, David sits down with Mel Rosenthal—a Melbourne-based coach and mentor to founders and executives—about shifting from corporate leadership into purpose-driven coaching. Mel shares how informed curiosity, constant reflection, and simple systems create sustainable practices; why purpose can be a better north star than goals; and how relationships and reputation outcompete ads and funnels for long-term growth. We also dig into coaching the “whole person,” leading in technical environments, and building supportive peer rhythms so you don’t do this alone.
Show Notes:
Guest Bio
Mel Rosenthal is a coach, mentor, and writer based in Melbourne, Australia, who helps founders and executives navigate the messy challenges of growth and leadership. With over 4,500 coaching conversations and 15 years leading product, marketing, and innovation teams, she’s known for her “informed curiosity”—spotting patterns others miss, cutting through complexity, and challenging with care.
How to connect with Mel:
https://www.linkedin.com/in/rosenthalmelissa/
https://melissajrosenthal.com/
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