Jack Glennon is the founder of Glennon Peak Coaching and a seasoned leadership coach with over 20 years of experience in senior leadership roles across diverse industries. His expertise lies in empowering professionals to navigate difficult career transitions, recover from workplace adversity, and rebuild with clarity and resilience. Jack has a unique ability to help people redefine their identity after challenges such as toxic “family” business cultures, redundancies, or professional setbacks, offering strategies that foster authentic leadership and emotional intelligence. At the core of his work is a mission to help individuals thrive in their careers without sacrificing their well-being. Jack equips leaders to create healthier workplace environments that inspire empowerment, authenticity, and growth. His lived experience and professional insight make him a trusted guide for anyone seeking to transform workplace adversity into a foundation for lasting personal and professional success.

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Have you ever worked in a company that claimed to be a “family,” but instead left you feeling drained, unappreciated, or stuck?

In this episode of Talking with the Experts, I sit down with leadership coach Jack Glennon to unpack the truth about toxic “family” cultures in business. While these environments may look supportive on the surface, they often stifle personal growth, silence individuality, and take a heavy toll on well-being.

With over two decades of leadership experience, Jack brings both professional expertise and lived experience to this important discussion. He explains how toxic cultures can impact not just careers, but also physical and mental health. More importantly, he offers practical strategies for breaking free, rebuilding confidence, and redefining professional identity after adversity such as redundancy or unhealthy work dynamics.

Jack also speaks directly to leaders, showing them how to shift from controlling, stifling cultures to authentic, empowering ones. He outlines how leaders can foster environments that celebrate individuality, build resilience, and promote well-being across the team.

If you’ve ever wondered whether your workplace culture is lifting you up—or holding you back—this episode will give you the clarity and tools you need. Tune in to learn how to break free from harmful patterns and create a healthier, more authentic professional path.

📌 Key Takeaways

1. The impact of toxic “family” cultures on career growth and well-being.
2. How to redefine your professional identity after setbacks.
3. Leadership strategies for building empowering and authentic workplace cultures.

• Family culture becomes dangerous when employees work more than they should and sacrifice personal relationships because they buy into the family narrative, blurring professional boundaries.
• Business decisions like redundancies, layoffs, and disciplinaries can cause severe mental damage to employees who believed they were part of a company family, leading to years of bitterness and unresolved emotional trauma.
• Organizations with toxic family cultures often have CEOs who treat employees badly while maintaining the family rhetoric, creating environments where people either become part of the problem or leave.
• Practical strategies for redefining workplace identity after adversity include changing perspective by analyzing whether it was the person or the role that was eliminated, recognizing job loss as a chapter ending rather than the end of one’s story.
• Control is a key element that feels lost during workplace adversity, so shifting perspective from “this is happening to me” to “this is happening for me” helps regain that sense of control.
• Rose Davidson shared her experience leaving a law enforcement agency job where she had planned to become collector of customs, but the role had become so tied to her identity that leaving caused depression and mental breakdown.
• Jack recommends using redundancy payouts strategically by putting the lump sum into savings and creating monthly direct debits to effectively buy time for proper career transition planning.
• Healthier workplace cultures should eliminate family language and focus on authentic behaviors from leadership, including proper communication, valuing employees, and providing development opportunities.
• Culture cannot be forced through mandatory events or pizza Fridays, but must be built through genuine leadership behaviors that value people’s time, wages, and growth opportunities.
• Annual leave policies demonstrate authentic culture, where some companies automatically approve earned leave while others require employees to justify why they deserve time off during busy periods.
• Jack offers a free 30-minute introduction coaching session to address the coaching industry’s reputation problems and allow potential clients to determine compatibility without pressure.
• Coaching relationships require personal connection and trust, so the free session allows both parties to assess fit without guarantees of fixed timelines, as individual needs vary significantly.
• Setbacks don’t define people but refine them, and individuals should get comfortable dancing in the rain rather than fearing storms, as resilience comes from bouncing back through adversity.

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