I sit down with executive coach Jen Wilson to explore how trust is rebuilt in teams, why leaders struggle to follow through on change, and how to realign before burnout forces you to.
Why Smart Leaders Know What to Change But Still Don’t Do It
In this episode, I have a deeply honest conversation with executive coach Jen Wilson about why meaningful organizational change starts with the internal work most leaders avoid, and how trust inside teams is built through shared commitment, not strategic planning alone.
We explore how trust is actually rebuilt during organizational disruption, and why so many leaders struggle to follow through even when they know exactly what needs to change. Jen breaks down the fears that derail decision-making: fear of failure, fear of visibility, and those relentless 3 a.m. thoughts that surface when the pressure of leadership feels overwhelming.
We also examine how seemingly practical structures like meeting formats either strengthen trust or quietly erode it, and why alignment with core values is essential for sustainable growth. Jen shares her own pivot point—that moment she returned home late one night, exhausted and empty despite her professional success, realizing her life was completely misaligned with her true values.
This conversation digs into how to recognize the signs of misalignment before they become a crisis, how to listen to your intuition (especially for women in leadership), and how to take practical steps toward realignment without needing a dramatic breakdown to justify the change. Jen emphasizes that transformation doesn’t require drastic action. Instead, she advocates for small, incremental shifts that can lead to significant change—like her experience of simply visiting a different coffee shop, which opened her eyes to her own preferences and desires.
We talk about navigating change without burning out, scaling organizations without losing yourself, and making meaningful personal and professional shifts when you’re standing at a crossroads. Jen also addresses how leadership must evolve to meet the expectations of Gen Z and the generations that follow, and why creating a common language makes honest, courageous conversations possible within teams.
This episode is for executives, entrepreneurs, therapists, coaches, and anyone who feels quietly misaligned, sensing that something needs to change but unsure where to start. Jen offers a free values workbook to help you clarify what you truly stand for, and we discuss the questions that reveal whether you’re living in accordance with your core values: “What do I know to be true right now?” and “Am I living according to what matters most?”
The journey of transformation begins with recognizing the need for change and being willing to embrace discomfort. This conversation reminds us that listening to our intuition and aligning our actions with our values are essential steps toward personal and professional fulfillment. By asking the right questions and taking small steps, we can navigate our own pivot points and create a more authentic, satisfying life.
