Ep 103, Why Leaders Fail: The Blind Spots That Sabotage Success

Do you ever think, “Why do I keep doing this?” You know it’s not working, but you’re stuck on autopilot. Here’s the truth: most leaders don’t fail because of lack of skill or knowledge. They get derailed by lack of self-awareness. In this episode, Jenn shares a story of how laughter in the wrong moment nearly sabotaged her leadership, and what it took to see the blind spot. You’ll discover why self-awareness isn’t about beating yourself up but about ruthless honesty and radical compassion. Plus, how the Enneagram helps reveal the hidden motivations that keep you repeating patterns you can’t see. Because without self-awareness, trust unravels, communication falters, and joy erodes. But when you uncover your blind spots, you can lead with clarity and choose joy on purpose.

Here’s What’s in the Episode

2:09 The feedback that changed Jenn’s leadership.
05:11 The surprising research on how few leaders are truly self-aware.
07:15 Why your personality can, “drive the bus” if you’re not paying attention.
08:49 How the Enneagram reveals your hidden motivations and blind spots.
13:45 The difference between using personality tools for growth versus excuses.
14:48 A free resource to start uncovering your motivations: Why Do I Keep Doing This?

Key Takeaway

Self-awareness in leadership is the #1 predictor of success, and the Enneagram helps uncover blind spots that sabotage communication and culture.

About the Host: Jenn Whitmer

Jenn is an international keynote speaker, leadership consultant, and the founder of Joyosity™, helping leaders create positive, profitable cultures through connection, curiosity, and joy. With a background in communication, conflict resolution, and team dynamics, Jenn helps leaders and organizations navigate complex people challenges, reduce burnout, and build flourishing workplaces. Her insights have resonated with audiences worldwide, blending real-world leadership expertise, engaging storytelling, and a dash of humor to make the hard stuff easier. Whether on stage, in workshops, or with coaching clients, Jenn equips leaders with the tools they need to solve conflict, cultivate communication, and lead with purpose. Her upcoming book Joyosity hits shelves fall 2025, offering leaders a fresh approach to joy at work that builds real results.

Resources & Links:

Preorder Joyosity:

Joyosity: How to Cultivate Intense Happiness in Work & Life (Even If Things Are What They Are) Joy isn’t fluff — it’s fierce strategy. This book gives leaders the tools to turn exhaustion into resilience and build cultures where work is a joy, people are whole, and organizations flourish.

Free 99 Steps:

Why Do I Keep Doing This? Enneagram Motivations → A quick guide to the five motivations that drive your quirks — and how to flip the script.

Ready to Make a Plan:

Joyosity™ Jumpstart → Get crystal clear on what you want, what’s in the way, and how to move forward with traction.

Starting the Journey:

Enneagram Navigator → Stop guessing your type. In this 1:1 session, get clarity on your motivations and blind spots.

Ready to Dive In:

Joyosity™ Intensive → A one-day transformative experience to realign with your values and build a practical plan for joyful leadership.

A Party for More:

Bring Jenn & the Joy to Speak → Bring the spark (not just the spark notes!) to your whole team with contagious joy, practical tools, and plenty of laughter.

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