Not all bosses who feel "bad" are actually terrible people—sometimes they're just the wrong fit. But how do you know the difference? And more importantly, when does it stop mattering?

In this episode, Carl Oliveri gets brutally honest about navigating 4 company exits (including an IBM acquisition that went from startup culture to 15 bosses overnight), why vulnerability is the most underrated leadership skill, and what he learned from the bosses he couldn't stand working for.

This is part 2 of our 3-part series exploring the messy, uncomfortable truths about leadership that nobody talks about on LinkedIn.

You'll hear about: 

• The real story behind company exits (they're not all wins)

• Managing culture through private equity transitions

• Why leading with vulnerability earns trust when pressure is high

• How to shield your team from stress without killing performance • What bad bosses actually teach you about the leader you want to be

This episode supports the FaceIT Foundation—peer support for men's depression recovery and breaking down mental health stigma.

In this conversation, Ken Roden and Carl Oliveri explore the journey of self-discovery, the importance of vulnerability in leadership, and the impact of personal experiences on professional growth. Carl shares his insights on how introverts can excel in sales, the significance of helping others succeed, and the lessons learned from both personal and professional challenges. The discussion emphasizes the need for authenticity, empathy, and the courage to pursue fulfillment in one's career.

This week we are supporting the Face It Foundation, a newer organization doing peer support for men's depression recovery and breaking down the stigma around men seeking help

Takeaways

• Ken identifies as an extrovert but feels shy in big groups.
• Carl's journey in sales began with a misunderstanding of the role.
• True leadership is about listening and helping others succeed.
• Vulnerability is essential for building trust in leadership.
• Finding fulfillment in work is crucial for personal happiness.
• It's important to be honest with oneself and others.
• Success can lead to an inflated ego and personal challenges.
• Personal experiences can significantly impact professional life.
• Co-parenting can lead to better relationships post-divorce.
• Empathy in leadership can enhance team performance.

• The Journey of Self-Discovery in Leadership
• Vulnerability: The Heart of Effective Leadership

• "Don't sit in the room, don't waste your time."
• "You can build a lot of trust with people."
• "Success bred a whole lot of cockiness."

What happens when you ask a successful leader how they really got where they are? 

Shana Glenzer, VP of Marketing at Oleria and DC tech fixture for over two decades, shares the unfiltered truth about her career journey—including the moments that don't make it onto LinkedIn.

In this premiere episode of "What We Don't Say," host Ken Roden (doctoral researcher in workplace evolution) sits down with Shana to uncover the real story behind her rise in DC's competitive tech scene. From their days working together at Blackboard 15 years ago to her current role leading marketing strategy, Shana reveals the messy, thoughtful, and sometimes surprising moments that shaped her leadership approach.

Plus: How being a mother to three boys, including one with cerebral palsy, fundamentally changed her perspective on leadership—in ways you probably wouldn't expect.

This Week's Featured Charity: Cerebral Palsy Foundation - Supporting research, care programs, and community initiatives for individuals with cerebral palsy.