What happens when your highest performer becomes your biggest people problem?

In this episode of Let’s Think About This, Jeff Jacobs joins Benicia Stein and Milly Pineda to tackle a messy workplace reality: an employee who delivers incredible results… but snaps in meetings, challenges leadership publicly, and creates tension across the team.

At what point does “high performance” stop being high performance?

The conversation digs into the WHAT vs. the HOW of performance, why leaders can accidentally normalize bad behavior, and what it really takes to reset expectations without destroying trust.

We’re talking emotional maturity, accountability, difficult conversations, the power of the pause, and why consistency matters long after the uncomfortable conversation is over.

Because sometimes the question isn’t just, “How do we fix this employee?”

It’s “What has leadership been allowing?”

If you lead people, work on a team, or have ever watched someone get away with behavior because they’re “too valuable,” this one is for you.

Email us at [email protected] to tell us what YOU would do in this situation!

Subscribe for more real conversations about the situations nobody gives you a handbook for.

If you manage people, work on a team with uneven effort, or have ever wondered whether flexibility is being mistaken for laziness, this conversation will hit home. It’s an honest, practical look at how leaders can keep performance high without losing the human beings doing the work.

Join Benicia Stein, Milly Pineda and special guest Colette Stein as they discuss a stressed-out Gen Z team member, three high-performing coworkers, and a leader stuck in the middle - this episode gets into the messy reality of work-life balance, accountability, and what happens when a team starts quietly resenting each other.

Have a situation you think we should unpack? A workplace dynamic you can’t stop thinking about? Or a topic you’d love to hear brought to the table? Send it our way at [email protected]. Your story or idea could inspire a future conversation.

Be sure to like, subscribe, and tune in next week for another conversation worth thinking about.

Until then, let’s think about this.

Episode #3 of Let's Think About This IS HERE! On this episode we feature special guest Rachel Ingel Champion and discuss intentional leadership, self-awareness and more!

Chapters

• 00:00 Feedback and Intentional Leadership
• 23:28 Leading Neurodivergent Teams
• 24:10 Different Approaches to Work
• 25:32 Managing Neurodivergent People
• 26:21 Self-Awareness and Reflection
• 27:26 Lived Experience and Bias
• 28:08 Intent vs. Impact
• 29:30 Leadership of Self
• 30:32 Feedback and Perception
• 31:27 Authenticity in the Workplace
• 32:08 Behavior and Intention
• 33:01 Leading with Intention
• 34:12 Self-Reflection and Communication
• 35:26 Understanding Different Leadership Styles
• 36:18 Championing Authenticity
• 37:39 Impact of Champions in the Workplace
• 39:36 Agency and Leadership
• 42:03 Buffering Dominant Cultures
• 43:03 Continuous Self-Awareness

What happens when someone is exceptional at their job, but the way others perceive them starts putting a cap on their potential?

In Episode 3, “The Perception Cap,” Let’s Think About This explores a leadership scenario that challenges us to look beyond performance and examine the human side of leading. From neurodiversity and lived experiences to psychological safety, intentional feedback, and self-awareness, we unpack how perception can shape who gets seen as a leader and who gets overlooked.

Because great leadership isn’t about fitting one mold. It’s about staying curious, leading with compassion, and creating space for different kinds of leaders to thrive.

Let’s Think About This | Episode 3: The Perception Cap
Available on YouTube, Spotify & Apple Podcasts

Chapters

• 00:00 The Scenario and Self-Awareness
• 04:23 Leadership Facilitation and Psychological Safety
• 16:13 Intentional Feedback and Development Objectives
• 23:28 Leadership and Neurodiversity
• 24:10 Self-Awareness and Leadership
• 27:26 Lived Experience and Leadership
• 40:25 Agency and Leadership

What happens when a leader walks into the room with an idea they believe in—only to have it dismissed before it ever gets a real chance?

In Episode 2 of Let’s Think About This, Benicia Stein is joined by Milly Pineda and Akbar Sultan to unpack a real-life leadership scenario that opens the door to a much bigger conversation: navigating leadership in male-dominated spaces, building trust and influence at the executive level, and knowing how to respond when your voice—or your expertise—is dismissed.

Together, they explore the importance of doing the relationship-building work before entering the room, creating psychological safety within leadership teams, and investing intentionally in coaching and professional development. They also discuss self-belief, authentic executive presence, the power of the pause, and what it takes to keep one difficult moment from becoming your final attempt.

Because sometimes leadership means finding the courage to try again—and sometimes it means recognizing when it’s time to choose a different table.

Let’s Think About This isn’t a panel of people claiming to have all the answers. It’s three leadership professionals with different experiences and perspectives thinking through the situations leaders actually face—and inviting you into the conversation.

Featuring: Benicia Stein, Milly Pineda & Akbar Sultan

Have a leadership scenario you want us to think about?
Contact us at [email protected]

Chapters

• 00:00 Leadership Challenges in Male-Dominated Spaces
• 11:31 Building Relationships and Trust at the Executive Level
• 25:18 The Power of Self-Belief and Authentic Professional Presence
• 30:45 Choosing a Different Table if Respect is Not Served

Welcome to the very first episode of Let’s Think About This — Proof of Concept, featuring special guest Kendra Dahlstrom.

This first conversation puts the idea behind Let’s Think About This into action: bringing experienced voices together for real, unscripted conversations about leadership, the challenges that come with it, and the perspectives we don’t always hear.

No perfect answers. No leadership clichés. Just honest experiences, thoughtful questions, different perspectives, and conversations worth having.

This is Proof of Concept.

Listen in, challenge your thinking, and let’s think about this.

Have a question, topic, or idea you’d like us to explore? We’d love to hear from you. Email us at [email protected].

Let’s Think About This is a New Kind of Leader production.