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?
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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.