Let’s Think About This is a show where leadership professionals and leaders come together to unpack real leadership situations happening right now.
In each episode, Benicia Stein and Milly Pineda bring a real-world leadership challenge and a new voice into the room. We debrief what’s happening, share our hot takes, challenge our own thinking, explore what the leader could consider, and talk through what they might do next.
Some of the best leadership learning happens when we’re willing to talk openly about what’s actually happening: the decisions, dynamics, tensions, and possibilities. The conversations behind the conversations. But not everyone gets access to those conversations.
So, we invite you to join us, listen in, and learn with us.
Let’s Think About This brings you into the room. No perfect answers. No easy playbooks. Just real leadership situations, different perspectives, and the opportunity to think together.
We believe learning from others’ lived experiences fuels growth.
Let's Think About This - Turning Harsh Criticism Into Growth
In this episode, we’re doing things a little differently. No guest. No questions. Just Benicia and Milly getting real about moments in their careers that didn’t go quite how they expected.
Milly shares what happened when a senior leader’s harsh feedback took the excitement out of a major accomplishment. Benicia opens up about being laid off just two weeks after a big career moment.
So what do you do when someone else’s words knock the wind out of you?
Do you take it personally? Brush it off? Or is there something worth learning?
We’re talking about criticism, tough conversations, and learning not to let someone else’s opinion become your reality.
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 letsthinkaboutthis.show@gmail.com (mailto:letsthinkaboutthis.show@gmail.com). 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.
26 Sept 2026
Let's Think About This - Performance Isn't Everything
If you’ve ever struggled with a high performer’s behavior - or wondered how to give feedback without making things worse? This conversation is for you!
In this episode, Benicia, Milly and special guest Claire Davis unpack a complicated workplace dynamic and explore how leaders can separate intent from impact, address difficult behavior, and build teams where accountability and respect go hand in hand.
Do you have a workplace scenario you want us to unpack next? Send your submissions to: letsthinkaboutthis.show@gmail.com (mailto:letsthinkaboutthis.show@gmail.com)
Please like and subscribe for more episodes like this one!
19 Sept 2026
Let's Think About This - Lead With Compassion
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 letsthinkaboutthis.show@gmail.com (mailto:letsthinkaboutthis.show@gmail.com) to tell us what YOU would do in this situation!
Subscribe for more real conversations about the situations nobody gives you a handbook for.
11 Sept 2026
Let's Think About This - The Generational Divide
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 letsthinkaboutthis.show@gmail.com (mailto:letsthinkaboutthis.show@gmail.com). 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.
15 Aug 2026
Let's Think About This - A Seat at the Table
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 letsthinkaboutthis.show@gmail.com (mailto:letsthinkaboutthis.show@gmail.com)
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
8 Aug 2026
Let's Think About This - Lead With Trust
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 letsthinkaboutthis.show@gmail.com (mailto:letsthinkaboutthis.show@gmail.com).
Let’s Think About This is a New Kind of Leader production.
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