Most managers are so focused on getting the work done, they never stop to ask: are we actually leaving room to do it well?

In this episode, I sit down with Reid — engineering manager, deeply well-read, and someone who introduced me to a concept I now can't stop thinking about: organizational slack. Not the chat app. The breathing room that separates a team that can think, create, and adapt from one that's just grinding toward collapse.

We get into why micromanagement is usually fear dressed up as accountability, the difference between being a manager and actually leading a team, and what Rasmussen's Drift model tells us about what happens when there's no buffer left in the system. We also talk motivation — why assuming your team is driven by the same things you are is one of the most common and costly mistakes a leader makes.

Plus: the case for being delusional, and why being a slacker might be the most underrated leadership skill of our time.

Learning to Disagree Without Being Disagreeable

Every leader has said it: "I have an open door. Bring me your concerns." And then... nothing. No one comes. And yet somehow everybody's talking to everybody except the person they actually have an issue with. In this episode, I sit down with Danielle Loevy a mediator, executive coach, and former employment lawyer. We dig into why disagreement is a skill most of us prefer not to engage, why calling yourself "conflict avoidant" is a limiting label, and what's really happening when your team won't just talk to each other. Plus, she provides four pillars for actually getting good at disagreement. And yes, a foster dog makes a cameo.

Have you ever watched a murmuration of starlings? Thousands of birds, no leader, no plan — moving like one organism. That's not magic. That's emergence. And it's exactly what's happening on your team, whether you're paying attention or not.

This episode is about the invisible architecture of teams — the dynamics that form whether you design them or not. I walk through three layers of how team behavior actually develops, pull from Adrienne Maree Brown's Emergent Strategy, and revisit Kurt Lewin's counterintuitive finding: it's easier to change a group than to change an individual.

I tell two stories that made this real for me. The first: I went to a retreat, had a genuine transformation, came home — and my environment hadn't changed. The environment won. The second: I sat on a board where the defining norm was harmony. Don't disagree with the inner circle. I abstained from one vote. That was enough to break it.

Norms aren't rules. Nobody writes them down. But they run everything.

Most of us have been on teams our whole lives — sports teams, school projects, work groups — and still have no idea what a team actually is. Spoiler: most of what we call "teams" aren't. In this episode, I'm breaking down the difference between a working group and a real team, why interdependence is the thing that changes everything, and what researchers like Richard Hackman and Amy Edmondson actually mean when they talk about "teaming." It's more useful — and more unsettling — than the motivational poster version.

I also get honest about something personal: I grew up on sports teams and was sometimes a genuinely terrible teammate. Not because I didn't care — because I cared too much about the wrong things. If you've ever wondered why some groups click and others just... coexist — this one's for you

Connect:

https://www.linkedin.com/in/jessy-grossman/

@coachjessygrossman

zlncoaching.com

In this episode, Jessy Grossman and Amanda Hoffmann dive deep into the meaning of clarity — not as certainty or perfection, but as an ongoing practice of understanding, alignment, and curiosity.

Amanda shares her Core Alignment Model, a framework designed to help people reconnect with their identity, values, and aspirations—and to interrupt the growing epidemic of the borrowed self: the version of ourselves we adopt from others' expectations.

Rich, reflective, and refreshingly honest, this conversation will help you pause, notice, and reconnect. Learn more about Amanda Hoffmann's work: https://www.linkedin.com/in/arhoffmann/

In this conversation, Katerina and Jessy explore the shiny, new ideas shaping the future of organizations—namely decentralization, democratized decision-making, and transparent information flow. Drawing on Katerina’s experience working inside emerging organizational structures and teaching on new technologies, they translate concepts from Web3, DAOs, and network-based leadership into practical lessons for leaders working in traditional companies today.

Together, they unpack why information sharing is becoming one of the most critical leadership skills, the strengths and limits of decentralized structures, and what corporate America can adopt (without needing a blockchain or token system). The conversation highlights the evolving role of leaders—not as answer-givers, but as connection-builders who create the conditions for people to collaborate, communicate, and make better decisions together.

As more organizations operate in complex, fast-changing environments, leaders are increasingly expected to orchestrate networks, not manage silos. This episode bridges the world of emerging organizational tech with real-world leadership challenges—and gives listeners practical ways to experiment with decentralized principles in their own teams.Learn more about Katerina: https://www.linkedin.com/in/katerinabc/

What story are you telling about who you are—and who you’re becoming?

In this episode, Jessy Grossman sits down with Professor Dan P. McAdams, one of the world’s leading experts and field-defining scholars on narrative identity and personality development. Professor McAdams — the Henry Wade Rogers Professor at Northwestern University — has spent his career studying how we weave our experiences into stories that give our lives coherence, meaning, and purpose.

Together, they explore how the stories we tell about ourselves shape the way we lead, adapt, and ultimately leave a legacy — especially during times of uncertainty and change.

If you enjoy this episode, don’t forget to subscribe to Too Millennial and leave a review — it helps us reach more leaders like you!

Learn more about Dan McAdams’ work on narrative identity: https://sites.northwestern.edu/studyoflivesresearchgroup/

Join Karrie Sullivan, founder of Culminate Strategy Group, as she delves into the intricacies of AI adoption and organizational transformation. In this conversation, we explore why understanding the human element is key to successful change — and how leaders can meet people where they are, shift mindsets, and show up with confidence through uncertainty.

Let’s stay connected!

Follow me on Instagram @CoachJessyGrossman for leadership insights, behind-the-scenes stories, and tools to help you grow as a leader.

Connect with me on LinkedIn, and connect with Karrie Sullivan to continue the conversation on AI adoption and organizational transformation.