What actually happens to people after an acquisition closes? Anne-Marie Mills has lived it twice — first as HR lead when Algorithmia was acquired in 2021, and again in a more recent transition spanning teams from Seattle to Eastern Africa. In this episode, Anne-Marie walks through both experiences with real honesty: the early excitement, the culture shock six months in, the attrition nobody stopped, and what she wished leadership had done differently. If you work in people operations, run a team through any kind of organizational change, or have ever wondered why the talent you acquired seems to quietly disappear, this conversation is the post-mortem you didn't know you needed.

Frédéric Rivain is the CTO at Dashlane, a leading cybersecurity company — which means when AI coding tools started flooding the market, his team had more reasons to be skeptical than most. In this episode of Herding Squirrels, Frédéric walks us through how Dashlane built real AI adoption across an engineering org that had legitimate security concerns about the tools, why the hardest part of the rollout was never the technology, and what leaders get wrong when they treat AI adoption as a deployment problem instead of a people problem. If you’re leading a team through an AI transition right now, this conversation is the honest version of what that actually looks like from the inside.

What does it take to scale a fintech product from startup to flagship while keeping your team aligned and engaged? Gowri Sivaraman has spent 25+ years answering that question across multimillion-dollar products at companies like Intuit. In this episode, she shares the hard-won wisdom behind building teams that hold each other accountable and have fun doing it—revealing why the best teams never lose sight of their shared vision, how to remove emotion from cross-functional accountability, and what a failed basketball attempt taught her about leadership vulnerability.

In this episode, Barninder shares his counterintuitive approach to leading through uncertainty: upskilling your existing team beats hiring specialists every time. Your people already understand your culture, your technology, and your constraints—teach them the new skills rather than bringing in outsiders who'll spend months learning what your team already knows. He draws parallels between failed "Chief Digital Officers" and today's siloed "AI teams," warning that specialized groups without organizational integration create more problems than they solve.

In this episode, Boomie builds four LEGO models that reveal her philosophy on engineering leadership. From her personal life to the best and worst team experiences, she shares insights on clarity, alignment, and the balancing act CTOs face in today's rapidly changing tech landscape. The conversation dives deep into managing AI adoption, addressing fear at all organizational levels, and why transparency—balanced appropriately—is critical for team success.

In this conversation, Rosemary shares the story of successfully merging two engineering teams, navigating a high-stakes product launch under time pressure, and the leadership lessons learned from experiencing both her best and worst team experiences. Rosemary offers practical wisdom on building psychological safety, managing uncertainty during organizational change, and why "thrashing" - expending energy without direction - might be the biggest hidden threat to team effectiveness. Her insights on transparency, leveraging diverse perspectives, and using AI tools to challenge leadership blind spots provide a fresh perspective on modern engineering leadership.

You're caught between your team's needs and executive expectations—and you're wondering if there's a better way. Jossie Haines spent 25+ years leading engineering teams at Apple, Zynga, Tile, and American Express, and she's figured out what actually works. You'll hear about the three pillars that keep new leaders from drowning, why your engineers need to process change before moving forward, and what made one team gel so powerfully they built a social network in two weeks.

You're standing on uneven ground. Some days feel solid, other days you're balancing on smaller steps, wondering if you're doing the right thing. Your team is burning out. Deadlines are crushing. And somehow, you're supposed to care about people while shipping product. In this episode, Harini Rajagopal uses LEGO bricks to reveal what made her best team experience happen during COVID—when everything was falling apart. She builds the difference between micromanagement and trust, shows why "you don't have to be best every single time," and shares the leadership advice that turns three impossible options into thirty. If you're trying to balance time pressure with team care, wondering how to lead without all the answers, or navigating the constant tension between shipping and supporting, this conversation will give you permission to be human.

You’ve felt it before—that moment when your team just works. Everyone knows what they’re doing, has what they need, and you’re all moving in the same direction. But you’ve also experienced the opposite: the chaos, the misalignment, the daily fight for relevance. In this episode, Adam Tal uses LEGO bricks to build the difference between these two realities. Through hands-on models, Adam reveals what separates teams that thrive from teams that merely survive, why staying at an organization long enough to see the results of your decisions matters more than you think, and what new leaders need to know about supporting rather than directing their teams. If you’re navigating organizational change, leading through uncertainty, or wondering how to create stability in a fast-moving environment, this conversation is for you.

Oliver Gray, Director of Engineering at Trustpilot, shares his journey of transforming underperforming engineering teams into high-performing, self-directed powerhouses. Through hands-on LEGO models, Oliver reveals the power of bottom-up mission development, the pitfalls of fixed-price consulting projects, and why the best thing you can do as a leader is make your team stop needing you. From navigating AI adoption to creating psychological safety in hybrid environments, this conversation offers tactical wisdom for anyone leading technical teams through uncertainty.

In this engaging episode, Louie Celiberti, Managing Director and Head of Software Engineering at Guggenheim Partners, shares his insights on leadership through uncertainty, building cohesive teams, and navigating generational differences in the modern workplace. Through LEGO models, Louie demonstrates powerful concepts around servant leadership, embracing risk, and the cultural shifts happening in technology teams.

Nicole Tibaldi, Engineering Director at The New York Times, joins us to explore what makes teams truly exceptional. You'll discover why the "shortcuts" to psychological safety don't work, how to lead through uncertainty when there's no playbook, and Nicole's surprising take on what went wrong when leadership used project cancellation as a "test." This conversation reveals that the foundation of great teams isn't complex—it's about patience, transparency, and showing up consistently for your people.