
Insights

Herding Squirrels Ep 14
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.

Herding Squirrels Ep 13
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.

Herding Squirrels Ep 12
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.

Herding Squirrels Ep 11
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.

Herding Squirrels Ep 10
When Your "Band of Misfits" Becomes an Engineering Powerhouse
Your most unconventional team member might be your secret weapon. Your weirdest hire could drive your biggest breakthrough. Ready to stop building cookie-cutter teams?
This week on Herding Squirrels, Val Akkapeddi (Director of Engineering at Collectors) builds some eye-opening models about why the quirkiest teams often deliver the most extraordinary results.

Herding Squirrels Ep 09
This week on Herding Squirrels, Ilya Lazebnik (Director of Infrastructure at Placer.ai) built some eye-opening models about what it's really like leading distributed teams across continents and generations.
What You'll Discover:
The "Show Me" Leadership Revolution - Why saying "just show me" cuts through more communication BS than a dozen Zoom calls ever could
The Multi-Dimensional Team Nightmare - Managing Gen Z developers, international time zones, and cultural differences simultaneously (spoiler: it's as messy as it sounds)
AI as Your Communication Translator - How smart leaders are already using AI to decode whether that Slack message was passive-aggressive or just poorly written

Herding Squirrels Ep 08
I sat down with Allison McHenry (CTO at Daily Kos, formerly NYT, Meta, Daily Beast) for a conversation about leading through uncertainty—and she dropped some serious wisdom about career paths.

Herding Squirrels Ep 07
In this engaging episode, we explore leadership through the lens of technical teams with Dave Walters, former CTO of Hired, Lacalle Group, and Spa Finder Wellness. With 13+ years at The Knot Worldwide (XO Group) and 20+ years as a volunteer firefighter, Dave brings unique perspectives on leading high-stakes teams. Using LEGO® Serious Play® methodology, Dave shares powerful insights on team alignment, staying calm under pressure, and nurturing collective success.

Herding Squirrels Ep 06
In this engaging episode, we explore leadership through the lens of trust and vulnerability with John Fly, CTO of FirmPilot. Using LEGO® Serious Play® methodology, John shares powerful stories from his 25+ years in technology leadership, revealing how his approach evolved from technical perfectionism to collaborative partnership.

Herding Squirrels Ep 04
Join us as we play with Frédéric Rivain, CTO of Dashlane, as he shares insights on building high-performing technical teams through LEGO® Serious Play® methodology. Discover why team "intimacy" and intentional relationship-building are crucial for engineering leadership, how to avoid the dangerous trap of "illusion of alignment," and practical strategies for navigating remote work challenges. From unity and consistency to stepping outside your network, learn actionable advice for technical leaders at every career stage

Herding Squirrels Ep 05
Join host Brandon Wetzstein as he welcomes Jessica Mosley, a quality engineering veteran with over 20 years of experience spanning software development, DevOps, IT, and customer experience. Through innovative LEGO® Serious Play® methodology, Jessica shares valuable insights on team building, leadership development, and creating authentic workplace connections in today's distributed work environment.

Herding Squirrels Ep 03
In this enlightening episode of Herding Squirrels, host Brandon Wetzstein sits down with Cole Christie, Senior Engineering Manager for Site Reliability Engineering at Gap. With 18 years of experience in tech and 10 years in leadership positions, Cole shares profound insights about team dynamics across various industries.