Herding Squirrels Ep 11
w Nicole Tibaldi
Engineering Director, New York Times
Herding Squirrels: Building Trust Through Transparency with Nicole Tibaldi
Episode Overview
Nicole Tibaldi, Engineering Director at The New York Times, joins us to explore what makes teams truly exceptional. Through LEGO builds that visualize team dynamics, Nicole shares powerful insights from her decade-plus experience leading teams at CircleCI, Gatsby, and now the Times. 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.
Key Timestamps & Highlights
[1:45] - Best Team Experience: Nicole builds a model showing clear roles (different colored pillars) connected by bridges, representing team members who could "cross functions" - engineers who understood design, designers who understood engineering. The rotating center piece shows the fluidity this created.
[3:04] - Nightmare Team: The obstacle course model representing being "tested" by leadership, with a wall between the team and the actual company goal. Nicole reveals leadership once fake-canceled a project just to see how the team would react.
[7:01] - Leading Through Uncertainty: Nicole's model features diverse shapes for "trying new things," eyes for listening to the team, transparent pieces for reflection, and guardrails representing core leadership principles. She emphasizes there are no shortcuts to psychological safety.
[13:17] - Leadership Guardrails: The two most important ones - transparency (sharing as much as possible) and curiosity (remembering there's no one right answer). "Nobody wants an unpredictable manager" - consistency in how you show up matters.
[15:57] - AI in the Workplace: Nicole's nuanced view - use AI to remove drudgery (writing tests, documentation, JIRA tickets) but be careful not to remove the "aha moments" that give engineers satisfaction in their work. Emphasizes measuring impact rather than assuming benefits.
[17:03] - Advice for New Leaders: Nicole's final build shows the importance of understanding context ("all the different varied things that happened before you were there") and having patience for the climb to build trust and healthy teams.
Memorable Quotes
"Nobody wants an unpredictable manager. If somebody's coming to you with a problem, they want to have a sense of how you're going to react."
"The route to psychological safety is a long one, but it's definitely worth the journey."
"Everything worked like this [on my best team], so that's the model I have to set everything up like... as it turns out, that's not how that works."
"We don't know where we want to plant the flag. So we've got to be always looking up and ready... Have lots of resources... and keep your options open."
"If nobody has a vision of the goal, they can't make decisions. They'll either make decisions where they don't have enough information or they'll constantly have to come looking for answers. Neither of those things are good."
Where to Find Nicole
Connect with Nicole Tibaldi on LinkedIn
Recorded in NYC
Herding Squirrels is a podcast about modern teams, where we uncover the nuts and bolts of what makes teams work. Each episode features guests building their thoughts and ideas with LEGO bricks, creating a unique conversation about leadership, collaboration, and team dynamics.
