Herding Squirrels

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

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.

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.

What You'll Discover:

The Don Quixote Leadership Philosophy - Why chasing your own windmills (even when others think you're crazy) leads to innovation that actually matters

The Biometric Backend Miracle - How a team of "adjacent skills" rebuilt an entire system in one month by becoming each other's confidence boost instead of competing for credit

The Scaling Leadership Trap - Why brilliant individual contributors crash and burn when they can't flip from "I have all the answers" to "let the team find their way"

The Tower vs. Glue Paradox - How career advice focused on "building your tower higher" is killing team performance (and what to do instead)

Plus, Val spontaneously builds the most revealing model we've ever seen about workplace culture—showing exactly why individual advancement destroys collective success.

The bottom line? Your best teams aren't the most qualified ones. They're the ones weird enough to try something different and connected enough to lift each other up while doing it.

Watch Val transform abstract leadership concepts into tangible insights, including the moment they literally flip their advice model upside down to show what real leadership looks like.

Episode Timeline

[00:00:00] - Introduction to Herding Squirrels podcast and guest Val Akkapeddi, Director of Engineering at Collectors

[00:00:36] - First LEGO build: Val creates a Don Quixote-inspired model with lance, representing their love for "tilting at windmills"

[00:02:53] - Discussion of Val's philosophy: chase your own vision regardless of whether others see it, find your windmill and pursue it

[00:03:38] - Second LEGO build: Val's best team experience - the "B Team" at Clear with diverse skill sets connected by strong culture

[00:05:17] - Story of rebuilding an entire biometric backend in one month through unconventional team composition and mutual support

[00:07:00] - Analysis of how "glue contributors" and culture made a "band of misfits" into an engineering powerhouse

[00:09:44] - Exploration of why being quirky, unbalanced, and non-standard drives innovation and different outcomes

[00:11:48] - Third LEGO build: Val's worst team experience showing a scaling failure with single-point-of-control leadership

[00:13:00] - Discussion of how brilliant leaders can fail when they can't let go of control as teams scale

[00:15:07] - Deep dive into letting teams "evolve as a glorious mess" and the challenge of releasing control

[00:18:52] - Analysis of the most destructive workplace dynamic: individual tower-building vs. lifting each other up

[00:20:00] - Val spontaneously builds a model contrasting selfish career advancement with collaborative team support

[00:22:06] - Final LEGO build: Val's advice for new technical leaders, flipping from individual expert to team connector

[00:24:12] - Val's reflection on building with LEGO as a way to make abstract thoughts concrete and touchable

Key Themes Explored

Tilting at Windmills: The power of pursuing your unique vision even when others don't understand or see it

Culture as Foundation: How strong team culture enables diverse, unconventional teams to achieve extraordinary results

Scaling Leadership Crisis: Why brilliant individual contributors often fail as leaders when they can't release control

Glorious Mess Philosophy: Embracing organized chaos and letting teams evolve their own structures and approaches

Individual vs. Team Success: The toxic dynamic of building personal towers vs. lifting the entire team up

Innovation Through Quirkiness: How non-standard approaches and "bands of misfits" drive breakthrough results

Notable Quotes

"Find your windmill and chase it... The only thing that's going to make you happy is something that comes from you."

"Culture really is the thing that makes a team work. The technology that you use, the tools, the processes, all of those can evolve. Culture and the team, being invested in each other's success and uplifting everybody's contributions—if you can get that story right, everything else falls into place."

"Let it evolve as a glorious mess... Let the team find their own structure."

"Don't be invested in people doing things the way that you would have done... Show them the problem, let them figure it out and let them tell you what the problem is that they should be solving."

"Find a way to become the glue and bring others to the table to let their contribution shine."

About the Guest

Val Akkapeddi is currently the Director of Engineering at Collectors, leading high-performing engineering teams. They believe in building culture as the foundation of strong teams and enjoy being a hands-on contributor to driving ambitious technical vision. Val is passionate about security research, gaming, running D&D campaigns, and finding unconventional approaches to complex problems.

Find Val on LinkedIn.

About Herding Squirrels

Herding Squirrels is a podcast about modern teams, hosted by Brandon Wetzstein. Through LEGO® Serious Play® methodology and engaging conversations, the podcast explores the nuances of effective teamwork, leadership, and collaboration in today's evolving workplace.

Ilia Lazebnik is the Director of Infrastructure at Placer.ai, where he leads the engineering teams behind their large-scale cloud systems. With over a decade of experience in DevOps, cloud architecture, and automation, Ilia is known for driving innovation, building robust infrastructure, and championing modern engineering practices. He’s a HashiCorp contributor and a passionate advocate for open source and tech community knowledge-sharing.

For more Ilia:

Linkedin

Github

Episode Timeline

[00:00:00] - Introduction to Herding Squirrels podcast and guest Ilya Lazebnik, Director of Infrastructure at Placer.ai

[00:00:46] - First LEGO build: Ilya creates a model with chef's hat and flag representing his passion for food exploration in NYC

[00:01:21] - Second LEGO build: Ilya's best team experience featuring creative freedom with guardrails and protective boundaries

[00:02:45] - Discussion of balancing creativity with structure and the importance of having both autonomy and direction

[00:04:37] - Third LEGO build: Ilya's worst team experience showing vulnerable exposure with "eyes watching" and lack of protection

[00:06:22] - Exploration of imposter syndrome, junior developer challenges, and the gap between perception and reality

[00:07:29] - Ilya's leadership approach: using "show me" rather than just verbal communication to bridge understanding gaps

[00:09:31] - Discussion of how remote work and pandemic changes have transformed team dynamics and communication

[00:11:55] - Analysis of the most challenging current team dynamic: managing multiple generational, cultural, and time zone differences simultaneously

[00:15:17] - How AI is already improving team communication by helping interpret tone and intent in written messages

[00:17:38] - Ilya's leadership philosophy: people-first approach, giving credit, encouraging autonomy and idea expression

[00:20:19] - Final LEGO build: Ilya's advice for new leaders featuring diverse colored elements surrounding a central figure

[00:22:14] - Ilya's reflection on the mental gymnastics of building thoughts with LEGO bricks

Key Themes Explored

Creative Freedom with Boundaries: The critical balance between giving teams autonomy to innovate while providing necessary structure and guardrails

Multi-Dimensional Team Challenges: Managing the complexity of generational gaps, cultural differences, and time zone variations in modern distributed teams

Communication Evolution: How AI tools are beginning to help teams navigate tone, intent, and asynchronous communication challenges

Show Don't Tell Leadership: Moving beyond verbal communication to demonstrate and visualize ideas for better team alignment

Diverse Perspectives: The importance of surrounding yourself with different viewpoints and avoiding echo chambers

Global Team Dynamics: Adapting leadership approaches for teams spread across continents with different working styles and cultural contexts

Notable Quotes

"You should give people the freedom to be able to experiment and do creative things... But it should give you the guardrails so you don't fall off the edge."

"I felt that every wrong move I could do... I could disappoint someone... and everyone's watching me. But I feel it's something a lot of people in their junior years feel similarly about."

"Sometimes just talking isn't necessarily good enough to convey. Not everyone can articulate how they feel. Like, show me whether it's your work or write it or something like that."

"I want my people to be the very best they can. One, they make me look good. They'll help me progress my career. So I have no reason to block people from taking all the credit doing cool projects."

"Be surrounded by people with diverse ideas. Don't be in an echo chamber... Try to be in the center of it, hear people out, different voices, different opinions."

About the Guest

Ilya Lazebnik is the Director of Infrastructure at Placer.ai, where he leads engineering teams behind large-scale cloud systems. With over a decade of experience in DevOps, cloud architecture, and automation, Ilya is known for driving innovation, building robust infrastructure, and championing modern engineering practices. He's a HashiCorp contributor and passionate advocate for open source and tech community knowledge sharing.

Find Ilya on LinkedIn and GitHub for his infrastructure and open source work.

About Herding Squirrels

Herding Squirrels is a podcast about modern teams, hosted by Brandon Wetzstein. Through LEGO® Serious Play® methodology and engaging conversations, the podcast explores the nuances of effective teamwork, leadership, and collaboration in today's evolving workplace.

Allison McHenry is currently serving as the CTO of Daily Kos, a progressive political blog. Previously, she was CTO at The Daily Beast, and has also held leadership roles at Meta and The New York Times. She most loves thinking about ways to enable teams to use technology to move socially conscious businesses forward.

Key Moments & Timestamps

00:00 - 01:11 - Personal Introduction Build

Allison builds a rotating model representing herself in the center trying to connect with her four daughters - two older ones in London and San Diego, and five-year-old twins at home.

01:26 - 03:11 - Best Team Experience: The New York Times

Discussion of leading the standalone product group at NYT, introduction to Paloma Medida's BICEPS model (Belonging, Improvement, Choice, Equality, Predictability, Status), and creating zero-to-one subscription businesses during a challenging time in media.

05:13 - 09:17 - Worst Team Experience: Leadership Under Pressure

Allison's powerful model of anxiety cascading down through organizational layers during uncertain economic times, exploring how external pressures create internal dysfunction and the challenge of maintaining team cohesion when basic security needs aren't met.

09:30 - 10:56 - The Evolution of Leadership

How remote work has required more intentional communication, cultural sensitivity, and leader availability, while also building trust through flexibility.

10:56 - 13:35 - AI's Impact on Media and Teams

Deep dive into how AI is transforming the media landscape, from Google's AI summaries affecting search traffic to the existential question of whether AI can replace entry-level positions, and the industry's struggle with data usage and monetization.

13:38 - 14:41 - Staying Grounded as a Leader

Allison's approach to managing information overload and maintaining strategic perspective while still being able to "turn it off and watch a movie, hang out with the cat."

15:05 - 17:02 - Advice for New Leaders

A powerful model showing two viable leadership paths (management vs. technical leadership), emphasizing self-awareness from the Master Trust equation, and the fundamental principle that leadership is ultimately about caring personally for people.

Key Topics Discussed

* BICEPS Model: Belonging, Improvement, Choice, Equality, Predictability, Status as team motivators

* Leading Through Crisis: Managing teams during economic uncertainty and external pressures

* Remote Leadership Evolution: Increased intentionality required for distributed team management

* AI's Disruption of Media: Search traffic impacts, data monetization challenges, and job displacement concerns

* Leadership Self-Care: Balancing information consumption with mental health

* Career Path Flexibility: Supporting team members in finding their authentic leadership style

Notable Quotes

On team motivation during crisis: "That externality of uncertainty makes everyone from leadership straight on down feel afraid, insecure, concerned about, am I going to lose my job? How am I being evaluated? Is this business even going to be around? There's a lot of anxiety."

On cascading pressure: "When that happens, what I've observed is people tend to push their anxiety down the leadership team. So they want to get more micromanaging, they want to get more in the weeds with what people under them are doing."

On remote leadership: "You have to be a lot more intentional about communication. If you're working with people in multiple time zones and multiple localities, you have to be much more culturally sensitive."

On AI's unprecedented impact: "The change with AI has been the single biggest shift I've seen in my career. I mean, I've never seen anything change so much in the past."

On leadership fundamentals: "No matter what you're doing, this is a people business and you have to care personally about your people. And that's like the thing that everything else comes from is, you know, that empathy and that desire to support people."

On self-awareness in leadership: "Knowing yourself and having that self-awareness is so critical to whether this is even what you want to do."

Where to find more Allison

* LinkedIn: Alison McHenry

Herding Squirrels is a podcast about modern teams, exploring how leaders navigate the complexities of today's workplace through hands-on LEGO® Serious Play® conversations.

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.

About Dave Walters

Dave Walters is the former CTO of Hired, Lacalle Group, and Spafinder Wellness, after spending 13 years at The Knot Worldwide (XO Group). He brings a strong track record in scaling platforms responsibly, operational rigor that supports both growth and margin, and de-risking complex technical initiatives. Beyond the boardroom, he's been a volunteer firefighter for over 20 years and thrives in high-stakes environments - whether it’s coordinating rope rescue teams, heading into burning structures, or setting the technical strategy to bring the business vision to life, he brings calm leadership where it counts most.

Find More Dave on LinkedIN

Episode Timeline

[00:00:00] - Introduction to Herding Squirrels podcast and guest Dave Walters[00:00:55] - First LEGO build: Dave creates a baseball diamond model representing his life outside work[00:03:02] - Discussion of Dave's baseball background as a catcher and how it shaped his leadership approach[00:04:01] - Second LEGO build: Dave's best team experience, featuring color-coded pathways converging on a common goal[00:06:56] - Exploration of team timing challenges and managing "FOMO" when teams join projects at different stages[00:07:30] - Third LEGO build: Dave's worst team experience model showing misaligned paths and disconnected effort[00:08:43] - Discussion of course correction and communication strategies when teams go off track[00:10:01] - Analysis of why teams fail to align (lack of context, missing the "why," team dynamics)[00:12:22] - Comparison of technical team leadership with other leadership contexts[00:14:15] - How baseball and firefighting experiences influenced Dave's leadership philosophy[00:17:16] - The importance of staying calm under pressure and maintaining perspective[00:19:26] - Discussion of how remote work and technology shifts have impacted technical teams[00:20:46] - Dave's thoughts on AI as a transformative force for engineering roles[00:21:42] - Final LEGO build: Dave's advice for new technical leaders featuring a growth staircase with support structures[00:24:32] - Dave's reflection on the LEGO building process and wrap-up

Key Themes Explored

Team Alignment: Creating clear pathways toward common goals despite different starting pointsCalm Leadership: Bringing perspective from firefighting experience to business challengesContinuous Growth: The importance of mentorship and evolution throughout leadership journeysCourse Correction: How to identify and address teams moving in the wrong directionTechnical Context: Bridging the gap between technical teams and business leadershipAdaptability: Embracing technological change and continuous evolution

Notable Quotes

"I think in the business world, all too often, we operate like a set of individuals... High-performing teams know when to stay in their lane, but also when to pick things up that are outside their lane because it's necessary for success."

"An individual success is meaningless if the company as a whole is failing."

"When you're having a rough day or facing a tough scenario in the business world... This is not life and death. It's important, but it's not life and death."

"If you dig in your heels and refuse to change, you're going to get left behind... You have to embrace that change."

"That mentor that maybe got you from a senior engineer to an engineering lead may not be the same mentor you're going to need when you're going from a VP of engineering to a CTO."

About Herding Squirrels

Herding Squirrels is a podcast about modern teams, hosted by Brandon Wetzstein. Through LEGO® Serious Play® methodology and engaging conversations, the podcast explores the nuances of effective teamwork, leadership, and collaboration in today's evolving workplace.

Episode Overview

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.

Through hands-on building exercises, John demonstrates key leadership principles including taking responsibility for failures while sharing credit for success, the importance of direct communication about trust, and why understanding your team members as individuals is crucial for effective collaboration. The conversation touches on everything from DIY projects and parenting moments to AI's impact on hiring, all while building physical models that bring abstract leadership concepts to life.

This episode is perfect for technical leaders, engineering managers, and anyone interested in building stronger, more trusting teams through authentic leadership practices.

Episode Timeline

[00:00:01] - Introduction to Herding Squirrels podcast and guest John Fly, CTO of FirmPilot[00:00:26] - Discussion of John's favorite LEGO builds, including Star Wars AT-AT walkers built with his son[00:01:00] - First LEGO build: John creates a model representing his life journey outside of work, focusing on continuous growth and DIY passion[00:02:12] - Deep dive into John's DIY projects, from irrigation systems to car restoration, influenced by his father's encouragement to fix things[00:03:23] - Second LEGO build: John's best team experience, building a bridge model representing leadership vulnerability and team support[00:05:04] - John shares the origins of his leadership philosophy, stemming from negative experiences with unsupportive managers, including a supervisor who called him at the hospital[00:08:49] - Transition to exploring barriers to teamwork rather than worst team scenarios[00:09:22] - Third LEGO build: John creates a "ruler/king" model showing how individual kingdom-building undermines teamwork[00:11:07] - Discussion of partnership vs. zero-sum thinking, using technology/sales collaboration as an example[00:13:33] - Sports team analogy extension about individual excellence within team success[00:14:20] - John's evolution from "tech purity" mindset to "how do we win together" approach over 20+ years[00:16:39] - Impact of AI on hiring practices, with developers using AI during interviews[00:17:03] - John's direct approach to building trust in leadership, including examples from joining FirmPilot[00:19:01] - Discussion of trust maintenance and vulnerability in leadership relationships[00:20:13] - Current use of AI in leadership for adapting communication styles to different team members[00:22:41] - Fourth LEGO build: John's advice for new technical leaders, featuring a flag, resources, and multiple paths model[00:24:02] - John's reflection on the LEGO building process being more challenging than expected due to constraints[00:24:27] - Wrap-up and contact information for John Fly

Key Themes Explored

* Trust-Based Leadership: Direct communication about trust needs

* Servant Leadership: Taking responsibility for failures, sharing credit for success

* Partnership Mindset: Moving beyond zero-sum thinking

* Adaptive Leadership: Continuous learning and flexibility

* Communication Adaptation: Tailoring style to individual team member needs

Notable Quotes

* "If we fail, it's on me... if we win, it's the team that did it"

* "I wanted to be the manager I wished I had"

* "Don't pick a solution before you really understand the problem"

* "We're going to win this game together or lose this game together"

Where to Find John Fly

Website: JohnFly.comLinkedIn: linkedin.com/in/johnfly

Meet Jessica Mosley, a quality engineering virtuoso who’s been wrangling tech teams, dodging bureaucracy, and making waves in the software world for over 20 years. She’s got the kind of experience you just can’t fake, having tackled everything from software development to DevOps, IT, and Customer Experience. If there’s an inefficiency lurking in a process, Jessica’s the one to spot it, and she’ll do it with a grin and maybe just a touch of sarcasm.

But don’t let her laid-back style fool you. Jessica’s fierce about quality. For her, it’s not just a metric, it’s a way of life. She’s on a mission to show that a quality mindset can turn a good company into a great one and that the real secret to success is found in building stronger connections between people, not just polishing the code. As a keynote speaker, Jessica’s known for blending real talk with charm, captivating audiences as she shares how prioritizing quality can elevate a workplace, boost morale, and yes, maybe even make work enjoyable.

Jessica’s talks are a mix of humor, hard-earned wisdom, and a nudge to look at quality in a whole new way. Get ready for a fresh perspective that’ll make you rethink what it really means to succeed.

Episode Description: 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.

Time Stamps:

[00:00:01] - Introduction to Herding Squirrels podcast and guest Jessica Mosley

[00:01:02] - First LEGO build: Jessica shares her life outside of work, including gaming, plants, and family connections

[00:02:37] - Jessica discusses her current gaming interests, including Destiny and Doom Legends

[00:03:22] - Second build: Jessica describes her best team experience at a Taiwanese company

[00:05:25] - Discussion about facing barriers in new jobs and how they can become bridges for growth

[00:06:46] - The importance of a supportive team that "looks out for" members versus monitoring them

[00:07:54] - Jessica shares a powerful first-day story about handling a "catastrophic failure" with team support

[00:09:17] - Third build: Exploring Jessica's worst team experience

[00:11:30] - Breakdown of team dysfunction: spread thin resources, silos, and leadership that "sets things ablaze"

[00:12:00] - Discussion on the foundational reasons for poor team dynamics, including fear and vulnerability

[00:13:15] - How the pandemic changed workplace dynamics and created new power currencies in distributed teams

[00:13:50] - Jessica's leadership journey and how she initially never planned to become a leader

[00:15:38] - Surprising leadership insight: "It's more like relationships than people think"

[00:16:56] - The biggest change in leadership post-pandemic: the increasing need for empathy and people leadership

[00:18:17] - Final build: Jessica's advice for new leaders - "Come in as your authentic self"

[00:19:18] - Jessica's reflection on the LEGO Serious Play experience

[00:19:54] - Where to find Jessica online (LinkedIn, Blue Sky, and Instagram)

Featured Quotes:

"How can we help you in going forward in this?" - Jessica sharing the supportive approach of her best team experience [00:08:05]

"Your team isn't expecting Tony Robbins or Lee Iacocca or something like that. They're expecting you." - Jessica's advice for new leaders [00:19:06]

Connect with Jessica Mosley:

* LinkedIn: https://www.linkedin.com/in/jessmosley/

* Insta: https://www.instagram.com/guruofqualitea/

* BlueSky: ‪@guruofqualitea.bsky.social‬

About Herding Squirrels: Herding Squirrels is a podcast about modern teams, hosted by Brandon Wetzstein of IN8 Create. Through LEGO® Serious Play® methodology and engaging conversations, the podcast explores the nuances of effective teamwork, leadership, and collaboration in today's evolving workplace.

Frédéric is the Chief Technology Officer at Dashlane, a leading cybersecurity company specializing in credential management and digital identity solutions. With over two decades of experience in tech leadership, Frédéric drives innovation in security and privacy. A passionate advocate for user-centric security, he brings a unique perspective on blending convenience and robust protection for both individuals and businesses.

Find Frédéric online and at the Dashlane Blog: https://www.dashlane.com/blog

Episode Highlights

[00:03:52] The foundations of great teams: shared mission and unity[00:06:29] Building consistency and unity in teams intentionally[00:07:33] The importance of intimacy and vulnerability in team relationships[00:08:18] The trust equation: credibility, intimacy, and self-awareness[00:09:14] Dysfunctional teams: the illusion of alignment[00:11:39] Recognizing when teams are not truly aligned[00:14:54] Balancing business demands with team development[00:16:55] Remote work: advantages and challenges for teams[00:19:28] Finding balance in return-to-office policies[00:21:36] The evolving role of a CTO through different company stages[00:23:13] Leadership advice: taking one step at a time on your journey[00:24:47] The importance of extending your network as you grow in leadership[00:25:50] Using games and play to foster team learning and connection

Key Insights

* Unity and Consistency: Frédéric emphasizes that great teams have a shared mission and direction, along with a unity that doesn't mean everyone is the same, but rather a consistency in how people approach work together (00:03:52)

* Intentional Relationship Building: Being intentional about building team relationships is essential - it doesn't happen by magic. Teams need to spend time getting to know each other both professionally and personally (00:06:29)

* The Power of Intimacy: Frédéric believes in the importance of intimacy within teams, allowing vulnerability and authentic sharing that creates deeper connections (00:07:33)

* The Illusion of Alignment: One of the biggest challenges in dysfunctional teams is what Frédéric calls "the illusion of alignment" - where people say yes but don't actually support decisions in practice (00:09:14)

* Remote Work Balance: While remote work offers flexibility and individual productivity benefits, it creates challenges for building culture, innovation, and maintaining mental health (00:16:55)

* Leadership as a Journey: Frédéric uses the metaphor of a staircase to describe leadership development - it's a journey with different steps that shouldn't be rushed (00:23:13)

* Expanding Networks: As you grow in leadership, you need to extend your network further away from your immediate team to continue learning and developing (00:24:47)

Resources Mentioned

* The Manager's Path by Camille Fournier

* Dashlane Blog: https://www.dashlane.com/blog

* Trust Equation (framework mentioned that includes credibility, intimacy, and self-awareness)

Herding Squirrels is a podcast about modern teams, where we uncover the nuts and bolts of effective teamwork.

Herding Squirrels Episode 3: Building Bridges and Breaking Patterns with Cole Christie

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.

Episode Highlights

The Art of Team Communication

Cole emphasizes that communication breakdowns are universal challenges across all industries and experience levels. He memorably explains that "you don't bring facts to a feelings fight" – highlighting the importance of understanding emotional contexts before attempting to resolve technical disagreements. According to Cole, genuine curiosity and asking questions without assuming the answers are crucial to effective leadership.

From Individual to Team Perspective

Cole's journey from engineer to leader taught him an essential shift in thinking: moving from "I can do something" to "we can do something." This transition means focusing less on personal capabilities and more on enabling the entire team to succeed together. Cole explains how this requires understanding team members' perspectives, learning about their beliefs, and respecting their experiences.

Building Strong Teams Through Challenges

Using a powerful blacksmithing analogy, Cole describes how teams are forged through overcoming difficulties together. Like metal that's heated and hammered repeatedly to gain strength, teams develop cohesion by facing and conquering challenges as a unit. This process helps transform a collection of individuals into a truly unified team.

Remote Work and Team Building

Cole discusses how the pandemic fundamentally changed team dynamics, creating new challenges for building connection in distributed workforces. While technological tools have improved our ability to collaborate remotely, he emphasizes focusing on smaller, daily interactions to build team cohesion when large in-person events aren't possible.

The Cup of Learning

In his final LEGO® model, Cole presents a simple yet profound piece of advice for new leaders: maintain an open mind and never stop learning. What appears as a solid block from the outside is actually a cup – representing how leaders should remain receptive to new ideas and knowledge every day.

Key Takeaways

* Effective team leadership requires empathy and understanding different perspectives

* Communication failures often stem from focusing on facts when emotions are involved

* Strong teams develop through shared challenges and experiences

* Remote work demands creative approaches to building team connections

* Continuous learning and openness are essential for leadership growth

Don't miss this insightful conversation about modern team dynamics, leadership evolution, and how to build bridges across different perspectives through effective communication and shared purpose.

Herding Squirrels uncovers the nuts and bolts of teams with host Brandon Wetzstein. Follow us for more insights on team leadership, collaboration, and modern workplace dynamics.

Cole Christie is an experienced Engineering Leader with 18 years in the field, including 10 years in management roles. Starting his career in System Administration, his technical expertise spans various domains, including software development, architecture, distributed systems, and automation. Cole is proficient in multiple programming languages and has extensive experience with cloud technologies like AWS, Kubernetes, and observability tools.At GAP Inc., Cole leads the Site Reliability Engineering (SRE) team, implementing automation and driving reliability improvements across the organization. His efforts have streamlined processes and reduced false alarms, significantly enhancing team performance. Prior to GAP, Cole worked across diverse industries including SMS advertising, healthcare, academia, and defense subcontracting. Despite the varied industries, his focus remains consistent: helping people bring their best selves to work to achieve collective success.Cole holds a Master's degree in Information Security from Georgia Tech and a Bachelor's degree in Information Systems from UCR. His leadership style is influenced by principles from "Extreme Ownership," "Growth Mindset," and "Start with Why."

Find Cole on LinkedIn: https://www.linkedin.com/in/mrcolechristie/

Episode Overview

In this episode, host Brandon welcomes Jiovanni Rosario, Controls Engineering Manager at Amazon. Using LEGO Serious Play methodology, they explore Jiovanni's journey from individual contributor to leader, discussing team dynamics, leadership challenges, and strategies for effective management.

Guest Bio

Jiovanni Rosario has worn many hats in the tech industry—controls engineer, sales engineer, and software developer. These days, he manages a team of controls engineers keeping data center servers cool and powered. He shares leadership stories on Substack, mentors aspiring managers, and recently became a dad.

Key Moments & Topics

The Best Team Experience (08:52-11:12)

* Jiovanni’s "A-team" story about his formative years in the data center industry

* Three colleagues who clicked, challenged each other, and maintained friendship for a decade

* The power of camaraderie in professional settings

The Worst Team Experience (11:12-14:18)

* Jiovanni's challenging experience in a sales engineering role

* Poor leadership characterized by isolation and lack of support

* The importance of connection versus silos in team environments

The Journey to Leadership (14:18-18:08)

* Motivation to not repeat negative management experiences

* Learning to tailor communication approaches to different team members

* Focusing on trust and curiosity rather than instant advice-giving

Managing Cross-Functional Demands (18:08-23:57)

* The challenge of balancing organizational goals with team capacity

* Using prioritization frameworks to focus team efforts

* Strategies for evaluating and sometimes redirecting partner requests

Advice for New Leaders (25:36-28:57)

* "Life exists outside the spreadsheet" - balancing metrics with human connection

* The importance of face-to-face interaction with team members

* Avoiding getting lost in data at the expense of understanding real pain points

Growth Mindset for ICs (23:57-25:36)

* "Think big" as a critical leadership principle

* Moving beyond solving individual problems to identifying patterns

* Looking for opportunities to improve processes for everyone

Quotes

"When I first got the opportunity to become a manager... I didn't want to be a bad manager. I wanted to be someone who cared, someone who supported their team and someone who made their team feel like they could trust them."

"Life exists outside the spreadsheet. It's really easy to get lost... looking at charts and different data analytic tools, that you lose sight of really interacting with your team and potentially even your customers."

Resources Mentioned

* Bob Iger's Masterclass on team focus

* "Build" by Swarmia - featuring the Eisenhower Matrix for prioritization

* Ramit Sethi's book "I Will Teach You to Be Rich" (for the quote about life existing outside spreadsheets)

Where to Find Giovanni

* LinkedIn https://www.linkedin.com/in/jiovannirosario/

* Substack

* Medium https://jiovannirosario.medium.com/

About the Show

Herding Squirrels explores team dynamics through LEGO Serious Play methodology, uncovering insights about leadership, collaboration, and effective teamwork.