Herding Squirrels

Created and Hosted by Brandon Wetzstein
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Ever tried to get a group of squirrels to move in the same direction? Welcome to modern teamwork! Herding Squirrels is a podcast that explores the chaotic, wonderful, and sometimes maddening world of teams in our hyperconnected age. From Slack notifications pinging like acorns falling from a tree to the constant scatter of competing priorities, we dive into what makes teams tick. herdingsquirrels.substack.com

  1. Herding Squirrels Ep 20 w Gowri Sivaraman

    11/20/2025

    Herding Squirrels Ep 20 w Gowri Sivaraman

    Episode Overview 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. About Gowri Gowri Sivaraman] is a visionary technology leader with over 25 years of experience shaping multi-million-dollar products across the globe. She’s built and scaled digital consumer, small business, and fintech solutions that millions rely on every day — from AI-driven platforms to the devices we use in our pockets. Known for blending big-picture vision with hands-on execution, Gowri has a track record of turning ideas into innovations that not only engage users but also fuel significant business growth. Timestamps [00:00] Introduction and welcome[00:40] Build #1: Who Gowri is outside of work—gardening, automation, and building things that grow[02:10] Build #2: Best team experience—QuickBooks Capital’s journey from COVID startup to flagship product[04:45] Keeping your eye on metrics and KPIs as you scale[05:03] Build #3: Nightmare team scenario—when everyone runs in different directions without a shared vision[06:52] Build #4: Leading through uncertainty—adaptability, role modeling, and painting vision for the team[09:39] Staying on top of market changes: TLDR AI, conferences, and dedicating 10% of time to industry learning[12:41] Global Engineering Days at Intuit—a full week for experimentation[13:07] Building cross-functional accountability without being abrasive—using data to separate person from problem[16:09] Building fun and camaraderie: Top Gun, Top Golf, and the power of team activities[17:36] The basketball moment—how showing vulnerability inspired a team member[19:05] Build #5: Leadership advice—stay true to your north star and build a community you can lean on[20:49] Gowri’s reflection on building with LEGO bricks Notable Moments “The constant is change.” Gowri’s framework for leading through uncertainty starts with accepting that flux is the norm—and then equipping yourself and your team with the right tools and learning mindset to adapt. Separate the person from the problem. When holding cross-functional teams accountable, Gowri emphasizes using data and facts rather than finger-pointing. Lay out the evidence of what happened, and the actual person becomes secondary to solving the problem. Vulnerability builds trust. Gowri shared a story about playing basketball at a team event despite having no skills—and kept trying anyway. A team member later told her how inspiring it was to see a leader be okay with failing publicly. Sometimes the low-stakes moments create the biggest lessons. “Never take your eye out of sight.” Her best team build featured an eyeball at the top—a reminder that as teams and technology grow, you must maintain clear focus on what matters: customer outcomes and system stability. Where to Find Gowri LinkedIn: Gowri Sivaraman This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com

    22 min
  2. Herding Squirrels Ep 19 w Barninder Khurana

    11/13/2025

    Herding Squirrels Ep 19 w Barninder Khurana

    Episode Overview Your latest team probably isn’t broken—it’s just been handed impossible expectations. Barninder Khurana, CTO of CoverWhale, knows this intimately. After a decade-plus navigating the insurance tech space as CIO of GeoVera and leading digital transformation at ProSight, he’s discovered that most organizational change initiatives fail not because teams lack skill, but because leaders treat transformation like a separate function instead of building it into the team’s DNA. 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. You’ll hear why Barninder writes lists of life goals (and actually follows them), how he approaches parenting with ADHD as a research project, and why his dog sits next to his wife in LEGO form but probably nowhere else. Most importantly, you’ll understand why the future of AI adoption isn’t about building something revolutionary—it’s about composing specific solutions for specific problems, and why your existing team is better positioned to do that than any outside hire. Guest Bio Barninder Khurana is CTO of CoverWhale, where he helps insurance organizations move faster, work smarter, and grow profitably. With over a decade of leadership across the MGA and carrier space—including roles as CIO of GeoVera and leading digital transformation at ProSight—Barninder brings a pragmatic perspective on building high-performing teams through rapid change. When he’s not leading technology transformation, you’ll find him on his motorcycle (unless there’s ice on the ground), reading voraciously, or researching everything from ADHD parenting strategies to the next item on the life goals list he wrote at 21. Connect with him on LinkedIn. Timestamps & Key Moments 00:00 - 04:14 | Who Barninder Is Beyond Work Father of three boys, motorcycle rider, perpetual learner. His growth mindset extends beyond work—when his youngest was diagnosed with ADHD, he and his wife researched extensively, consulted doctors, and interviewed other parents. Before having kids, they interviewed couples whose children they admired to build mental models for parenting. 04:15 - 07:20 | Building High-Efficiency Teams The best teams have unity of thought before execution alignment. Leaders must know when to lead from the front, from behind, or get out of the way entirely. Empowerment means understanding what motivates each team member rather than defaulting to “just replace people.” 07:21 - 10:45 | The Ladder as Escape Route Not everyone will fit your approach, even with effort. The ladder represents recognizing when someone’s emotional baggage or resistance prevents progress—and knowing when to create an exit path rather than forcing alignment. 10:46 - 14:30 | Navigating Restructures and Mergers Barninder’s real-world experience: acquisition eliminated his entire team, he retained one person while rebuilding from scratch. The key to leading through restructures is building trust early, understanding your new peers, and knowing when to make difficult decisions about fit. 14:31 - 18:05 | Worst Team Experiences Toxic environments where people won’t help each other because “that’s not my job.” Barninder learned the hard way: no amount of process can fix fundamental trust issues. You either fix the culture or accept you’re managing dysfunction, not building a team. 18:06 - 21:04 | AI as Composition, Not Revolution The future isn’t one AI solving everything—it’s composing specialized solutions for specific problems. Generic models lack the precision needed for trust. The next wave: specialized AI for legal teams, medical diagnosis, contract analysis. Then comes composition: combining solutions to solve your unique operational challenges. 21:05 - 24:24 | Why Upskilling Beats Hiring Specialists Controversial take: Creating separate “AI teams” or “digital transformation officers” fails because they operate outside organizational DNA. Your existing team already knows your company, culture, and technology—upskill them rather than hiring specialists who’ll need months to understand context. This approach is more cost-efficient and builds lasting capability. 24:25 - 25:37 | Reflection on LEGO Serious Play First-time experience with LSP. Barninder found translating thoughts into visual brick representation harder than expected—but valuable for expressing complex ideas differently than verbal communication allows. Notable Notes “Unity of thought comes before execution alignment.” Most leaders jump straight to “how” before ensuring everyone agrees on “why” and “where.” Get alignment on the goal first—then diverse approaches to execution become strengths rather than sources of conflict. The innovation culture paradox: You can’t bolt innovation onto an organization through specialist hires. Building innovation into your team’s DNA means empowering people who already understand your business to solve problems with new tools, rather than hiring external experts who’ll battle existing culture. The digital transformation lesson: Remember when companies hired Chief Digital Officers and dedicated transformation teams? They failed because existing teams said “that’s your job, not mine.” AI adoption is following the same pattern—separate AI teams building parallel data stores that won’t sync with core systems. Learn from history: integrate new capabilities into existing teams rather than creating organizational silos. Growth as identity: Barninder’s approach to growth—reading, learning, evolving as parent/professional/person—extends beyond self-improvement platitudes. He researches parenting strategies like a technical problem, interviews role models before major life decisions, and maintains a life goals list from age 21 that he’s still actively working through. The emotional baggage reality: Even with excellent leadership and clear vision, some people carry baggage that prevents them from moving forward. The ladder in Barninder’s model represents recognizing this reality—sometimes the most compassionate leadership decision is creating an exit path rather than forcing someone to stay in a role that isn’t working. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com

    26 min
  3. Herding Squirrels Ep 18 w Boomie Odumade

    11/10/2025

    Herding Squirrels Ep 18 w Boomie Odumade

    Guest Bio Boomie Odumade is a senior engineering leader and fractional leader of Engineering who builds high-performing, secure, and resilient engineering organizations. She coaches engineers and engineering leaders, partnering with them to grow their capabilities and reach their goals. Outside of work, she’s active in the tech community, mentors youth, and enjoys salsa dancing, exploring creative adventures with her kid, and building LEGO botanical sets. Episode Summary 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. Episode Overview In this conversation, Boomie builds four LEGO models that reveal her philosophy on engineering leadership: Personal Introduction Boomie shares her life outside work through physical activity (salsa dancing, half marathons), quality time with her kid, building LEGO botanical sets, and self-care through hiking and theater. Best Team Experience: The Power of Direction Using a boat model, Boomie illustrates what makes great teams work: clarity and direction, leaders who guide without micromanaging, teams aligned and moving together, and celebration of wins that prepare for the next challenge. Worst Team Experience: Misalignment and Roadblocks Her model captures the dysfunction patterns: being pulled in multiple directions with inconsistent information, disempowering micromanagement, “us vs. them” mentality, and the resulting roadblocks and demotivation. The root cause? Lack of shared context, goals, and understanding of how different teams contribute to success. The Silent Objection Problem Boomie reveals a powerful observation: people nod in agreement during meetings, then express their real concerns in smaller groups afterward. Why? Fear of looking less knowledgeable, challenging leadership, or being “that person” who always questions things. The solution is creating explicit safety for questions and concerns. Meeting Structures That Work Two types transform teams when done authentically: retrospectives that create safe spaces for real feelings and accountability for change, and monthly all-hands that reinforce shared goals and create leadership touchpoints. The warning: fake retrospectives that don’t lead to change erode trust. The AI Leadership Challenge Boomie addresses the dual fear problem: executives afraid of falling behind, engineers afraid of losing jobs. Her approach balances showing both capabilities and limitations, presents the full context (including “AI deleted the database” stories), and focuses on business case specific to the team’s actual needs and structure. Addressing Fear at All Levels With engineers, she builds relationship and trust to surface concerns. With leadership, she finds words that show understanding while positioning as a partner focused on shared goals—whether those goals are fear-based or not. The CTO Balancing Act Boomie’s final model captures leadership as four simultaneous balances: business goals vs. people needs (these don’t compete), transparency vs. information control (people imagine the worst without enough info), hands-on involvement vs. delegation (don’t stunt growth), and burnout prevention (taking care of yourself, your people, and the business together). Connect with Boomie * LinkedIn: linkedin.com/in/odumade * Fractional Leadership Services: techbees.me * Slack Communities: Active in SheTO, Rands Leadership Slack, and other tech communities Key Takeaways * Great teams share three essentials: clarity, direction, and alignment * The “us vs. them” dynamic stems from lack of shared context and goals * Silent objections in meetings are more dangerous than voiced concerns * AI adoption requires acknowledging fears at all organizational levels * CTO leadership is fundamentally a balancing act between business, people, and sustainability * Transparency reduces anxiety—when people don’t have information, they imagine the worst * Creating psychological safety for questions prevents surface-level agreement that masks resistance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com

    23 min
  4. Herding Squirrels Ep 17 w Rosemary Sanchez

    11/06/2025

    Herding Squirrels Ep 17 w Rosemary Sanchez

    Herding Squirrels Episode 17: Rosemary Sanchez on Leadership, Team Mergers, and Thriving Through Chaos Rosemary Sanchez brings over seven years of leadership experience from a strong technical background, managing both remote and co-located teams through various stages of growth. In this conversation, she 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. Timestamps 00:00 - 02:26 Introduction and personal foundation Rosemary builds her story of growing up with immigrant parents from the Philippines, how her family’s foundation of education and kindness shaped her values, and the symbols she uses to represent love, accomplishment, adversity, and wonder. 02:27 - 06:46 Best team experience: Merging two teams The story of merging two engineering teams with different cultures and ceremonies into one cohesive unit, culminating in a risky visual design system overhaul that touched every UI element in a live product with thousands of users. 06:47 - 09:22 The anatomy of team success How intentional social activities, celebrating small wins, and building comfort with uncertainty created the foundation for the team to handle high-pressure moments without needing orchestration from leadership. 09:23 - 13:17 Worst team experience: Silos and micromanagement The challenges of joining a team with siloed departments, lack of psychological safety, and a culture where information was hoarded rather than shared, leading to distrust and defensive behavior. 13:18 - 16:59 Navigating organizational change and uncertainty Practical strategies for managing through reorgs, restructures, and uncertainty - including knowing when to have conversations, protecting team focus, and avoiding “thrashing.” 17:00 - 20:28 State of thrash and using AI as a leadership tool Defining the concept of “thrashing” - expending energy without direction - and how AI can help leaders tap into anonymous wisdom, challenge biases, and find blind spots when working with confidential information. 20:29 - 23:46 Leadership advice and closing thoughts Rosemary’s model of leadership for new ICs: embrace the wobbly feeling, lean on diverse perspectives, practice transparency, share both successes and struggles, and recognize that adversity might be a friend in disguise. Key Quotes On team success: “I didn’t need to orchestrate anything. The team knew who could handle what. People were quick and efficient, and they just cared about each other in that moment. We didn’t want to let each other down.” On the danger of silos: “When you silo teams and they don’t have information, it creates this mistrust where they think, ‘well, I don’t really want to help this other team because I don’t trust them or I don’t really know what they’re working on.’” On leadership during uncertainty: “You leaning in and just being a shoulder to help with those emotions and understand like, hey, this is one data point, we don’t know what’s going to happen, but I will be here for you, I think is very important.” On thrashing: “It’s like when you’re just trying to tread water and you’re thrashing water around. You’re not using that same energy to like, I’m going to swim in that direction. You’re just expending energy, getting nowhere and just patting yourself on the back for staying afloat.” On leadership for new leaders: “Leadership is going to feel wobbly at first. Lean on diversity and other people’s perspectives to help you along the way. No matter where you go, keep climbing, letting people in to your successes and your sad moments will feel uncomfortable, but it will tap in a level of empathy and more understanding.” Connect with Rosemary Find Rosemary on LinkedIn - she’s an introvert who keeps a low social media profile but will probably reply to your message. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com

    24 min
  5. Herding Squirrels Ep 16 w Jossie Haines

    10/29/2025

    Herding Squirrels Ep 16 w Jossie Haines

    Herding Squirrels Podcast: Jossie Haines on Leadership Transitions and Leading Through Change Episode Overview 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. Episode Timestamps 00:00 - Introduction: Who is Jossie Haines and why tech leaders seek her coaching00:48 - First Build: Life outside of work—palm trees, hammocks, and choosing a different path02:52 - Best Team Experience: The Zynga story—when 1,000 people built a social network in two weeks06:39 - Worst Team Experience: What happens when your team falls apart (and what to learn from it)10:15 - Managing Change: Why engineers need to grieve before they can move forward23:21 - Leadership Advice Build: The three-pillar framework for new leaders28:06 - Reflection: What it’s like building thoughts with LEGO bricks29:02 - Where to find Jossie and access her AI workflows guide Notable Quotes On the power of mission alignment:“I’ve never seen the entire rest of the time in my career, watching so many people just get aligned on a mission. We worked crazy hours... and really thrived and created something by the end of the two weeks.” On helping engineers through change:“The more we help people actually process the human emotions, the better it would be to actually then be able to go and get the change navigated sooner and more effectively, instead of having people feel like, oh my gosh, I have to just pretend I’m totally happy with all these changes.” On the reality of leadership:“The biggest leaders are not the ones—they’re enabling their teams to make the huge impacts. And that is how they are doing the impact. But you might stop getting as much recognition as you were as an IC.” On the three pillars of leadership:“You’re managing yourself. You’re managing your team. And you’re also managing up to your leadership level... And this is really your job.” On why people become leaders:“When people go to become leaders, I really focus on why. And part of it needs to be, I really care about growing and developing individuals, because that is what the huge part of leadership is all about.” Where to Find Jossie You can connect with Jossie Haines and access her resources: LinkedIn: Connect with JossieWebsite: jossiehaines.comYouTube: @jossiehainesFree Guide: 4 AI Workflows Every Engineering Leader Should Automate Herding Squirrels is a podcast about modern teams, hosted by Brandon Wetzstein. Each episode uses LEGO® Serious Play® methodology to help leaders uncover insights about team dynamics, leadership, and what makes teams actually work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com

    30 min
  6. Herding Squirrels Ep 15 w Harini Rajagopal

    10/23/2025

    Herding Squirrels Ep 15 w Harini Rajagopal

    Herding Squirrels Podcast: Harini Rajagopal - Building Resilient Teams Without Burning Out Guest Bio Harini Rajagopal is a data engineering leader who specializes in building scalable, robust data pipelines that manage terabytes of information. She expertly combines software development rigor with strategic execution to drive business value. A recognized thought leader and AWS Game Day champion, Harini is a frequent speaker sharing expertise on building resilient data teams and preventing burnout. Beyond her technical leadership, Harini pursues a new hobby every year—from learning to swim as an adult to studying classical dance from South India. She’s an active member of SheTO, an organization supporting women in technical leadership. Episode Overview 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. Episode Timestamps [00:00:00] Introduction to Herding Squirrels and Harini Rajagopal[00:00:32] Building a model of herself—standing on uneven ground with support from family, skills, and learning[00:02:40] Harini’s yearly hobby tradition and this year’s pursuit: classical dance from South India[00:03:28] The best team experience: COVID, remote work, and why it was amazing[00:04:22] Core foundations: You as a person matter more than nine-to-five work[00:05:01] “Nobody’s making you sit at a job here”—the anti-micromanagement philosophy[00:05:25] Collaboration that climbs: morning Wordle, genuine care, and silent Slack co-working[00:06:46] Personal growth alongside team growth—being nerdy, fun, and vulnerable together[00:08:12] The nightmare team model: unclear expectations, abandonment, and drowning in work[00:11:08] What keeps leaders up at night: team burnout and the impossible balance[00:14:47] The reality of layoffs and supporting teams through organizational change[00:17:16] Balancing time pressure with team care—the honest answer[00:18:34] “When you have three options, work on making those options 30”[00:19:17] Leadership advice model: Consistent messaging, being a ladder for growth, and being a green flag[00:20:57] “You’re not there to parent them. You’re there to help them grow.”[00:21:24] Reflections on building with LEGO bricks—nervous but enlightening[00:22:12] Where to find Harini and learn about SheTO Notable Quotes On anti-micromanagement:“Nobody’s making you sit at a job here. So I am not going to micromanage you. You know how to do your job.” On being honest as a leader:“Can I be honest and say, I don’t know anything at all. And sometimes I don’t know how to do it either. I’m going to have to go find out the answer for you, but I will find an answer.” On expanding your options:“When you have three options, always work on making those options 30. There’s never just three options, there’s always 30.” On the role of a leader:“You’re not there to parent them. You’re there to help them grow. That’s it.” Where to Find Harini LinkedIn: Connect with Harini Rajagopal on LinkedInSheTO: Learn more about SheTO, an organization supporting women in technical leadership Herding Squirrels is a podcast where we uncover the nuts and bolts of teams, exploring what makes them work, what breaks them, and how to build something better. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com

    23 min
  7. Herding Squirrels Ep 14 w Adam Tal

    10/22/2025

    Herding Squirrels Ep 14 w Adam Tal

    Herding Squirrels Podcast: Adam Tal - Building Teams That Thrive in Complexity Guest Bio Adam Tal is the Director of Payments Engineering at Vimeo, where he’s spent the past five years leading the teams responsible for Vimeo’s global commerce systems—from billing and payments to fraud prevention and compliance. His career spans multiple industries including fintech, edtech, fashion, and consulting, giving him a unique cross-industry perspective on how technology and business intersect. Adam is passionate about building teams that thrive in complexity, where trust, autonomy, and growth fuel meaningful work. When he’s not leading engineering teams, you’ll find him in the suburbs with his wife Kim, son Daniel, and dogs Lady and Norma, or getting his workout in at Orange Theory. Episode Overview 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. Episode Timestamps [00:00:01] Introduction to Herding Squirrels podcast and Adam Tal[00:00:37] Adam builds a model about himself—family, nature, Orange Theory, and suburban life[00:01:36] The best team experience: Purpose, resources, transparency, and good vibes[00:03:32] The nightmare team model: Panic, misalignment, and fighting for relevance[00:06:11] Building a model of what keeps leaders up at night—strategic alignment, market uncertainty, and AI adoption[00:08:38] The challenge of balancing high performers with those falling behind[00:10:18] AI’s impact on teams: The full spectrum from moral opposition to enthusiastic prototyping[00:14:01] Why you can have both amazing and terrible experiences at the same organization[00:15:22] The value of staying long enough to see the outcomes of your decisions[00:16:24] Adam’s leadership advice model: Building a stable platform that protects the team[00:18:03] Final reflections on building with LEGO bricks Notable Quotes On great team experiences:“This is somebody with purpose. This is somebody happy and productive. And they are walking with purpose directionally... The base of it, the yellow, I would say, is sort of objective. This is a person who knows what is expected of them. And then this green piece is, I would say, the resources they need to get the job done, right? They know what is expected of them. They have what they need to get the job done. And then the top one is transparency and clarity and feedback.” On nightmare team dynamics:“I mean, this is the opposite. This is a complete mess. This is panic. This is misalignment... You have a lot of members like this, and there’s no comfort here. There’s no progress. You’re fighting for relevancy, and every day you sort of have to start from scratch and redefine your role and your position.” On leading through change:“Things happen. Leadership changes, product direction changes, market conditions change, and it’s very easy to disrupt the comfort zone of, you know, I have my purpose, I have my resources, I have my feedback, and, you know, I just want to do my job, and I want it to be sort of consistent, and sometimes you don’t get that, and so you have to... You have to maintain this balance of living in the present and doing your job, but also evaluating how is this going to change and is it changing? And if things are going bad, what is bad about it? Who can I talk to about this and what can we do about it and how quickly can we react to that?” On tenure and growth:“I encourage people to stay at an organization long enough to see some change. Hopefully, you stayed in the organization long enough that you can make some decisions and then see the outcome of those decisions and the results over the course of a few years. That’s very powerful because someone’s going to ask you one day, can you tell me about a decision you made and how it turned out? And everything looks great on day one.” On AI adoption:“Generative AI tools that are available to us, they’re tools. They are a means to an end. You should experiment with them because you might discover that you can use it for something that you can have an outsized impact. You might be able to leverage this tool to create more value.” On leadership:“Your job as a leader, you’re making sure that there are people on the platform, there should be a team, that they are the right people, that they know where they’re going, that they’re going in the same direction... The leader is underneath of them supporting the team and building this stable platform.” On the LEGO Serious Play experience:“Fun. Yeah, challenging. It’s great. It’s good to have something... Keeps you occupied. Helps you think. It was actually delightful.” Where to Find Adam LinkedIn: Connect with Adam Tal on LinkedIn Herding Squirrels is a podcast where we dig into the nuts and bolts of teams, exploring what makes them work, what breaks them, and how to build something better. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com

    19 min
  8. Herding Squirrels Ep 13 w Oliver Gray

    10/06/2025

    Herding Squirrels Ep 13 w Oliver Gray

    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. Timestamps 00:00 - 01:50 - Introduction & Personal BuildOliver introduces himself and builds a model showing his life outside work: cooking with leftovers, playing squash, and hitting the occasional EDM event. 01:51 - 04:02 - Best Team ExperienceOliver builds a journey model showing how he took a team from dealing with inherited code chaos and demotivation to becoming high-performing through clarified mission, increased ownership, and self-direction. 04:03 - 09:08 - Nightmare Team ScenarioThe cautionary tale of a fixed-price consulting project gone wrong, complete with requirements gaps, access restrictions, and fundamental logic flaws that taught Oliver valuable lessons about software project structure. 09:09 - 13:13 - Leading Through UncertaintyOliver builds a model showing leadership as spinning between looking forward and looking back, emphasizing transparency, celebrating wins, and empathizing with team members through change. Discussion includes navigating AI adoption and the importance of product-focused engineers. 13:14 - 19:22 - Team Dynamics & InfluenceExploring psychological safety, the value of hybrid bonding moments, water cooler conversations, and how to create self-sufficient teams that don’t need constant management oversight. 19:23 - 22:25 - Final Build: Advice for New LeadersOliver’s final model emphasizes maintaining prioritized task lists, keeping eyes in all directions (up to leadership, sideways to peers, down to team), and building relationships across the company as gifts that inform better decisions. 22:26 - 22:47 - Wrap-Up & Where to Find Oliver Notable Quotes On Mission Development:“By developing the bottom-up and saying, this is what we think we should be doing. This is how we want to move that metric. This is what we think we’re good at, what we’re skilled at. That was how we managed to change the direction.” On Fixed-Price Projects:“If you’re ever going to do a fixed price project, then it has to be a fairly simple project with very well-known requirements, which in software is quite unusual.” On Empowering Teams:“I spoke to them about, I’d helped them sort of set the mission, but now I wanted the team to take over and be their own bosses. The team could be more nimble if they were driving what they were doing as a team themselves.” On Leadership Transition:“One of my engineers in the past joked that I was like their work counselor. The conversations I had with him were often like, you know, he would share his frustrations and I would empathize, sometimes provide ways out or alternatives, other times just say, yeah, that sucks.” On Self-Sufficient Teams:“Making your team become self-sufficient without you, right? So that you only have to spend a minimum amount of time with them, like helping them unblock things or when a project’s really important at the start of it or planning. But like the more self-sufficient they are, the more power you’ve given them, the better for you to look externally or from the balcony view.” On AI and Engineering:“What I told my engineers was that, you know, we all need to be using it, experimenting with it, seeing what it’s good for, potentially what it’s not good for. But from their perspective, if they’re product focused, which is a big thing for me, then that will definitely sort of ensure them for longer because it will take longer for AI to be both product focused and writing code.” Where to Find Oliver You can connect with Oliver Gray on LinkedIn, where he occasionally shares thoughts and ideas about engineering leadership and team building. Oliver is currently exploring new opportunities, so reach out if you have a great role for a leader who knows how to build self-directed, high-performing engineering teams. Ready to Transform Your Team? Your engineering team has untapped potential waiting to emerge. Your quiet developers might be your best strategic thinkers, but standard meetings don’t give them space to contribute. Want to discover what happens when every voice on your team actually gets heard? Book a LEGO® Serious Play® workshop with IN8 Create and watch your team dynamics transform. Visit in8create.com to learn more. Herding Squirrels is your podcast about modern teams, uncovering the nuts and bolts of what makes teams work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com

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About

Ever tried to get a group of squirrels to move in the same direction? Welcome to modern teamwork! Herding Squirrels is a podcast that explores the chaotic, wonderful, and sometimes maddening world of teams in our hyperconnected age. From Slack notifications pinging like acorns falling from a tree to the constant scatter of competing priorities, we dive into what makes teams tick. herdingsquirrels.substack.com

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  • Creator
    Created and Hosted by Brandon Wetzstein
  • Years Active
    2K
  • Episodes
    20
  • Rating
    Explicit
  • Copyright
    © Brandon Wetzstein
  • Show Website
    Herding Squirrels