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. Sep 25

    Being Liked Won't Carry Your Team Through Change. Trust Will.

    Dennis Richter is the Chief Business and People Officer at Fullscript, a billion-dollar healthcare platform, with prior leadership roles at Meta, Google, Deloitte, and 12 years in the Army. In this episode of Herding Squirrels, Dennis explains why people aren’t actually tired of change. They’re tired of change that feels disconnected, unfinished, or poorly explained. He shares why information travels down an organization far faster than it travels up, what a live town hall teaches that a scripted one can’t, and why the people holding your company together rarely show up as critical on the org chart. If you’re leading a team through change and wondering what isn’t reaching you, this conversation gives you practical ways to get the real story sooner. Guest Bio Dennis is an architect of high-growth organizations with 25 years of experience building and scaling global teams at the intersection of operations, technology, and people.He currently serves as Chief Business Officer at Fullscript, an intelligent healthcare platform pioneering whole-person care, where he owns the internal operating system of an enterprise that has recently surpassed $1 billion in annual revenue. Prior to this role, Dennis served as Chief People Officer, leading the company through significant growth and organizational evolution. Dennis’s career spans industry-defining companies and high-growth startups, including senior leadership roles at Google and Deloitte, as well as five years at Meta. At Meta, he served as Head of Global People Operations and as a Special Consultant to the Office of the CEO, partnering closely with senior leadership to scale complex global operations and drive enterprise-wide transformation. He has also served as Chief People Officer for the venture-backed startup Ad Hoc.His leadership philosophy was forged through 12 years of distinguished service in the U.S. Army, including work within Special Forces and multiple international commands. There, he developed a deep foundation in operational rigor, leadership development, and strategy under conditions of complexity and consequence.Today, Dennis brings this experience forward by mentoring veterans and military spouses, helping them translate their service into meaningful civilian careers and ensuring those who served have a clear and empowered path to success. Episode Highlights [00:01:02] Why every role is a people business, and the balance of giving more than you take [00:03:23] What makes a culture enduring: one that can scale without losing who you are [00:05:40] People aren’t tired of change. They’re tired of endless ambiguity. [00:08:11] The game of professional telephone, and why leaders need to circle back [00:13:29] Live Q&A versus pre-baked answers, and the power of “I’m not sure” [00:15:14] Individual contributors as the real influence without authority [00:22:02] Managers as the translation layer between tactical and strategic [00:25:10] Protect trust over optics Key Insights * Ambiguity Is the Real Fatigue: Your team can carry hard news. What wears them down is change that never gets explained, finished, or connected to what came before. Name what’s stopping, what’s different this time, and why it matters. (00:06:01) * Information Flows One Way: What you say travels down fast. What your team knows travels up slowly, if at all. If you aren’t actively pulling feedback back up, assume you’re missing most of it. (00:07:00) * Close the Loop in Cycles: Don’t trust that a message landed because your VPs delivered it. Check back in a week or two, ask where clarity fell short, adjust, and do it again. Two or three cycles builds muscle memory and trust. (00:08:30) * Defensiveness Ends the Conversation: The first time someone tells you your communication missed and you push back, you’ve taught them not to tell you again. Thank them, fix it, and follow up. (00:09:37) * Go Live, Not Scripted: A town hall with pre-screened questions and polished answers teaches your team that leaders never say “I don’t know.” Taking real-time questions, and admitting when you need to find out, makes it safe for everyone else to be honest too. (00:14:00) * Your Team Is Watching: Employees notice far more than leaders give them credit for. How you handle a hard question in front of the room shapes what people say about you at lunch. (00:18:53) * Map Relationships, Not Reporting Lines: Most companies run on human glue and spreadsheets. The people who carry institutional knowledge and quietly resolve conflict rarely look critical on the org chart. Find them before you need them. (00:23:17) Key Quotes “People carry hard things. What they cannot continue to carry is endless ambiguity.”Dennis “That information you thought traveled well rarely travels upward as fast as it travels down.”Dennis “They’re held together by human glue and spreadsheets.”Dennis “Protect trust over optics. Tell people the truth earlier than it feels comfortable.”Dennis Resources Mentioned * Fullscript: fullscript.com * Dennis Richter on LinkedIn * After action reviews (the Army practice Dennis applies to leading teams through change) About Herding Squirrels Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. Subscribe wherever you listen, and leave a review if this conversation was useful. 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

    Being Liked Won't Carry Your Team Through Change. Trust Will.

  2. Sep 23

    M&A Is Financial. Integration Is Human.

    Sachin Gulati is an M&A integration leader at HP with almost 14 years of deal experience across HP, Google, and management consulting. In this episode of Herding Squirrels, Sachin explains why M&A gets sold as a financial transaction but wins or loses as a human transition, and why even a good playbook only gets you 50 to 60 percent of the way there. He shares the three things he listens for on day one (fear, pride, and uncertainty) and the three habits that build employee trust during a merger. If you’re leading a team through an acquisition, a divestiture, or any big organizational change, you’ll leave with the conversations to stop avoiding and a way to make change painful but predictable. Guest Bio Sachin Gulati is currently an M&A Integration Leader at HP, with close to 14 years of experience in M&A spanning HP, Google, and management consulting. Throughout his career, he has led and advised on a broad range of acquisitions and divestitures, partnering with organizations and clients to navigate complex transactions, drive successful integration and separation, maximize value realization, and build scalable, repeatable processes and playbooks where needed. Find Sachin online: https://linkedin.com/in/sachin-gulati Episode Highlights [00:00:42] Why every deal is a new problem to solve, and why that keeps Sachin in M&A [00:01:31] Why a playbook covers only 50 to 60 percent of an integration, and when it covers 90 [00:05:13] Integration is a human transition, and what to listen for first: fear, pride, and uncertainty [00:09:04] How trust gets built during a merger through clarity, consistency, and follow through [00:12:20] The three conversations leaders avoid: people, power, and priorities [00:14:49] What first-time leaders miss about how different M&A is from any other program [00:17:29] The two roles AI plays in integration, productivity and decision making [00:19:59] One piece of advice for leaders: make the change painful but predictable Key Insights * Playbooks Get You Halfway: Buy a company like the last one and a playbook can cover 80 to 90 percent of the work. Change the deal type, the size, or the geography and it drops to 50 or 60. Use the playbook as a head start, then plan for the part it can’t cover. (00:01:31) * Integration Is Human: The deal is a financial transaction. The integration is a human transition, and that is what decides whether you get the value you paid for. (00:05:13) * Fear, Pride, Uncertainty: On day one, Sachin listens for three things. Where is the fear about roles, bosses, and jobs? Where is the pride, meaning what this team is good at and what you should protect? And where is the uncertainty, and how will you reduce it? Start there before you write a single announcement. (00:05:48) * Clarity, Consistency, Follow Through: Trust comes from telling people why the deal happened and what role they play, showing up again and again, and doing what you said you would do. A leadership session on day one followed by 180 days of silence doesn’t work. (00:09:04) * Say What You Don’t Know: You don’t need every answer. Tell people you haven’t thought about it, name the day you’ll come back to them, and then come back that day, even if all you have is what you’ve found so far. Let people ask the tough questions instead of talking them down. (00:10:24) * People, Power, Priorities: These are the three conversations leaders put off. Whose role might go? Who makes the final call when two leaders come together? What matters most? Sachin’s view is that priorities are priorities. Name the North Star early, phase the harder news, and accept that not everyone will get on board. (00:12:20) * Find Your Change Agents: Look for the well-respected people in the organization who believe in the change. They help guide others, and they double as your ears, telling you what uncertainty people are actually talking about. (00:20:54) * AI Tests Assumptions: AI already saves time on document review and diligence questions, so a target isn’t asked the same thing 100 times. Sachin thinks the bigger payoff is decision making, like giving it your strategy and business case and asking which assumptions have data behind them and which are guesses. (00:18:35) Key Quotes “M&A is often presented as a financial transaction, but integration is a human transition. And that’s what makes it win or lose.” Sachin “Integration is not a linear line. You have to adapt.” Sachin “You cannot have a leadership session at the start of the deal and then just don’t talk to them for 180 days. That doesn’t work.” Sachin Sachin’s advice for any leader putting people through major change: “Make sure it’s not painless, but predictable.” Sachin Where to Find Sachin * LinkedIn: https://linkedin.com/in/sachin-gulati About Herding Squirrels Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. New episodes drop every two weeks. Subscribe wherever you listen, and leave a review if this conversation was useful. 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

  3. Aug 6

    Why First-Time PE Acquisitions Fail

    Kit Lisle is the founder of operators.pe, the world’s leading peer community for private equity backed executives and operating partners, and a fractional operating partner with 30 years in the PE ecosystem. In this episode of Herding Squirrels, Kit breaks down why roughly 80 percent of founder led companies acquired by private equity for the first time go off the rails, and the five specific failure points that cause it. If you’re leading a team through a PE acquisition, a board transition, or any high stakes change, this conversation gives you the exact questions to ask and the timeline to ask them on. Guest Bio Kit Lisle runs operators.pe, a collaborative peer community he built from scratch after discovering no formal network existed for PE backed executives and operating partners. With three decades in the private equity ecosystem, he now works as a fractional operating partner, coach, and advisor, helping boards and management teams align after a first time acquisition. He’s spent his career aggregating best practices from experienced operators and sharing them in writing, on stage, and on podcasts like this one. Find Kit online: LinkedIn | kit@theoperators.pe Episode Highlights [00:00:10] Introducing Kit Lisle and operators.pe [00:02:38] Why Kit built the community himself after finding nothing like it existed [00:03:07] The 80 percent failure rate when PE acquires a founder led company for the first time [00:04:59] The “wait and see” mindset that sets the failure in motion [00:06:50] The five questions every management team needs answered: who, why, when, where, what [00:09:00] Fixing the 80 percent with onboarding and organizational due diligence in the first 100 days [00:10:22] The five risk factors, walked through one by one [00:15:42] Why the first 100 days should target two quick, visible wins [00:21:50] Kit’s advice to any leader guiding a team through change Key Insights * The wait and see approach backfires: Most PE firms default to watching quietly for a year before acting, hoping to sort out who’s swimming and who’s sinking. Kit argues this is simply inefficient, because it leaves capable people without the tools, like the investment thesis and value creation plan, they need to actually do their jobs. (00:04:59) * Five questions close the information gap: Management teams stepping into board oversight for the first time should be asking why the deal happened, who holds which decision rights, when the exit is targeted, where the company stands against the plan, and what leadership style the moment calls for. Most of this never gets asked because nobody’s used to a board relationship. (00:06:50) * Misalignment starts inside the room: A CRO chasing price increases, a CFO cutting costs, and a CEO chasing new logos can each be doing their job well and still be rowing the canoe in three different directions. Alignment has to happen internally, with the board, and with outside stakeholders, not just at the top. (00:10:22) * “Line of sight” breaks down in the middle: A CEO can hold a clear town hall and still lose the message by the time it reaches a plant manager or regional sales VP. Deployment isn’t complete until the person furthest from the boardroom understands what’s changing, what’s stopping, and what’s in it for them. (00:11:43) * South to north feedback takes repetition, not a memo: CEOs often assume they have an open channel for hearing what isn’t working. In practice it can take a leader saying “tell me what’s broken” three, four, five times before people actually believe it and start talking. (00:13:12) * The first 100 days needs visible wins: Kit’s benchmark for early success isn’t a strategy document, it’s small, tangible results the CEO can point to internally and with the board to build credibility fast. (00:15:42) * A good board meeting isn’t a report, it’s a conversation: Incumbent management teams often walk into board meetings expecting to explain themselves or ask permission. Kit reframes the healthy version: reporting happens beforehand, and the meeting itself is for genuine, candid collaboration on decisions that are still unresolved. (00:15:42) * Willingness to learn is the real filter: Past the first test of capability, the people who succeed after an acquisition are the ones who ask for feedback with humility instead of waiting for permission. Kit says demonstrating that genuine interest in getting better is half the battle. (00:20:34) Key Quotes * “A good board meeting is not a good readout or report. It’s not about getting permission. It’s not about sharing something that you’re doing. It’s really an intellectually stimulating conversation.” * “If we don’t have alignment, we don’t have good governance and understanding of decision rights or deployment or accountability or the appropriate leadership style, value creation is simply not going to happen.” * theoperators.pe — Kit Lyle’s peer community for PE backed executives and operating partners * Kit Lisle on LinkedIn * Email: kit@theoperators.pe About Herding Squirrels Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. Subscribe wherever you listen, and leave a review if this conversation was useful. 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

  4. Jun 12

    Why M&A Integrations Fail the People They Need Most

    Lucas Liu is the Managing Director at Risecor, a boutique consulting firm specializing in M&A integration, carve-outs, exit readiness, and AI strategy for private equity firms and their portfolio companies. In this episode of Herding Squirrels, Lucas breaks down why so many integrations fall apart at the people level and what leaders can actually do about it before the cracks appear. If you’re navigating an acquisition, advising one, or leading a team through serious organizational change, this conversation is direct and practical. Guest Bio Lucas Liu is the Managing Director at Risecor, a boutique consulting firm focused on M&A integration and carve-outs, exit readiness, process optimization, data analytics, pricing strategy, and AI. He works primarily with private equity firms and their portfolio companies across middle market and enterprise transactions. Lucas has been on both sides of the integration table, advising the acquiring company and the company being sold. Find Lucas online: risecor.com Episode Highlights [00:02:01] Why communication breakdown is the most consistent failure in M&A integrations [00:05:30] "In the absence of fact, rumor becomes fact" — the virtual water cooler problem [00:07:59] Why integration leaders fail at communication (it's not bad intent, it's overload) [00:15:51] How to map power dynamics before close to avoid blind spots post-close [00:22:46] The influencer strategy: finding the people who hold the informal org chart [00:26:12] How AI is showing up in due diligence and integration management today [00:28:18] Why most "AI layoffs" are actually COVID overhiring cover stories Key Insights * Overcommunicate, always: The number one failure Lucas sees across integrations is not a lack of competence but a lack of consistent communication. People who aren’t directly involved in the integration still need to know what’s happening, why it’s happening, and where things stand. You will never get complaints about too much information. You will always get complaints about silence. (00:04:16) * Rumor fills the void: When leaders go quiet, teams don’t go quiet. They speculate. The Slack channel you’re not in becomes the actual water cooler, and what gets said there is almost always worse than the truth. A weekly email, an updated FAQ page, a short all-hands update — these aren’t optional extras, they’re retention tools. (00:05:30) * First-time integration leaders are the hidden risk: Many of the people running integrations have never done one before. They’re also trying to keep their normal work moving, figuring out the new power structure, and trying to impress people whose names they barely know yet. Communication is the first thing that gets dropped when time runs out. That’s a leadership architecture problem, not a personal one. (00:07:59) * Map the power dynamics before close: Lucas goes in early specifically to understand who the new CEO is, what their style is, which team members from the acquired company will be retained in meaningful roles, and where the fault lines are likely to form. The more of that you understand before day one, the better positioned you are to move fast without breaking trust. (00:15:51) * The influencer is rarely the most senior person: Lucas asks every functional head the same question during due diligence: who on your team has the pulse of the organization, even if they’re not a manager? These are the people others informally look to, the ones who calm rooms or quietly derail initiatives. Knowing who they are, including them early, and tying their effort to visible rewards is one of the most underused retention levers in integration work. (00:22:46) * AI is a tool for integration management, not a headcount replacement: The practical use of AI right now in M&A is tracking integration plans, surfacing late deliverables, and automating status reports. It’s useful. But Lucas is clear: AI isn’t accountable. When something goes wrong, someone needs to own it, and that’s still a human. (00:27:43) * Most AI layoffs aren’t really about AI: Lucas’s read is that many companies framing layoffs as AI-driven efficiency are actually unwinding COVID-era overhiring. “AI” is the cover that gets you credit instead of criticism. The companies using AI well are using it to free up their people to do higher-value work, not to get rid of them. (00:28:18) Key Quotes “You’ll never get complaints about too much information, but you’ll always get complaints about I have no idea what’s going on.” — Lucas “In the absence of fact, rumor becomes fact” — Lucas “You ask the manager what they do and he’ll tell you five things. You ask the person what they do, they’ll tell you seven things, and only three of them match what the manager told you.” — Lucas “Change is about people. Regardless of how much technology is being used, how AI is being brought in — at the end of the day, it’s the people that are going to make it successful or not.” — Lucas Resources Mentioned * Risecor — risecor.com * Lucas Liu on LinkedIn 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

    Why M&A Integrations Fail the People They Need Most

  5. Jun 2

    What Diligence Misses When the Team Can't Name How the Business Works

    Andrew Matney is a finance, strategy, and M&A operator who has seen transactions from nearly every angle — lender, advisor, investor, and operator. In this episode of Herding Squirrels, he shares what gets missed when everyone is on their best behavior before the close, and why the real operating system of a founder-led business lives in decisions, not documents. If you’re navigating a post-close integration or thinking about how to prep a company for acquisition, this conversation will change what you look for. Guest Bio Andrew Matney is a finance, strategy, and M&A operator whose career has followed a non-traditional path across commercial banking, investment banking, private equity, and technology-enabled industrials. He is currently a Founding Team Member, Chief of Staff, and Head of M&A at America’s Innovation Corporation (”AIC”), where he works at the intersection of acquisitions, operations, and the U.S. manufacturing base supporting the robotics and physical AI supply chain. Prior to AIC, Andrew was a Principal at Altus Capital Partners, focused on acquiring and building lower-middle-market industrial and manufacturing businesses. Earlier in his career, he held M&A advisory roles at Lincoln International and Park Sutton Advisors, and began his finance career in commercial banking at Wells Fargo and Capital Bank. Across these roles, Andrew has seen transactions from nearly every angle — lender, advisor, investor, board observer, and operator — giving him a practical perspective on what makes deals work after the close. His perspective centers on the human side of transactions: how founder-led companies actually make decisions, how trust is built during periods of change, and how to modernize a business without flattening what made it successful in the first place. Find Andrew online: LinkedIn Episode Highlights [00:00:47] Reading people under pressure: what acting, banking, and PE teach you that the other two don’t [00:02:05] What curated data rooms and management presentations can’t tell you [00:04:06] Where the operating system lives in a founder-led business vs. a carve-out or PE add-on [00:07:43] The risk of professionalizing away exactly what made the business worth buying [00:10:33] The three questions that reveal whether a founder truly has a number two [00:15:33] What post-close cracks actually look like and why diligence doesn’t catch them [00:17:46] Why the hardest thing to align on isn’t purchase price — it’s decision rights [00:21:17] One piece of advice for founders preparing to sell: start the people conversation before the deal forces it Key Insights Curated packages lie by omission. Everything in a VDR and management presentation was put there on purpose. Reading a team means getting past the curated version and into what actually motivates, scares, and excites the people running the business. That’s the signal that predicts how a transition will land. (00:02:05) The operating system lives in the founder’s head. In founder-led lower middle market companies, a lot of institutional knowledge is not codified. Which customer pays slowly but is worth keeping. Which supplier needs a call, not an email. Which margin issue is real versus noise. Integration can’t start with a playbook. It has to start with: show me how this place actually works. (00:04:06) Professionalizing too fast destroys value. Move too quickly and you run the risk of standardizing away the exact thing that made the business valuable. The goal isn’t to flatten a company into a corporate template — it’s to preserve what works and make it teachable. (00:07:43) Founder gravity is not a process. Post-close, you discover what was real process versus what happened because the founder was in the room. That distinction matters enormously for who owns daily decisions once the founder steps back. (00:15:50) Decision rights cause more friction than purchase price. Everyone can agree in principle that the founder will keep running things. The collision happens the first time a real decision has to be made — who approves a key hire, who talks to the biggest customer, who owns pricing. A working agreement before close that names those moments explicitly prevents a lot of post-close pain. (00:17:46) Most tension is ambiguity, not bad intention. The friction that shows up at month three or four is usually not because someone is acting in bad faith. It’s because both sides thought the agreement meant something slightly different. The antidote is specificity before the decision arrives. (00:19:09) Prepare the team before the deal forces the conversation. Founders spend enormous energy cleaning financials and telling the growth story. The team is what carries the business after close. If the first time key employees understand the founder’s thinking is the day the deal is announced, you’ve already created unnecessary anxiety. (00:21:17) Key Quotes “In a deal room, everyone has a role. The founder wants certainty and respect. The buyer wants truth and downside protection. The banker wants momentum. The management team may be wondering whether they still have jobs.” — Andrew “Integration can’t start with ‘here’s our playbook.’ It has to start with ‘show me how this place actually works.’” — Andrew “The red flag is not a founder who’s tired. Most founders are tired by the time they sell. The red flag is a founder who wants the authority of staying without the responsibility of changing how the company makes decisions.” — Andrew “A lot of what diligence misses is not because people are hiding things. It’s because they don’t really have language for how the business works.” — Andrew Resources Mentioned America’s Innovation Corporation — Andrew’s current company, focused on acquisitions in U.S. manufacturing, robotics, and physical AI Altus Capital Partners — lower-middle-market industrial and manufacturing private equity firm where Andrew was previously a Principal Lincoln International — M&A advisory firm where Andrew held an earlier advisory role Park Sutton Advisors — M&A advisory firm where Andrew held an earlier advisory role Andrew Matney on LinkedIn Concepts discussed: decision rights frameworks, working agreements pre-close, key man risk, founder gravity, institutional knowledge transfer Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. Subscribe wherever you listen, and leave a review if this conversation was useful. 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

    What Diligence Misses When the Team Can't Name How the Business Works

  6. May 27

    Resistance Is Data and What That Means for M&A Leaders

    Guest Bio Kamran Jahanshahi is the President and Founder of PeakPoint Consulting, where he helps organizations navigate business transformation, operational excellence, digital strategy, AI adoption, and change management. He brings more than 25 years of leadership experience across Citibank, MetLife, Walgreens Boots Alliance, and his independent consulting work, with deep experience in M&A integration, target operating model design, Lean Management Systems, finance and technology transformation, global operations, and large-scale system implementations. Kamran has worked closely with CEOs, CFOs, CIOs, and senior leadership teams to turn strategy into execution, including shaping the target operating model for a $15.5 billion acquisition across 60 countries. Recently he has been writing and advising on AI adoption, including the need for AI operating models and Centers of Excellence that help organizations move beyond pilots toward redesigned work, stronger governance, and measurable business value. Outside of consulting, Kamran is an endurance athlete and active in nonprofit boards focused on expanding access to healthcare, education, jobs, and opportunity. Find Kamran online: https://www.linkedin.com/in/kamran-jahanshahi/ | peakpointconsulting.net Episode Highlights [00:00:50] How a front-row seat to the Citi-Travelers merger turned Kamran into a change junkie for life [00:06:03] What it took to cut M&A integration cycle time from 24 months to 12 at Citibank Cards [00:08:35] The integration muscles most organizations don’t build until it’s too late [00:13:10] Why the operating model — people, processes, technology, governance, location — has to anchor every integration plan [00:17:09] Three leadership anchors that determine whether people actually follow during an integration: clarity, credibility, and line of sight [00:21:18] How silence and ambiguity create water cooler rumors that take on a life of their own [00:25:13] Why resistance to change is data, not a problem, and the pre-mortem practice that surfaces it before it costs you Key Insights * Integration fails at the connection, not the strategy. Deals rarely fall apart because the strategy was wrong. They fail when people cannot draw a line from the strategy to what they are being asked to do every day. Kamran saw this firsthand at Citi when two conflicting messages — cost cutting and customer experience — ran simultaneously with no integrated messaging to reconcile them. (00:03:03) * Build the muscles before you need them. Companies that treat acquisition as a strategic growth lever need to have playbooks, process maps, and identified leaders ready before a deal lands. The organizations that scramble to stand up an integration team after close are already behind. (00:11:03) * The operating model is the integration. People, processes, technology, governance, and location — these five elements are what actually has to combine. Knowing your target operating model before you close is what makes everything else executable. (00:13:10) * Clarity, credibility, and line of sight. These are the three things people need from leadership during an integration. Credibility in particular gets destroyed fast when what leaders say and what they measure are different things. People watch what you do, not what you say. (00:17:09) * Silence is not safety, it’s a rumor factory. When people don’t have answers about their jobs and their future, they fill the gap. Anxiety-driven speculation takes on its own life and pulls energy away from the work that needs to happen. (00:21:18) * Resistance is data. When people push back against change, they are not being difficult. They are signaling something they don’t know, don’t understand, or are afraid of losing. Treating that signal as information rather than resistance changes how you respond to it. (00:25:13) * The pre-mortem creates safety to say the hard thing. By asking teams to imagine the integration has already failed and to work backward, leaders get access to objections and fears that would never surface in a normal meeting. And it should not be a one-time exercise. (00:26:05) Key Quotes “Integration is not just a project plan. It’s truly a leadership test.” — Kamran “The process, the tools are easy to manage. You can redesign the process, you can bring in the best tools, but if you don’t get the people’s buy-in, and if the people don’t understand why you’re doing this, it doesn’t work.” — Kamran “To me, resistance to any change is data. It’s information.” — Kamran “Those anxiety-driven questions lead into water cooler rumors that then take their own life. And you find yourself managing a very unfounded set of stories instead of focusing on the job that needs to get done.” — Kamran Resources Mentioned * Peak Point Consulting: peakpointconsulting.net * Kamran on LinkedIn * Pre-mortem methodology (Gary Klein) — referenced as a tool for surfacing team fears before integration risk materializes * The MUM Effect — referenced by Brandon; the psychological tendency to withhold bad news, amplified by hierarchy About Herding Squirrels Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. New episodes drop every two weeks. Subscribe wherever you listen, and leave a review if this conversation was useful. 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

    Resistance Is Data and What That Means for M&A Leaders

  7. May 20

    Why Your AI Pilots Keep Stalling and What to Build Instead

    Louie Celiberti is the founder of E27 Technology Solutions and spent over 15 years at Guggenheim Partners leading enterprise data and AI transformation at scale. In this episode of Herding Squirrels, he returns to share why most AI pilots fail not because of the technology but because of how organizations approach the work — and what a more deliberate, architecture-first model actually looks like. If your team is drowning in AI experiments that never seem to graduate into something real, this conversation will give you a clearer picture of what’s getting in the way and how to fix it. About Louie Louie Celiberti is the founder of E27 Technology Solutions and former Managing Director and Head of Software and Data Engineering at Guggenheim Partners, where he spent over 15 years leading enterprise data, cloud, and digital transformations. He focuses on helping organizations move beyond AI pilots through a pragmatic, architecture-first approach that balances immediate business value with long-term scalability. His work centers on designing modular, vendor-agnostic platforms and investment-optimized roadmaps that allow organizations to reuse capabilities and evolve their AI and data strategy over time. Find Louie online: e27technologysolutions.io Episode Highlights [00:01:00] The CTO shift from driver of innovation to shepherd of innovation [00:03:25] What engineering discipline gives technologists that most business teams still lack [00:08:13] The mutual mentorship model and why it makes cross-functional AI work stick [00:12:00] Slowing down to speed up: the thin-slice approach to AI implementation [00:18:06] Meeting people where they are: how emotional intelligence shapes AI adoption in resistant organizations [00:21:12] Why collaboration isn’t optional when AI moves this fast [00:23:45] The real reason AI pilots stall: hubris, missing context, and skipping the ecosystem Key Insights * The shepherd shift: The CTO role is no longer about generating innovation from the top — it is about harnessing innovation that now originates in the business. The business has always had the context. Engineers bring the discipline to make it scalable and sustainable. (00:01:00) * Engineering discipline is a cross-functional muscle: Technologists have spent decades sitting across every business unit, learning to see how things connect. That pattern recognition — the ability to spot reusability, shared risk, and downstream impact — is something most business teams have never been forced to develop. (00:03:25) * Mutual mentorship as the change mechanism: When everyone gets a turn to share what they know, they also become more willing to listen. That dynamic creates vested interest. People who contributed to an idea will advocate for it. That is not a soft concept — it is how you move faster without losing people. (00:08:13) * Thin slices, not big bets: The instinct under pressure is to find the one transformational use case and commit. What actually works is small, multi-dimensional starting points that touch multiple perspectives at once. Narrow enough to move quickly, wide enough to represent the whole system. (00:12:00) * Skills versus talents: Skills are learnable in isolation — tools, certifications, frameworks. Talents are different. Emotional intelligence, the ability to connect dots across disconnected conversations, genuine listening — those are the things that determine whether an AI program actually takes root. (00:21:12) * The ecosystem mistake: Organizations are treating pilots like proof of concept when they should be treating them like the foundation of a capability library. Spin up five or six use cases, extract the reusable components, and you have something to build from. Learn the lesson during the pilot, not after. (00:25:01) * Progress has to be felt, not counted: The people pushing hardest for speed are usually the ones farthest from the work. The fix is not more status reports — it is framing progress in terms that connect directly to what that audience cares about, especially revenue and risk. (00:16:24) Key Quotes “Being quick is great. Being deliberate and methodical is even better — and none of those things are slow.” — Louie “The smartest people will recognize what they don’t know once they start talking to everybody.” — Louie “Skills are things you can obtain in isolation. Talents are the less tangible characteristics that allow individuals and teams to succeed.” — Louie “Assume it’s going to work. It will work. The real question now is how do you implement so that you can build other things and make it sustainable.” — Louie Resources Mentioned * E27 Technology Solutions — Louie’s firm: e27technologysolutions.io * Claude Code and Cursor — AI coding tools referenced for rapid prototype generation * Diffusion of Innovations curve — Referenced in discussion of AI adoption across organizational profiles (innovators, early majority, laggards) About Herding Squirrels Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. New episodes drop every two weeks. Subscribe wherever you listen, and leave a review if this conversation was useful. 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

    Why Your AI Pilots Keep Stalling and What to Build Instead

  8. May 4

    Herding Squirrels Ep 23 w Stephen Szypulski

    Post Body Stephen Szypulski leads post-acquisition integration at Fitch Learning, part of Fitch Group and Hearst Corporation, where the business serves more than 100,000 learners across over 100 countries. In this episode of Herding Squirrels, he walks through why so many M&A deals lose value after close, what actually breaks first when an integration plan meets reality, and why the work of integration is fundamentally about shepherding velocity without pushing the organization into shock. If you are leading change, integrating teams after an acquisition, or running an AI rollout that is starting to look like a merger, this conversation will give you a clearer way to think about people, culture, and the parts of the deal that never show up in the model. Guest Bio Stephen Szypulski is Head of Integration and Strategic Operations for Fitch Learning, part of Fitch Group and the Hearst Corporation. He leads post-acquisition integration for a global business serving more than 100,000 learners across 100+ countries, using integration as a driver of business transformation and long-term value creation. Before Fitch, Stephen held senior leadership roles at Bank of New York and Goldman Sachs, working on acquisitions including GreenSky and United Capital (RIA). He serves as an operating partner to management teams, integrating organizations, aligning commercial priorities, enabling technology, and building operating models that scale. Find Stephen online: LinkedIn Episode Highlights [00:00:50] How a politics major ended up running M&A integration at Goldman Sachs and why integrations are the impetus for transformation [00:02:18] What leaders get wrong in the first 72 hours after a deal closes [00:04:23] Why human capital challenges and commercial distraction surface immediately post-close and never appear in the deal model [00:05:52] The art of velocity, or how fast you can integrate without pushing the organization into shock [00:06:18] What you can actually learn about culture from behind the diligence wall before a deal closes [00:13:32] Why culture cannot be created overnight and how phased integration earns it instead [00:21:57] Why roughly 70% of M&A activity misses its targets and what that says about how integration as a discipline has evolved [00:23:47] What AI does to the integration playbook and why humans become orchestrators of systems, not executors of steps Key Insights * Integration is structure, not a checklist. The most useful reframe in the conversation. Integration is bringing structure to chaos. It is guardrails, decision frameworks, and the work of shepherding velocity. The fifty boxes you can tick are scaffolding, not the job. (00:11:59) * The deal model never accounts for commercial distraction. Customer-facing teams slow down after close. Not because they want to. Because roles shift, products change, and people genuinely do not know who they report to or what to sell. Plan for the slowdown instead of pretending it will not happen. (00:05:27) * Culture is hard to measure from behind the diligence wall. You can read history, financials, attrition, and how an organization has handled past change. What you cannot see until after close is how a team really escalates, collaborates, and absorbs shock. Bake that uncertainty into your timeline. (00:06:18) * Velocity is the real lever. The job is to move fast enough to realize the value of the deal without pushing the organization into a state of shock that becomes disorder. Most timelines are too clean and too aggressive at the same time. (00:05:52) * Get clear about what you do not know. It is okay to enter the integration with unknowns. Build allowance into the timeline to do real diligence after close, ask good questions, and avoid making decisions that cannot be unwound. (00:17:04) * Retention is part contract and part signal. There are the structured tools, retention bonuses, role continuity, and contractual incentives. There are also the softer signals. Are you showing the people you acquired that you actually value them and the knowledge they carry. Both matter and one without the other tends to leak value. (00:18:50) * Integration work is relationship work. It touches every function and every geography, but at its core it is about how you build trust across cultures, translate between the C-suite and the frontline, and align teams around a common goal. The technical understanding matters. The relationship work is what makes it land. (00:20:41) * AI is the next integration. Bringing AI into an organization is integration work too. Systems, data, workflows, governance, and decision-making all have to come together. Going forward, the role of the integration leader becomes designing and governing those systems rather than executing each step manually, function by function. (00:24:42) Key Quotes “Integration is really about bringing structure to chaos. It is creating guardrails. It is creating decision frameworks. It is shepherding the velocity of the organization.” — Stephen “How do you move fast enough to realize the deal without pushing the organization into too much shock that it becomes disorder?” — Stephen “You have a good idea going into the deal as a part of the diligence phase. But you never really know what you get until you get to the other side.” — Stephen “It is okay to have integration unknowns that get figured out along the way.” — Stephen Resources Mentioned * BCG research on M&A failure rates (~70% of deals fall short of stated targets) * The integration-as-private-equity-operating-partner model * Stephen on LinkedIn — linkedin.com/in/stephenszypulski About Herding Squirrels Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. New episodes drop every two weeks. Subscribe wherever you listen, and leave a review if this conversation was useful. 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

    Herding Squirrels Ep 23 w Stephen Szypulski
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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

Information

  • Creator
    Created and Hosted by Brandon Wetzstein
  • Years Active
    2025 - 2026
  • Episodes
    30
  • Rating
    Explicit
  • Copyright
    © Brandon Wetzstein
  • Show Website
    Herding Squirrels