The CTO Compass

Why Dropping AI Into a Broken Process Makes Everything Worse ft. Mike Toguchi

Most technology leaders start by looking at the tool. Mike Toguchi, Chief Strategy Officer at Tectonic, argues that is the wrong beginning. If you drop AI into a broken process, you don't fix the problem, you only accelerate the failure. Mike joins the conversation to discuss why the most critical technology decisions often happen outside the engineering team and how to build systems that scale without drowning in technical debt. Mike brings a unique perspective as a strategist who studied government and politics rather than computer science. Having spent 23 years evolving with the same company, he has seen the transition from simple web digitization to the current age of AI. We talk about the "bad cop" role a partner must play in forcing standardization across departments and why the biggest hurdle to digital transformation is rarely the code, but the legacy silos and people who protect them. We also dive into the reality of AI governance and policy. Mike shares how his team navigates the tension between rapid innovation and protected data in high-stakes environments like university disability services. It is a discussion about judgment, critical thinking, and why the next two years will separate the leaders who aggressively pursue change from those who simply try to limp along. ABOUT MIKE Michael "Mike" Toguchi is the Chief Strategy Officer at Tectonic, formerly eResources, where he leads platform direction for application management systems that streamline complex processes like scholarships, grants, admissions, and accessibility services. With over 25 years of experience driving digital transformation for universities, non-profits, foundations, and associations, Michael specializes in simplifying internal workflows to help mission-driven teams reduce manual work, scale sustainably, and strengthen compliance. His work powers organizations including Stanford, UC Davis, PG&E, the Roddenberry Foundation, and Google’s Certified Innovator Program. At the core of his mission is a commitment to building technology that enables teams to focus less on managing systems—and more on delivering meaningful impact. CHAPTERS 00:00 Politics to Technology?!??! 06:08 What is Tectonic? 11:55 Ad 12:27 23 Years of Growth and Change 15:41 The Value of People 19:51 Customization Accommodation 26:44 Ad 26:55 Who Makes Technology Decisions? 28:25 AI Implementation and AI Policy Issues 36:36 The Future of Tech WHERE TO FIND MIKE * Website: https://www.teamtectonic.com/ * LinkedIn: https://www.linkedin.com/in/miketoguchi/

3 Critical Career Mistakes Engineering Leaders Make ft. Limor Bergman Gross

This episode focuses on the transition from technical execution to organizational impact. Limor Bergman Gross shares how many engineering managers get stuck because they focus solely on being good at their jobs. She explains that promotion to director or VP levels requires a shift in focus. It is no longer about how well you code or manage a sprint, but about how well the organization knows your impact. The conversation explores the "trust gap," where leaders mistakenly believe their direct manager is the only one who needs to see their value. Limor and Mark discuss the necessity of building strategic relationships across the company. They provide a framework for stakeholder management that relies on curiosity and solving business problems rather than internal politics. This approach helps technical leaders gain the visibility needed for executive roles. Finally, the discussion covers the practicalities of leadership like delegating effectively and giving direct feedback. Limor highlights the "busy trap" where leaders fill their schedules with low-impact tasks to feel productive. She offers strategies for pushing back on non-essential requests to create space for strategy. The episode concludes with advice on using the Radical Candor framework to build high-performing teams through clear, empathetic communication. ABOUT LIMOR Limor Bergman Gross is a former Director of Engineering with over 20 years of experience across software engineering, engineering management, and organizational leadership. She has led teams through growth, scaling pressure, and complex delivery environments, working closely with CTOs and senior executives to align technology, people, and business priorities. Known early in her career as the “reliable leader” and escalation point, Limor learned firsthand how high-performing leaders can unintentionally become bottlenecks at scale. Today, she works as an executive leadership coach with senior engineering leaders and CTO-adjacent roles, helping them transition from hands-on decision-makers to strategic leaders who build teams that think, decide, and execute independently. Her work focuses on decision-making, ownership, leadership culture, and the real trade-offs tech leaders face as they move from execution to executive impact. CHAPTERS 00:00 Software Engineer to Leadership 06:33 Getting Promoted 14:39 Ad 15:11 What are You Busy With? 20:26 How to Give Feedback 22:53 Female Engineers! 24:50 Coaching The Executives 29:08 Ad 29:19 Getting Unstuck 36:54 Working with Different People 40:45 What is Your Impact? WHERE TO FIND LIMOR • Website: https://limorbergman.com/podcast/ • LinkedIn: https://www.linkedin.com/in/limorbergman/ • Instagram: https://instagram.com/limorbergman • YouTube: https://www.youtube.com/@LimorBergman

Your AI Strategy Will Fail for the Same Reason Your Last ERP Did ft. Abhijit Verekar

Most large-scale technology projects don't fail because the software is broken; they fail because the incentives are misaligned long before the first line of code is written. AV, founder of Avira Advisors and author of Start at Zero, joins Mark Wormgoor to discuss why massive ERP implementations, like the Birmingham City Council’s £200 million disaster spiral out of control and how tech leaders can prevent the same history from repeating itself with AI. AV argues that the "abusive" nature of traditional consulting often stems from a lack of "Phase Zero" preparation. Organizations frequently jump into software selection and vendor RFPs without understanding their own internal processes, political buy-in, or desired outcomes. By the time an implementation partner is on-site, the customer has already lost their leverage, leading to endless change orders and "fluffy" risk registers where every red flag is painted green. As we move into the age of AI, AV sees enterprises making the exact same mistakes: chasing shiny "agentic" products before they have established data sovereignty or governance. This conversation serves as a pressure-test for any leader about to sign off on a major digital transformation. AV shares how to reclaim ownership of your data, align consultant incentives with business value, and why the future of consulting belongs to those who can bridge the gap between AI-native thinking and human judgment. Key Takeaways • Success in high-stakes projects is determined before the RFP; spend time documenting processes and securing political buy-in before talking to vendors. • Traditional consulting can become "abusive" when vendors dictate timelines and products based on their own sales targets rather than the client's actual needs. • In the AI era, leaders must ensure they own their data and can move it between third-party tools rather than being locked into a single SaaS provider's ecosystem. • Like ERP, AI adoption fails when it is treated as a product-first purchase instead of a business-process transformation requiring clean data and human oversight. • The traditional billable-hour model is collapsing; value now lies in senior-level judgment, "blameability," and the ability to integrate AI "Lego bricks" into delivery. • While AI can automate the "grunt work" of deliverables, final accountability must always rest with a seasoned human expert who carries the risk of the decision. ABOUT AV AV is the CEO of Avero Advisors, a government consulting firm he built from zero to $7.5 million over the last ten years. He's spent two decades helping state and local agencies navigate ERP implementations, AI strategy, and digital transformation, and he's been in the room for a majority of these engagements. He's currently writing a book called Start at Zero and rebuilding his firm around AI agents that handle everything from business development to content production and delivery. Before Avero, AV spent a decade inside the traditional consulting world learning how the machine worked before deciding to build something different. Avero operates as the buyer's agent for government agencies, sitting on their side of the table instead of the vendor's. The firm has grown to a team of around 40 to 50 people, including a Global Innovations Center. Outside of consulting, AV is an active investor. He's invested in BSG Hospitality and Market Square Ventures, applying the same builder's mindset to opportunities outside of govtech. When he's not running the firm or writing, you'll probably find him on a motorcycle. He's an avid rider who uses long rides the same way some people use meditation: to think, decompress, and come back with clarity. AV brings a rare combination to any conversation: deep technical credibility in government technology, real experience bootstrapping and scaling a services business, and an honest willingness to talk about what he got wrong along the way. He's not going to give your listeners a sales pitch. He's going to give them something useful. CHAPTERS 00:00 When Consulting Becomes Abusive 08:46 Laying Down the Foundation! 11:43 Ad 12:14 Private Companies vs Private Sectors 16:51 Excited AI Implementation 20:26 AI's Impact 27:09 Ad 27:20 How do You see the Future? 32:29 Starting Out Today! WHERE TO FIND AV • Website: www.averoadvisors.com • LinkedIn: https://linkedin.com/in/verekar/ • Instagram: https://www.instagram.com/verekar/ • Twitter: https://x.com/AbhijitVerekar AV’s Book https://www.amazon.com/Start-Zero-Leading-Stakes-Modernization/dp/B0GZFQLDJ3 [https://www.amazon.com/Start-Zero-Leading-Stakes-Modernization/dp/B0GZFQLDJ3]

Why Organizational Change Fails: The Hidden Politics and Self-Interest Killing Your Transformation ft. Bud Caddell

Mark Wormgoor sits down with Bud Caddell, founder of NOBL, to explore the human friction that often stalls massive technology initiatives. Bud shares his transition from a software developer to a change management expert, triggered by witnessing "shiny" innovation projects collapse under the weight of organizational politics and conflicting incentives. The conversation dives deep into why many digital transformations are dead on arrival, often due to manufactured urgency and a lack of focus that spreads leadership teams too thin. The discussion shifts toward practical strategies for overcoming these barriers, with Bud advocating for a "piecemeal" approach to organizational change. Rather than following a rigid, 200-slide consultant deck, he suggests using "safe to fail" experiments to surface hidden politics and resistance early in the process. They also tackle the evolving role of the CTO in the age of AI, discussing how tech leaders are gaining unprecedented power but risking their internal relationships by failing to build empathy with the teams impacted by these rapid shifts. Finally, Bud addresses the growing issue of organizational cynicism and the "trust gap" between leaders and employees. He argues that the antidote to mass change fatigue isn't better technology, but radical honesty and transparency regarding what an organization can and cannot control. The episode concludes with a look at how leaders can build resilience by moving away from purely visionary "Steve Jobs" personas toward a more grounded, transactional, and honest theory of leadership. Key Takeaways • Many projects fail not because of the tech, but because "manufactured urgency" exhausts the organization’s attention span before the change can take root. • Avoid "rip the band-aid off" transitions; instead, use small, iterative experiments to discover where political resistance and sabotage actually live. • Apply agile experimentation to cultural rituals and habits, but use traditional stakeholder mapping and steering committees for high-risk reorgs or core system implementations. • Recognize that most "sabotage" is actually people protecting their teams or resources; breaking through requires negotiating power and resources rather than just fighting for a meritocracy. • As AI pushes more power toward the CTO, be careful not to burn bridges with other executives; success depends on building a coalition, not just wielding technical influence. • To reduce change fatigue, stop over-promising; be transparent with employees about layoffs, market pressures, and the specific limitations of your control. ABOUT BUD Bud Caddell is the Founder and CEO of NOBL, a global transformation consultancy reshaping how organizations adapt to change. Since 2014, he has led more than 120 engagements across five continents, helping companies in more than 20 industries, including Nike, Ford, CNN, and HBO, navigate disruption, repair dysfunctional cultures, and build resilient teams. Recognized by The Guardian as one of the “strategists to watch” and named one of Business Insider’s “most creative people under 30,” Bud’s work has been featured in The New York Times, The Wall Street Journal, Forbes, and AdAge. Before launching NOBL, he was a Partner at Undercurrent and served as SVP of Digital Strategy and Innovation at Deutsch LA. Bud Caddell is a distinguished speaker and guest, having delivered keynote addresses at SXSW, TEDx, and the Reuters Strategic Marketing Conference. His core message emphasizes that organizational failures rarely result from a lack of ideas. Instead, they stem from cultural, political, and psychological barriers that prevent those ideas from succeeding. He is available to provide expert commentary on leadership and organizational change, including how executives can sustain trust and momentum during crises, why workplace cultures often falter in execution, and how to foster environments where innovation thrives. He also addresses the evolving expectations of employees in the future of work, explains why the majority of brand and business transformations fail, and offers strategies to design change that lasts. CHAPTERS 00:00 Getting Into Change Management 07:26 What Kills Great Ideas? 14:05 Aligning Individual Self-Interests 17:25 Ad 17:56 The Reality of Reorganization 27:35 Unexpected Transformation 31:02 Looking for Change! 34:50 Ad 35:00 Team Capacity vs Company Demand 40:30 CTOs Have Power! 47:06 Organizational Cynicism WHERE TO FIND BUD • Website: https://nobl.io • LinkedIn: https://www.linkedin.com/in/budcaddell

We Sacrifice People for Performance. AI Is About to Make That Impossible ft. Margôt van Brakel

This episode challenges a core assumption most tech leaders still operate under: that intelligence is our primary advantage. As AI systems begin to outperform humans in reasoning and decision-making, this conversation reframes AI not as another step in the industrial revolution, but as the start of an intelligence revolution. For CTOs and business leaders, this shift forces a deeper question. If machines can think, what is left for humans to lead? You’ll learn why performance-driven organizations are hitting a ceiling and why continuing to optimize for efficiency alone will limit long-term value. The discussion explores a transition already underway, from purely economic thinking toward purpose, connection, and responsibility. It also highlights how board-level conversations are evolving, moving from short-term business cases to broader value-based decisions that shape the future of the organization and society. The episode also brings this down to action. It outlines how leaders and teams can respond today through experimentation, curiosity, and intentional time spent on change rather than just execution. You’ll walk away with a clearer perspective on how to position your organization in a world where AI handles more of the thinking, and where leadership is defined by the ability to rethink strategy, culture, and human contribution at a fundamental level. Key Takeaways • AI is replacing not just manual work but cognitive work, forcing leaders to redefine human value beyond intelligence • Performance-driven cultures are reaching their limits; future organizations must prioritize meaning, connection, and long-term value • Strategy must shift from pure business cases to value cases, balancing today’s results with tomorrow’s impact • Leaders should foster experimentation by allocating time for learning, not just execution, to unlock AI’s real potential • Organizations that combine human strengths with AI effectively will outpace slower, legacy-driven competitors • The most critical leadership skill ahead is not control, but curiosity, responsibility, and the ability to rethink assumptions ABOUT MARGÔT Margôt van Brakel is a keynote speaker, author, and advisor with more than 20 years of experience guiding organizations through complex change. She works with boards and executive teams on the human side of AI — exploring how organizations can use technology as a means, not an end, and find the right balance between people and machines. Her work focuses on what it means to keep human value at the center of organizational transformation. Because this is not the next wave in the industrial revolution — it is a new one. And that changes everything about the questions leaders need to ask. CHAPTERS 00:00 Margôt Journey 05:42 Treating People as Machines 12:38 AI's Societal Impact 12:06 Ad 20:32 What is Your Responsibility? 26:00 What is Homo Conexus? 39:01 Ad 38:12 The Ugly Phase of Transformation 42:25 A Hopeful Perspective! WHERE TO FIND MARGÔT • Website: https://margotvanbrakel.com • LinkedIn: https://www.linkedin.com/in/margotvanbrakel/ • Instagram: https://www.instagram.com/margotvanbrakel/