Dispatches from an Internet Pioneer

Deep Dive: Negotiation Styles

In this episode, we dive into the psychology and structure of negotiation based on the frameworks of Chester Karrass and Chris Voss. By exploring distinct negotiation styles and the role of silence, we reveal how awareness and adaptability can transform conflict into trust and effective leadership.

Deep Dive: The Power of Strategic Restraint in Leadership

This episode examines the transformative impact of strategic restraint, preference falsification, and calibrated silence in higher education leadership and large-scale institutional change. Drawing from economics, negotiation theory, and real-world IT leadership, we reveal how saying less—and listening more—can foster trust, collaboration, and lasting influence.

Deep Dive: The VMware Dilemma

What happens when the backbone of your IT infrastructure suddenly costs dramatically more? Broadcom’s overhaul of VMware pricing has left CIOs scrambling, caught between the risks of staying put and the costs of moving on. This episode unpacks the VMware dilemma: why the product is still indispensable for business continuity, why swapping it for another platform only trades one dependency for another, and why the real way out is a SaaS future.

Deep Dive: Hiring for the Long Game

Hiring IT staff in higher education is harder than ever, but not for the reasons most people think. In this episode, we unpack why chasing mid-career “plug-and-play” hires is a trap that drains budgets, creates salary compression, and fuels churn—and why the only sustainable strategy is to hire at the entry level, promote from within, and build real pipelines of talent. We walk through five rules for making better hires, explore the five core competencies that matter more than any technical skill, and share practical interview questions and development practices that help leaders cultivate teams that thrive, grow, and stay.

Deep Dive: Why ERP Implementations Fail

In this episode, Mark and Olivia dig into why ERP projects so often fail before they begin—and why surviving one can turn a good manager into a great leader. They break down the crucial first months, the systemic challenges, and the unexpected personal development baked into every step.

Shadow IT and the Illusion of Innovation

Is Shadow IT a sign of innovation or a symptom of institutional short-termism? This episode explores the hidden costs of side-door technology projects in higher education, drawing on three provocative essays about GenAI-fueled coding, technical debt, and the erosion of enterprise IT governance. Listeners will learn why sustainable transformation requires more than speed or tools; it demands discipline, strategic alignment, and the resolve to simplify before building.

Deep Dive: The Negotiation Escalation Ladder

This episode explores the subtle ways conversations shift from collaboration to confrontation, breaking down the five rungs of the negotiation escalation ladder. We discuss how to recognize each move — from quiet bargaining and extreme anchors to appeals to authority and personal attacks — and share practical strategies to stay grounded and protect relationships under pressure. You’ll learn how to respond with calm clarity instead of impulse, use tactical empathy to defuse tension, and preserve trust even when emotions run high. Whether you’re managing a tough deal or navigating delicate internal dynamics, this conversation offers a practical guide for leading with patience, awareness, and lasting credibility.

Deep Dive: Storm Scars and Bright Skies

In this episode, we explore how four major disruptions, the dot-com collapse, the Great Recession, the pandemic, and the unraveling of federal higher ed policy, have shaped a generation of CIOs in higher education. What begins as resilience can quietly become a mindset of perpetual caution, where innovation is seen as risky and vision gives way to survival. Drawing on lived experience, we unpack the subtle toll this takes on institutional imagination and offer practical ways IT leaders can balance stewardship with strategic boldness. It’s a conversation about weathering storms, without forgetting how to fly.

Deep Dive: Negotiation and CIO Credibility

In this episode, we explore why negotiation isn’t just a helpful skill for CIOs—it’s a defining one. Drawing on lessons from the dot-com crash, The New CIO Leader, and two decades of real-world leadership, we unpack how the best IT leaders use negotiation to build credibility, align expectations with resources, and earn the trust of their institutional partners. From the Credibility Cycle to the danger of becoming the “no police,” this conversation reframes negotiation as the core discipline that turns technologists into trusted enterprise leaders.

Deep Dive: Orchestrating AI-Infused Research

In this episode, we explore what it really takes to build an AI-infused university, going beyond buzzwords to the infrastructure, people, and processes that make it possible. Drawing on a three-tiered approach to research computing, from powerful desktop workstations to flexible cloud resources to the central high-performance computing cluster, we discuss how universities can balance investments for maximum impact. We look at why embedding faculty leadership into these decisions is critical, and how aligning compute, expertise, and workflow can turn AI ambitions into real research breakthroughs.

Deep Drive: ERP and Lifelong Leadership Lessons

In this episode, we unpack why ERP implementations, especially projects like Workday, are far more than system upgrades. They’re crucibles for leadership. Olivia and Mark share the skills every future leader builds during an ERP rollout, from narrative intelligence to governance fluency, and explains how these high-stress, high-stakes projects accelerate personal and professional growth. Whether you’re in IT, finance, HR, or academic leadership, this is a conversation about how to lead real change—and become the kind of leader institutions need next.

Deep Dive: What Makes Professors Great

In this episode, we explore what makes truly great professors unforgettable, not just for what they know, but for how they teach, mentor, and lead. From championing unconventional students to making complex ideas accessible, from modeling humility at the top to turning brilliance into a teachable process, they unpack the quiet, lasting impact of faculty who shape minds and institutions alike. It’s a conversation about presence, generosity, and the kind of leadership that begins in the classroom but reaches far beyond it.

Deep Dive: ERP Success Starts Outside IT

In this episode, we explore why ERP implementations in higher education so often struggle and what it really takes to make them succeed. Drawing on two decades of CIO experience and four major system rollouts, including a current 26-institution Workday deployment, we unpack the myth that ERP is a technology problem. It’s not. It’s a leadership challenge, a trust-building process, and a test of institutional clarity. From construction metaphors to boardroom crises, we trace how stakeholder-led change, not IT-driven execution, is the difference between systems that function and systems that last.

Deep Dive: Sweating the Details Together

In this episode, we unpack what it really means to “sweat the details together”—not as a micromanagement tactic, but as a leadership philosophy rooted in trust, clarity, and shared accountability. Drawing on lessons from Elon Musk, Robert Iger, and years of leading teams, we explore why structured team rhythm, strategic listening, and collaborative problem-solving are essential for real progress. We’ll walk through ten guiding principles that have shaped how I lead, build culture, and develop the next generation—not through performance theater, but through disciplined, mission-focused work.

Deep Dive: The Ideal CIO

In this episode, we explore what it truly means to be an ideal university CIO today — far beyond managing systems or fixing Wi-Fi. We discuss how the CIO has evolved into a strategic executive and cultural architect, responsible for aligning technology with mission, simplifying work, building trust, and guiding institutions through continual disruption. Drawing on real-world lessons and field-tested insights, we unpack what boards should look for, what candidates should hold firm to, and why this work demands clarity, courage, and deep alignment. Whether you’re a higher ed leader, an aspiring CIO, or someone fascinated by the intersection of technology and culture, this conversation offers a candid, inspiring guide to leadership that shapes the future.

Deep Dive: The Power of Silence in Negotiation

In this episode, we break down why leaders and negotiators often lose power the moment they start talking too much — and how real influence is built through silence, patience, and deep listening. Drawing on lessons from Chris Voss’s tactical empathy, Chester Karrass’s emphasis on patience as leverage, and vivid real-world examples from higher education and high-stakes negotiations, we reveal how over-talking leaks your strategy and hands control to your counterpart. You’ll learn to replace pitching with calibrated questions, transform silence into your sharpest tool, and build a culture where listening uncovers hidden truths that shift outcomes. If you’re talking, you’re losing — but when you listen, you win.

Deep Dive: Mandela's Legacy of Leadership

What does it take to leave a legacy that lasts? This episode draws on Nelson Mandela’s quiet refusal of conditional release in 1985 to explore seven essential lessons for leaders at the peak of their careers. From the power of principled restraint to the quiet strength of patience, clarity, and service, it offers a blueprint for finishing well—not by holding on to influence, but by investing in the people and convictions that will outlast you.

Deep Dive: The Hidden World of Shadow AI

This episode explores one of the most overlooked dynamics in today’s workplace: the widespread, hidden use of generative AI. As tools like ChatGPT and Copilot quietly reshape how work gets done, many employees are using them without disclosure, concerned about judgment, policy violations, or reputational harm. The result is a growing trust gap inside organizations, where the methods behind the work remain invisible and accountability becomes harder to enforce. The episode examines why this concealment is structural rather than personal, showing how vague policies, limited training, and cultural stigma are encouraging silence. It also outlines the risks, from compliance breakdowns to weakened team dynamics, and offers a clear challenge to leaders: shift the focus from managing tools to building a culture where transparency, trust, and responsible AI use are the norm.

Deep Dive: The Case for Paper and Pen

This episode explores the surprising power of deep listening and handwritten notes in a digital world. Olivia and Mark dig into research, real-world leadership lessons, and practical frameworks for organizing knowledge and attention. Discover why sometimes, slowing down beats speeding up.

Deep Dive: AI and Jobs—What Actually Changes

In this episode, we dive into the quiet revolution reshaping the modern workplace—not through mass layoffs, but through the erosion of routine, entry-level roles. AI isn’t just automating tasks; it’s redefining the very structure of knowledge work. We explore the Knowledge Worker Value Map, a powerful framework that categorizes roles into four quadrants—Executor, Integrator, Synthesizer, and Orchestrator—based on their adaptability and impact. You’ll learn why the future belongs to those who can synthesize, lead, and collaborate across domains, and why institutions must urgently rethink how they hire, train, and educate. Whether you're a professional navigating career shifts, a business leader planning for the future, or an educator shaping the next generation, this episode offers a clear-eyed look at how to stay relevant—and necessary—alongside AI.

Deep Dive: Seeing How College Pays Off

In an age when many are skeptical of the value of higher education, Georgia Degrees Pay offers a rare, data-driven approach to transparency. Operated by the Board of Regents of the University System of Georgia, the platform helps students and parents assess the true cost and impact of a college degree by providing clear insights into tuition, financial aid, debt, graduation rates, and real earnings of graduates over time. Unlike promotional materials that sell a dream, it delivers nuanced data—salary percentiles, scholarship retention, and institutional comparisons—so families can make informed, strategic decisions. By prioritizing facts over marketing, Georgia Degrees Pay empowers users to define the worth of a college education on their own terms.

Deep Dive: The GenAI Build-it Trap

In an era where AI makes custom coding easier than ever, universities must balance innovation with sustainability. This podcast explores the exhilarating appeal of coding—both by hand and with GenAI—while exposing the long-term complexities it introduces. From the legacy of fragile, homegrown systems to the strategic adoption of low-code solutions, we examine how institutions can harness AI without repeating past mistakes. Through a four-part discussion, we define where custom code truly belongs, how vendor-supported platforms enhance efficiency, and why leadership in the AI era is not about how fast we can build, but how clearly we can see. The institutions that thrive won’t be the ones that code the most, but the ones that apply thoughtful restraint—cutting through the Gordian Knot rather than tightening it.

Deep Dive: Edge, Leverage, and Trust

In this episode, we explore the Edge–Leverage–Trust model—a strategic framework that balances centralized efficiency with decentralized innovation in complex organizations. Drawing from experiences at Indiana University, Raytheon, and the University of Georgia, we examine how this approach enables research institutions to scale core IT services while empowering individual units to innovate. Ideal for leaders in higher education and research-driven enterprises seeking to align IT structures with institutional missions.

Deep Dive: Staying in the Room

In this Dispatch, we explore what negotiation reveals about leadership—especially within the complex, trust-dependent dynamics of higher education. Drawing from the careers of prominent CIOs and the insights of Chester Karrass and Chris Voss, we examine why extreme anchoring may win the moment but lose the room. Instead, we spotlight three durable strategies—clear concessions, early agenda-setting, and transparent openings—that foster influence over time. Whether you’re leading a systems overhaul or building cross-campus alignment, this episode invites you to negotiate with the kind of integrity that keeps you in the room.

Deep Dive: Cutting that Gordian Knot

In this episode, we explore what it really takes to modernize ERP systems in higher education. Drawing from the vivid metaphor of Gartner’s Andy Kyte—who once took the stage wielding a scimitar—we unpack why adopting platforms like Workday or Oracle Cloud won’t transform your institution unless you first confront the complexity you’ve inherited. From over-customized systems to data chaos and brittle workflows, this conversation cuts to the heart of ERP transformation: not technology, but work simplification. If you’re planning your next big implementation, this is the episode you need before making your next move.

Deep Dive: Being Cautious vs Driving Change

This episode dives into one of the most pressing dilemmas facing higher education technology leaders today: how to balance the drive for innovation with the need for operational resilience. It unpacks why colleges and universities so often default to caution—protecting legacy systems, processes, and risk-averse cultures—and explores the consequences of that mindset, from rising tuition and administrative bloat to eroding public trust. Through the lenses of the Gartner Hype Cycle and Christensen’s Innovator’s Dilemma, the episode examines why timing matters, why higher ed can’t afford to invest like a venture capital firm, and what gets lost when innovation is confined to pilot projects. Listeners will come away with a deeper understanding of the cultural and strategic forces at play—and practical insights for leading through the tension rather than avoiding it.

Deep Dive: Who’s Really Winning the Everyday AI race in Higher Ed?

Who’s really winning the GenAI race in higher education—and why does it matter? In this episode, we explore how Google, OpenAI, and Microsoft are shaping the future of AI on campus. From powerful chatbots to personalized learning tools, you’ll hear a breakdown of what each platform offers, where they fall short, and how they stack up in terms of usability, cost, and institutional readiness. Whether you’re an educator, IT leader, or curious student, this episode offers clear insights into the tools that are transforming how we teach, learn, and work. Don’t miss this strategic look at the evolving AI landscape in higher ed.

Deep Dive: The AI-Infused University

Universities globally are adapting to an AI-infused future. Navigating the AI revolution in higher education requires actionable strategies to make smart AI investments, avoid common pitfalls, and achieve real impact. This podcast discusses how AI enhances teaching, research, and administration, explores strategic investments for maximizing productivity, and addresses risks like cultural resistance and cybersecurity.

Deep Dive: Leading Through Higher Ed’s Fourth Crisis

In this episode of Deep Dive, we explore what it takes to lead higher education IT teams through profound uncertainty. Drawing on lessons from four major crises—the dot-com crash, the Great Recession, the COVID-19 pandemic, and today’s unfolding policy-driven disruption—this episode offers a leadership playbook built on clarity, emotional endurance, and calm. Whether you’re a CIO, a mid-career leader, or someone navigating change on your campus, this conversation unpacks the quiet skills that matter most when the road ahead disappears.

Deep Dive: GenAI, Copyright, and Global Competition

In this week’s dispatch, we unravel the complex legal challenges surrounding generative AI—challenges that could shape not just the future of technology, but America’s role in leading it. From The New York Times v. OpenAI to Getty Images v. Stability AI, the courtroom battles are heating up, raising urgent questions about what counts as fair use in a GenAI-driven world. We explore what’s at stake for U.S. innovation, contrasting America’s legal gridlock with China’s more permissive approach to copyright and data use. As China accelerates GenAI development with fewer restrictions, we examine whether the U.S. can strike the right balance—protecting creators without stifling the very innovation that built Silicon Valley.

Deep Dive: Rethinking Scale in the Era of Vendor Lock-In

This episode explores why the long-standing strategy of scaling through vendor standardization is now putting higher ed IT at risk. As costs rise and vendor flexibility shrinks, institutions need a new playbook—one built on diversification and leverage. Drawing from real-world examples, including a survey tool negotiation turned case study, we break down how CIOs can regain control by adopting a “Lexus and Toyota” model across their IT portfolios.

Deep Drive: How Tech Disrupted Trust

In this episode, we explore how the Internet, smartphones, and artificial intelligence have fundamentally reshaped the way we connect—not just to information, but to one another. Drawing from decades of experience as a higher ed CIO and trained sociologist, I walk through the three major tech shifts of our time—1993, 2007, and 2022—and examine how each one chipped away at the traditional institutions that once structured our social and civic lives. What began as a promise of empowerment has left us tethered to algorithm-driven platforms, disconnected from shared norms, and increasingly polarized. From the collapse of gatekeeping to the rise of brittle, many-to-many networks, this episode reflects on what we’ve lost, what we’ve learned, and what it might take to rebuild trust in the digital age.

Deep Dive: The Quiet Work of Great Leaders

In today’s episode, we’re talking about mentorship—but not the kind you find in structured programs or formal pairings. This is about the kind of mentorship that happens in the trenches—when you’re working for someone who believes in you, challenges you, and shapes you through how they lead every day. If you’re early in your career, this episode will give you a sense of what to look for in a great boss. If you’re further along, it’s a reminder of the kind of leader we should all strive to be.

Deep Dive: Understanding and Countering Extreme Anchors

Extreme anchoring isn’t just a negotiation tactic—it’s a strategy for shifting the entire debate in your favor. In this episode, we explore how Donald Trump uses extreme anchoring to move the Overton Window, forcing opponents to react while keeping the final outcome closer to his political agenda. Drawing from The Art of the Deal, we break down real-world examples from business, reality TV, and politics, and discuss how other leaders—like Reagan and FDR—have successfully redefined mainstream discourse. Plus, we dive into an FBI negotiator's playbook to explore how to counter extreme anchors effectively in leadership, business, and everyday conversations. Listen in to learn how to recognize and respond when someone shifts the playing field on you.

Deep Dive: GenAI and the Economic Revolution of Work

This episode examines how GenAI could drive economic transformation by radically simplifying workflows, contrasted with the Internet's success in 1993 and the iPhone's limited productivity impact in 2007. Learn practical work simplification principles inspired by Toyota and their application in sectors like healthcare and cybersecurity. We also address the cultural hurdles and structural resistance that slow GenAI adoption, featuring insights from a CIO's leadership journey.

Deep Drive: The Hidden Memory of Generative AI

Generative AI tools like ChatGPT, Microsoft Copilot, and Google Gemini retain more user data than most people realize, raising serious ethical, legal, and privacy concerns. In this episode, Olivia and Mark explore real-world cases, including sensitive data retention in a government agency, and the growing challenges of AI-driven profiling and data transparency. They discuss how AI systems silently build user “digital twins,” why privacy compliance is struggling to keep up, and what needs to change. If you think AI forgets, think again—tune in for a deep dive into AI memory, regulation gaps, and the urgent need for user control.

Deep Dive: The Case for Low-Code Everyday AI in Higher Ed

This episode examines why low-code everyday AI is the smarter, more sustainable choice for higher education—and why the old “build-it” mentality no longer works. IT organizations are under pressure to adopt everyday AI, but custom-built solutions are expensive, insecure, and impossible to maintain at scale. We break down the real costs of DIY AI, the security risks of homegrown models, and why higher ed IT has already moved away from custom development in other areas. Tune in to explore a practical everyday AI adoption strategy that balances innovation, cost containment, and long-term viability.

Deep Dive: AI's Growing Role in Higher Education

This episode examines the real role of AI in higher education—what’s useful, what’s overhyped, and where universities should actually invest. With AI adoption accelerating, institutions face a critical choice: embrace low-cost everyday AI for efficiency or pursue high-stakes, game-changing AI with long-term impact. We break down the differences, explore real-world use cases, and discuss smart AI strategies that balance innovation with financial sustainability. Tune in to cut through the hype and discover how AI can truly transform higher ed—without unnecessary risks.