Podcast
Dispatches from an Internet Pioneer Podcast
Hosted by Timothy Chester · EN
Exploring the intersection of technology, leadership, and society—through the lens of an Internet pioneer in higher education. Insightful discussions on AI, digital transformation, and the future of work.
dispatchesinternetpioneer.substack.com
dispatchesinternetpioneer.substack.com
11episodes
Episodes
Newest firstAll episodes
Deep Dive: The Rise and Risk of Remote Work
Feb 500:12:09Tap to summarizeThe "Laptop Test" identifies a critical vulnerability: roles performed entirely via screens are most susceptible to systematic automation. As Generative AI commoditizes pure cognitive labor, the removal of physical presence strips away the institutional connective tissue, social capital, informal negotiation, and alignment labor that serves as a human moat against displacement. This shift risks turning remote work into a career dead end by hollowing out the apprenticeship rungs of the professional ladder. Survival in this landscape requires a transition from digital execution to institutional orchestration, favoring those who move beyond performative presence toward integrated, high-fidelity leadership.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/remote-work-is-fast-becoming-deadEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: Leading Without Surprise
Jan 2900:11:35Tap to summarizeThis episode explores how CIOs can lead meaningful change without surprising their institutions. We examine the difference between decision rights and influence rights, the real source of pushback during policy rollouts, and why predictable structures like the Two Readings Method help stakeholders engage more thoughtfully. We look at the psychology behind second exposure, where confusion turns into clarity, and highlight how an accusation audit can lower defensiveness by naming concerns upfront. The episode offers a practical roadmap for CIOs who want to build trust, reduce conflict, and lead with credibility in complex institutional environments.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/the-rhythm-of-leading-without-surpriseEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: When Hype Collides with Reality
Jan 2200:12:53Tap to summarizeWe explore how the real Internet emerged not from the frenzy of the dot-com boom but from the discipline that followed its collapse. We walk through five themes that still shape every major technology wave: hype’s habit of outrunning capacity, the way scarcity builds what abundance cannot, the shift from charismatic vision to rational judgment, the unexpected transformations that only austerity revealed, and the leadership lesson that discipline always outlasts innovation theater. It is a conversation about how institutions learn, how they fail, and how the patterns forged in the early 2000s offer a clear warning for an AI era powered by confidence and debt.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/the-real-internet-emerged-after-theEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: Queue Time, Flow Management, and the True Path to Productivity
Jan 1500:12:39Tap to summarizeThis episode examines a fundamental truth for all service leaders: excessive queue time, rather than a lack of resources, is the primary destroyer of customer trust. Drawing on process analysis, we argue that true productivity requires radical work simplification and structural discipline. We dissect the hidden costs of disorganized flow, the corruption of political queue jumping, and the failure of the first-in, first-out (FIFO) principle. Learn why leaders must shift focus to metrics like Queue Aging and Work in Progress, and how applying Lean Six Sigma can create leaner, more accountable service processes across a university.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/the-queue-time-is-the-killerEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: When Silence Signals Trouble
Jan 800:12:39Tap to summarizeHow do quiet meetings become the downfall of massive technology projects? We explore the hidden dangers of polite agreement in ERP design, unraveling how small missteps ripple into institutional failure. This episode unpacks the true meaning of alignment, the cascade of consequences, and the leadership required to challenge silence before it’s too late.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/silence-is-the-killer-the-cascadeEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: Who Should the CIO Report To?
Dec 1100:12:23Tap to summarizeThis episode explores how the reporting line of a Chief Information Officer (CIO) in higher education influences their authority, responsibilities, and effectiveness. We break down the ‘ideal type’ CIO using a sociological lens, dig into why university leadership chooses certain reporting structures, and compare real-world differences between CIO roles reporting to presidents, provosts, and CFOs.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/who-the-cio-works-for-matters-inEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: The Illusion of Innovation
Dec 400:16:49Tap to summarizeIs 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.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/shadow-it-isnt-innovation-its-poorEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: The Power of Strategic Restraint
Nov 2000:12:37Tap to summarizeThis 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.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/private-truths-public-leadershipEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: Why ERP Implementations Fail
Nov 1300:15:21Tap to summarizeIn this episode, we unpack why ERP projects so often go sideways, not because of bad technology, but because institutions skip the hard, early work of process discovery and redesign. We trace the evolution of ERP systems across four generations, explain why modern cloud platforms like Workday only deliver value if paired with institutional clarity, and explore how executive distance and surface-level planning quietly sabotage even the best-intentioned projects. If you’ve ever wondered why go-live feels like chaos, this conversation explains why and how to avoid it.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/the-first-six-months-decide-everythingEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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Deep Dive: Negotiation Styles
Nov 600:13:27Tap to summarizeIn this episode, we explore the art and science of negotiation through the frameworks of Chester Karrass and Chris Voss, examining how structure, empathy, and silence shape outcomes. The discussion unpacks the three core engagement styles: Assertive, Accommodator, and Analyst, and how recognizing each can transform conflict into collaboration. By learning to balance logic with emotion and to use silence as a strategic tool, leaders can build credibility, deepen trust, and turn negotiation into a practice of awareness and respect.Based on Substack article:https://dispatchesinternetpioneer.substack.com/p/know-your-negotiation-styleEnergetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit dispatchesinternetpioneer.substack.com
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