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Episodes (66)

Timothy Chester reflects on his experiences managing vendor licensing challenges, comparing Oracle's past strategies with today's issues from Broadcom and VMware. He explores how higher education institutions can learn from history to better handle vendor relationships and costs.

Timothy Chester shares a personal story from launching Texas A&M's Doha campus, emphasizing the importance of hiring for drive and potential over just skills. He discusses how investing in people with the right competencies can build stronger teams and better talent pipelines.

Timothy Chester shares insights from his 12 years teaching Business Process Management at the University of Georgia. This episode explores the importance of BPMN skills, the pitfalls of rushing ERP implementations, and why disciplined process improvement is crucial for project success.

Timothy Chester explores the realities of shadow IT through a recent CIO interview experience. This episode delves into why shadow IT forms, its persistence, and what it reveals about executive leadership and organizational priorities.

Timothy Chester shares insights from over two decades of executive leadership on maintaining collaborative, win-win negotiations. He explores how baseline relationships can escalate into tension and offers strategies inspired by Chester Karrass and Chris Voss to keep negotiations grounded and productive.

Timothy Chester shares a pivotal experience from his journey to becoming CIO at Pepperdine, revealing how understanding the human and cultural challenges behind technical projects can transform leadership. This episode explores how navigating ambiguity and building trust during ERP implementations can advance careers and develop impactful leaders.

Timothy Chester shares a compelling story about a hospital's electronic health record system failure and the crucial role of leadership in technology projects. Discover why stakeholder engagement and leadership structure matter more than technology in ERP implementations.

Timothy Chester explores C.S. Lewis's profound essay "A Slip of the Tongue," reflecting on the tension between spiritual minimalism and true discipleship. This episode invites listeners to consider their own negotiations with faith and the cost of genuine surrender.

Timothy Chester delves into C.S. Lewis's profound essay "The Weight of Glory," unpacking its themes of desire, discipleship, and eternal destiny. This episode invites listeners to reflect on longing, purpose, and what it means to be truly known by God.

Timothy Chester shares insights on the importance of regular team meetings for alignment, problem-solving, and trust-building. Drawing from personal experience and leadership examples like Elon Musk and Bob Iger, this episode explores the principles behind effective team rhythms.

Timothy Chester explores C.S. Lewis's essay "Learning in Wartime," reflecting on the significance of study and life during times of conflict. This episode delves into how Lewis encourages us to find eternal meaning beyond fear and practical duties, offering insights relevant for today's challenges.

Timothy Chester reflects on meaningful conversations with two CIOs at different career stages, sharing insights on trust, leadership, and the role of a CIO. He honors the guidance of his mentors Nancy Magnusson and Jere Morehead, exploring how stewardship shapes effective CIO leadership.

Explore the humble legal pad: its origins, unique features, and why it remains a staple for professionals. From history to practical tips, this episode uncovers the enduring charm of this classic tool.

Explore the Edge-Leverage-Trust framework and how businesses can use edge technology for competitive advantage. Timothy Chester draws on his experience leading digital transformation and building trust in complex organizations to illuminate key benefits and challenges of edge computing. This episode unpacks how strategic trust and innovation at the edge are shaping the IT landscape.

Explore the overlooked art of listening in negotiation. Discover how active listening builds trust, uncovers hidden interests, and leads to better outcomes. Timothy Chester shares real-world insights on listening techniques that transform the negotiation table.

Explore the pivotal themes of salvation, choice, and reality in Chapters 10 and 11 of 'The Great Divorce.' Timothy Chester breaks down how these chapters set the stage for deeper philosophical questions, using memorable characters to illustrate spiritual truths.

Choosing Heaven

This episode delves into Chapter 9 of 'The Great Divorce,' focusing on the allegorical struggle between pride and humility in the pursuit of salvation. Through the story of the Ghost and his former wife, we explore the challenges of letting go and the transformative power of forgiveness.

Explore how companies exaggerate their use of AI, the reasons behind the hype, and the consequences of misrepresentation. Discover why transparency about AI adoption matters more than ever in today's tech-driven world.

Explore the allegorical world of C.S. Lewis’s The Great Divorce as we examine pride, self-deception, and the spiritual choices that define us. Through vivid characters and philosophical dialogue, this episode unpacks the struggle between embracing truth and clinging to illusion.

Exploring C.S. Lewis's allegorical journey through heaven and hell, this episode dives into themes of guilt, pride, and the challenge of accepting forgiveness. Through vivid character encounters, we unpack how earthly attachments can hinder spiritual growth and what it takes to embrace true grace.

This episode explores C.S. Lewis's depiction of heaven and hell in The Great Divorce, focusing on the struggles of pride and earthly attachment in Chapters 3 and 4. Through vivid character studies, we discuss the barriers to spiritual growth and the choices that shape our destinies.

Explore the opening chapters of C.S. Lewis’s 'The Great Divorce,' as the podcast delves into the allegorical journey from a dreary, gray purgatory to the vibrant edge of heaven. Discover the spiritual and philosophical questions raised by the bus ride and the choices faced by its passengers.

Explore how AI is reshaping the job market, from automation and displacement to new career opportunities. Hosts discuss historical context, ethical questions, and real-world examples that illuminate the complex relationship between AI and employment.

Explore how higher education shapes earning potential in Georgia. We examine why investing in a degree matters, compare career outcomes by field, and highlight real-world impacts for Georgians. Discover what makes a degree valuable in the Peach State.

This episode explores the pitfalls and risks of developing custom AI code, questioning whether bespoke solutions are worth the trouble. The hosts discuss the hidden challenges, security concerns, and the case for using established AI frameworks.

Explore the significance of mindfulness in personal and professional settings. Discover how 'staying in the room' can enhance leadership, communication, and personal growth. Join Timothy Chester as he shares insights and experiences on being present.

Explore the delicate balance between caution and innovation, where stability meets creativity. Join Timothy Chester as he navigates the risks and rewards of both approaches, sharing insights from his extensive experience in IT leadership.