Coffee With Digital Trailblazers

StarCIO Digital Trailblazer Community
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Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffee Digital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving transformations in their organizations and life. About the Coffee with Digital Trailblazers Every week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate. Topics that we cover: digital transformation, AI. genAI, AI agents, agile, DevOps, data science, data governance, IT leadership, CIO, CDO, CMO, CHRO

  1. 1d ago

    Vibe, Buy, or Automate? Deciding How to Build AI Agents

    We discuss a framework for organizations deciding to buy, build, or vibe AI agents. Key factors included data availability, risk levels, and governance to prevent unregulated AI use. The panel emphasized the distinction between automations and true AI agents, suggesting clear guidelines for development. Chapters (00:00:00) - Technical Start & Episode Introduction(00:01:07) - Research Background: AI Agent Sprawl(00:04:40) - Decision Framework: Deterministic vs Judgment-Driven Agents(00:07:26) - Greg Hack Introduces Risk and Shadow AI Concerns(00:10:43) - Tokenization, Accountability and Value as Control Levers(00:14:00) - Joe's Three Questions: Clarity, Stability, Ownership(00:15:42) - Joanne's Framework: Known Paths vs Judgment and Exceptions(00:19:10) - Low-Level Agent Examples and Personal Use Cases(00:20:42) - Martin: Structured AI vs Shadow AI Risk(00:22:49) - Dangerous Gray Areas in AI Data Governance(00:24:49) - John's Work: AI Coaching and Hybrid Agent Futures(00:27:15) - Upcoming Coffee Hour Topics and Schedule(00:28:51) - Greg's Four Questions: Buy, Vibe, Build, Hybrid(00:34:12) - When Build Makes Sense: Process Complexity and Choreography(00:38:17) - John on Spec-Driven Development vs Vibe Coding(00:43:33) - Department of Know: Case-by-Case Governance Decisions(00:48:37) - Liz on Shadow AI Value and Governance Allocation(00:51:19) - Martin on Historical Chaos (VBA) and AP Automation Example(00:53:58) - Controlling Chaos: Guardrails, Strategy, and Reuse(00:57:02) - Closing: Who Owns AI Agents & Wrap-Up

    Vibe, Buy, or Automate? Deciding How to Build AI Agents

  2. 5d ago

    Getting Hired in the AI Era: Stand Out, Signal Judgment, Land the Role

    Isaac led a discussion focusing on strategies for job seekers in the AI era, highlighting the importance of standing out, signaling judgment, and landing roles. Panelists emphasized showcasing AI expertise, adaptability for C-level positions, and the significance of cultural fit. Insights included the value of self-assessment and problem-solving skills. Chapters (00:00:02) - Welcome and Episode Overview(00:02:38) - Research Data: Hiring Trends and Statistics(00:07:03) - Standing Out: Portfolios and Demonstrated Skills(00:09:56) - Standing Out: SOC and Security Examples(00:12:54) - Standing Out for C-Level: Adaptability and Judgment(00:18:44) - Executive Recruiter Perspective on Standing Out(00:22:39) - How Recruiters Screen Hundreds of Candidates(00:27:00) - Communication, Homework, and Personal Branding(00:30:30) - Martin and Liz on Fit and Skills Alignment(00:34:26) - October Programming Preview(00:36:57) - Signaling Judgment: AI Governance and Strategic Thinking(00:41:11) - Signaling Judgment: Value Creation Examples(00:44:19) - Signaling Judgment: Case Studies and Relevance(00:48:25) - Landing the Role: Handling Rejection and Follow-up(00:52:20) - Landing the Role: Being Memorable in Interviews(00:55:31) - Landing the Role: Culture Fit and Final Thoughts(01:01:42) - Closing Remarks and Upcoming Topics

    Getting Hired in the AI Era: Stand Out, Signal Judgment, Land the Role

  3. Sep 21

    Tech Budget 2027: What AI Bets to Fund + IT/Security to Protect

    We focused on technology budget planning for 2027, particularly AI funding strategies. Host Isaac Sacolick led a discussion with panelists on prioritizing AI initiatives, emphasizing strategic clarity and measurable outcomes, while addressing budget protection and identifying areas for potential cuts. Key frameworks were also presented. Chapters (00:00:00) - Introduction and Episode Overview(00:00:40) - Setting the Scene: 2027 Tech Budget Challenges(00:01:37) - Research: Signs of an AI Bubble and Data Points(00:04:22) - Scenario Setup: 200 Agents by End of 2027(00:06:18) - John's Pitch: Security and Governance Funding(00:08:32) - Liz's Pitch: Business Problem Focus and Frontline Use Case(00:11:06) - Joanne's Pitch: Agentic Control and Execution Layer(00:14:02) - Debate on Orchestration, Control Planes, and Agent Collisions(00:18:58) - Strategy Before Tools: Vision Statements and Outcomes(00:21:49) - Derek's Cause: Prostate Health Awareness Ride(00:23:10) - Derek's Pitch: AI Agent Resilience and Governance(00:25:40) - Joe's Pitch: Extraordinary Governance and Metrics(00:27:38) - Isaac's Alternative Scenario: Training and Change Management(00:28:44) - Show Announcements and Upcoming Events(00:30:19) - New Scenario: Recession Planning - Protect vs Cut(00:32:47) - Joanne's Protect/Cut: Control Plane and Token Spend(00:34:25) - Derek's Protect/Cut: Identity Security and App Consolidation(00:37:28) - Joe's Protect/Cut: Education Over External Consulting(00:39:34) - Liz's Protect/Cut: Token Optimization and Contextual Training(00:40:54) - Joanne on Business Process Re-engineering(00:43:31) - Isaac's Protect/Cut: Data Governance, RPA, Spreadsheets, Meetings(00:45:30) - Final Round: Setting Priorities as CIO/CAIO(00:46:26) - Derek's Framework: Value, Risk, Resilience, Readiness(00:48:19) - Liz on Strategy-Driven Prioritization(00:51:01) - Joanne on Differentiable Value and Institutional Knowledge(00:53:52) - Isaac on AI in Customer Experience and Force Multipliers(00:55:02) - Joe's Framework: Outcomes, Risk, and Probability of Success(00:58:18) - Joanne's Closing Point: Irrevocability as a Priority Filter(00:59:30) - Wrap-Up and Upcoming Schedule

    Tech Budget 2027: What AI Bets to Fund + IT/Security to Protect

  4. Sep 14

    The Hidden Cost of Confident AI: Semantics, Guardrails, and the Context Layer

    The discussion led by Isaac Sacolick focused on AI challenges, particularly the "hallucination tax," emphasized by Felix Van de Maele, CEO of Collibra. Contributors highlighted the importance of governance, context engineering, and policy to mitigate AI failures and improve trust. Future topics included AI existential risks and economics. Chapters (00:00:00) - Introduction and September 11th reflection(00:01:59) - Research data on agentic AI failures and governance gaps(00:04:42) - Introducing Felix Van de Maele and hidden AI costs topic(00:05:42) - Defining the hallucination tax(00:08:28) - Trust, employee analogy, and human oversight(00:11:06) - Measuring the hallucination tax and feedback loops(00:13:08) - Liz's question on managing context and reducing token usage(00:14:33) - Building and maintaining context as a living artifact(00:17:50) - Derek on AI debt and confidence risks(00:20:16) - AI policies, guardian agents, and enforcement(00:22:19) - Deep dive into the context layer and its fragmentation(00:26:19) - Joe on communicating AI concepts and instilling doubt in agents(00:31:51) - Sponsor break: Collibra as the enterprise AI control plane(00:32:40) - Defining and evolving the semantic layer(00:36:04) - Martin's industrial revolution analogy and guide rails(00:39:23) - Joanne's agentic A-list framework for governance(00:44:54) - Implementing AI governance in practice(00:49:10) - Clarifying Collibra's AI governance offering(00:52:35) - Trust, provenance, and lineage as governance foundation(00:55:00) - Closing thoughts: business case, layered governance, and closing remarks

    The Hidden Cost of Confident AI: Semantics, Guardrails, and the Context Layer

  5. Aug 31

    SaaS, Cloud, and AI Contracts: Where Technology Leaders Lose Leverage

    The 186th episode of Coffee with Digital Trailblazers focused on negotiation tactics for SaaS contracts. Key topics included competitive bidding, avoiding auto-renewals, and ensuring data ownership. Martin Davis presented a checklist of 88 clauses, while participants emphasized the importance of thorough reviews and understanding data rights, especially for AI models. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:01:36) - Why Your SaaS Contracts Are Unreasonably Expensive(00:03:07) - Five Things to Look Out For In Your Cloud Contracts(00:05:57) - How To Negotiate Contract Terms With Software & SaaS(00:10:28) - CIO Network: How Much Time Should a CIO Spend on(00:11:09) - Choosing the right SaaS vendor(00:14:46) - 3 Tips for SaaS and AI Contract Terms(00:18:40) - CIO Network: Data and AI Terms(00:22:44) - 3 Rules for Software Contract Negotiations(00:25:55) - 3 Rules for Negotiating Contracts(00:29:30) - Microsoft Software Switching Costs(00:34:48) - Coffee With Digital Trailblazers(00:36:40) - No Auto-Renewing IT Contracts(00:41:47) - Data and AI(00:44:12) - Cloud Security: The First 2 Things(00:46:41) - SaaS and the use of data(00:48:33) - PPMO and Vendor Management(00:50:13) - What Do You Look For In A Cybersecurity Vendor? ((00:53:54) - SLAs and Performance Based Payments(00:56:12) - WSJD Live: Understanding Your AI Omissions(00:58:49) - What's the SaaS Exit?(01:00:16) - Coffee With Digital Trailblazers

    SaaS, Cloud, and AI Contracts: Where Technology Leaders Lose Leverage

  6. Aug 24

    Shadow AI at Work: Real Risks, Practical Guardrails, Hidden Innovation

    The real risks and practical guardrails around shadow AI, which goes beyond traditional shadow IT with new risks including data leakage, agentic AI poor decisions, and potential legal compliance issues. Chapters (00:00:02) - Coffee With Digital Trailblazers(00:01:09) - CIO Chat(00:01:51) - Shadow AI: How to Govern It(00:06:20) - CIO Network: Shadow IT and Shadow AI(00:09:30) - CIO Network: The Shadow AI Threat(00:13:10) - What's The Dark Side of Shadow AI?(00:15:36) - The Problem of Generating Content(00:16:48) - The Rise of AI's Rogue Users(00:18:10) - On the Board's Perspective on AI(00:21:24) - GM: What Should Companies Do About Shadow AI?(00:27:50) - Is AI a Threat to Human Life?(00:29:47) - The IT culture of swarm AI(00:31:01) - How to Educate the IT Team about AI(00:33:06) - Are We Ready for Shadow IT?(00:36:06) - Coffee With Digital Trailblazers(00:38:06) - John and Joanne on Shadows in AI(00:42:11) - Is AI Threats Affecting Your Business?(00:45:13) - CISO Video: From Implementation to Threat Intelligence Monitoring(00:46:39) - Pick A Scenario(00:50:54) - The Role of MCP in Threat Intelligence(00:52:04) - The Salesforce vs. General Counsel(00:55:18) - The IT Turnaround: Speed Over Safety(00:58:13) - John Hadley on AI and Governance(00:59:31) - AI Governance

    Shadow AI at Work: Real Risks, Practical Guardrails, Hidden Innovation

  7. Aug 17

    Beyond Legacy Processes: Engineering the High-Velocity Enterprise

    The session sponsored by Camunda, featuring CTO Daniel Meyer, focused on transforming legacy business processes for high-velocity enterprises in the AI era. Meyer highlighted the advantages of orchestrating workflows and selectively integrating AI, with examples of significant efficiency gains. A panel discussed trust in AI, phased adoption, and the evolving landscape of enterprise governance and collaboration. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:01:15) - Beyond Legacy Processes: Automation & Processes Engineering(00:03:25) - A New Dimension in Business: AI Reengineering(00:04:48) - Will Businesses Replace Their Processes with AI?(00:06:10) - How to Orchestrate your Business Processes with AI(00:08:04) - REengineering for Financial Services: What We Need to Do(00:14:20) - Agile Process Reengineering and Agent Orchestration(00:19:25) - Machine Learning: Trust and Choreography(00:25:34) - How to Infuse AI into Your Processes(00:27:20) - Coffee With Digital Trailblazers(00:28:13) - Building Trust in the Age of AI(00:30:33) - Immersive Processes for Compliance and AI(00:33:53) - In the Age of AI: Decisions and Ownership(00:36:50) - AI and the Quality of Output(00:38:50) - Guardrails and Boundaries in Agentic AI(00:41:43) - Insurance: Guardrails and Agents(00:44:26) - Beyond the Hype: Process Automation(00:45:00) - What Does an Orchestrated Enterprise Look Like in 3 years?(00:52:13) - What the Orchestrated Enterprise Looks Like in 3 years(00:58:07) - Beyond the Organization: The Forward-Deployed Engineer(01:00:01) - Process Reengineering

    Beyond Legacy Processes: Engineering the High-Velocity Enterprise

  8. Aug 11

    Networking in the AI Era: A Guide for Digital Transformation Leaders

    An expert advisory panel discussed networking in the AI era, emphasized the importance of authenticity, curiosity, and relationship-building. Panelists explored strategies for meaningful connections at events and highlighted how AI has transformed networking, necessitating thoughtful preparation. In-person interactions remain essential for fostering lasting relationships beyond mere transactions. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:02:39) - How to Build a Deep Network in the AI Era(00:06:16) - The Secret to Networking in the AI Era(00:10:34) - How to Get Invitations to Spark(00:14:30) - Super Networkers(00:21:14) - CEM Business Network: Relationships(00:23:19) - Your SuperNetworking Power(00:24:14) - How to Network (Sales and Network)(00:25:52) - What's Your Super Networking Superpower?(00:26:56) - Network building at a conference or a dinner(00:28:16) - Martin on Connecting With People(00:33:17) - Coffee With Digital Trailblazers(00:34:02) - Michael Yates on Connecting With Others(00:35:21) - How To Network ((00:40:52) - How AI Is Changing Networking(00:46:50) - How to Network in AI(00:54:48) - Don't Use AI for Your Networking(00:57:00) - Last Word on AI and CIO Networking(01:00:17) - Coffee With Digital Trailblazers

    Networking in the AI Era: A Guide for Digital Transformation Leaders
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About

Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffee Digital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving transformations in their organizations and life. About the Coffee with Digital Trailblazers Every week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate. Topics that we cover: digital transformation, AI. genAI, AI agents, agile, DevOps, data science, data governance, IT leadership, CIO, CDO, CMO, CHRO

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