Coffee With Digital Trailblazers

StarCIO Digital Trailblazer Community

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. 6d ago

    Finishing Strong: How Digital Leaders Close Out the Year

    The 193rd episode of "Coffee with Digital Trailblazers" focused on strategies for digital leaders to successfully conclude 2026 and prepare for 2027. Experts emphasized the importance of vision, security measures, and team morale. Key recommendations included governance processes, escalation procedures, and recognizing team achievements to maintain enthusiasm and prevent burnout. Chapters (00:00:00) - Welcome and 5th Anniversary Celebration(00:01:24) - Setting Up Today's Topic: Finishing the Year Strong(00:02:04) - AI Value and Risk Research Data(00:04:29) - Ransomware Trends and Q4 Vulnerability(00:06:33) - Introducing Guests and Framing the Vision Question(00:07:53) - John's Advice: Reflection, Change Management, and Focus(00:10:25) - Derek: Looking Ahead, Not Just Wrapping Up(00:12:48) - Joe's BT Philosophy and Town Hall Approach(00:15:39) - Celebrating Successes to Offset Misses(00:17:27) - Heather: Consistency Over Year-End Specialness(00:19:35) - Meticulous Notes and Data for Year-End Narrative(00:20:35) - Joanne's Five Lessons for Finishing Strong(00:24:18) - Liz on Governance, ROI, and Culture(00:27:29) - Break and Announcements: Anniversary, Upcoming Topics, Webinar(00:30:20) - Avoiding a Q4 Security Crisis with Derek(00:35:59) - Joe's RCAT Rule: Remain Calm at All Times(00:38:53) - Heather and Joanne on Team Readiness and AI Agent Risk(00:42:34) - Handling Leadership Panic and Uncertainty(00:47:39) - Dealing with the Team Downer(00:51:27) - Winning as a Team: Recognize, Recover, Reset(00:52:42) - Personal Reflection and Leadership Self-Care(00:55:26) - Joe's Five Tips for Team Recognition(00:57:14) - Liz's Closing Thought: Celebrating Customer Value(00:58:29) - Closing Remarks and Upcoming Events

    Finishing Strong: How Digital Leaders Close Out the Year

  2. Oct 19

    AI Infrastructure Debt: Strategies for Capacity, Resiliency, and Modernization

    The episode on AI infrastructure debt highlights that weak data foundations limit AI potential, with organizations misidentifying performance challenges as only GPU issues. Experts stress the necessity of a hybrid cloud approach, emphasizing the importance of resiliency, human accountability, and modernization as a strategy for business acceleration amidst rapid data growth. Chapters (00:00:00) - Introduction and AI Infrastructure Debt Stats(00:03:01) - Sponsor Thanks: Hitachi Vantara(00:04:07) - Capacity Mistakes in AI Infrastructure(00:06:48) - Drivers of Capacity Growth and Technical Debt(00:11:14) - Panel: Capacity Lag and Growth Curve Discussion(00:13:17) - Agent Scaling and Data Movement Strategies(00:15:21) - Infrastructure Gaps and Cyber Resilience Risks(00:16:51) - Business Value vs Capacity Planning Pitfalls(00:18:54) - Workload-Based Capacity and Predictability(00:22:01) - Hardware Scarcity and Capacity Planning Horizon(00:26:27) - Governance, Data Sovereignty, and Data Quality(00:31:03) - Break and Sponsor Message / Houston Roundtable Invite(00:32:13) - Closing Capacity Thoughts and Transition to Resilience(00:33:37) - Cyber Resilience in AI Infrastructure(00:36:19) - Legacy Systems and AI Resilience Risks(00:38:22) - Monitoring, Predictability, and Response Automation(00:41:19) - AI Accountability, Human Oversight, and Risk of Harm(00:47:02) - Kill Switches and Extending Cyber Resilience(00:48:02) - Cloud vs On-Prem: Hybrid Infrastructure Decisions(00:52:17) - Building the Business Case for Modernization(00:58:52) - Closing Remarks and Sponsor Thanks

    AI Infrastructure Debt: Strategies for Capacity, Resiliency, and Modernization

  3. Oct 9

    Change Management: Why AI Adoption Stalls and How to Measure Progress

    The episode highlights challenges in AI adoption among employees, with few reporting significant changes in work processes. Key issues include lack of workflow redesign, unclear business strategy alignment, and the rapid evolution of AI complicating stable strategies. Emphasis is placed on measuring actual business value and proactive management for successful integration. Chapters (00:00:00) - Introduction and episode overview(00:01:46) - Research: AI business value and adoption metrics(00:04:34) - Metrics to avoid when measuring AI adoption(00:06:42) - Sandy McCarron: redesigning work, not just adopting tools(00:11:37) - Top-down vs bottom-up strategy lessons from Cisco(00:12:21) - AI as a tool: strategy, alignment, and fear in the workplace(00:16:04) - Martin on uncontrollable pace of AI change(00:19:33) - Derek on workflow redesign and trust building(00:22:30) - Joanne on operational issues and the five whys(00:25:50) - John on system constraints, MCP, and quality metrics(00:30:50) - Joe on leadership, board engagement, and leading by example(00:34:31) - Break recap and upcoming events(00:36:36) - Sandy's new venture and process documentation approach(00:39:22) - Liz on adoption metrics and the Chipotle AI example(00:42:15) - Martin on the value gap between experimentation and board expectations(00:44:00) - Measuring early pilot progress and realistic expectations(00:49:31) - Building change management programs before rollout(00:53:22) - Change management principles and the evolving rules of AI(00:57:35) - Sandy and Liz: surveys, feedback loops, and collaboration cadence(01:01:22) - Closing remarks and upcoming schedule

    Change Management: Why AI Adoption Stalls and How to Measure Progress

  4. Oct 2

    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

  5. Sep 28

    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

  6. 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

  7. 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

  8. 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
See All (46)

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

Information