Coffee with Digital Trailblazers
The Coffee With Digital Trailblazers is a LinkedIn Live Event, and we meet just about every Friday at 11am ET. Every week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate.
We discuss topics for digital transformation leaders, i.e., Digital Trailblazers, who are driving business value from innovation, culture transformation, agile collaboration, and change management across their organizations.
Upcoming Episodes
- 11/13 – AI’s 2027 Reality Gap: Big Expectations, Tight Supply, Hard Choices
- 11/20 – AI for Social Good: Doing More With Less When the Mission Can’t Wait
- 11/27 – No Session – Happy Thanksgiving!
Four Ways to Listen!
- Join the live event on LinkedIn Fridays at 11am ET
- See the Whiteboards and listen here at the StarCIO Digital Trailblazer Community (episode list below!)
- Subscribe on Apple Podcasts, Amazon Podcasts, and Spotify (selected episodes)
This Week’s Episode
Speakers
- Host – Isaac Sacolick
- Digital Trailblazers – Derrick Butts, Martin Davis, Joanne Friedman, John Patrick Luethe, Liz Martinez, Heather May, Joseph Puglisi
Discussion
- Big Expectations: Where have you seen the biggest gap between what leaders expected in 2026 from AI and innovation versus what got delivered?
- Tight Supply: How should Digital Trailblazers plan AI and other innovation work when compute costs, infrastructure availability, and evolving skill requirements can change mid-year?
- Hard Decisions: What steps should Digital Trailblazers take in planning and delivering initiatives so that, if supply tightens, their work is less likely to be impacted?
Research
About the Coffee With Digital Trailblazers
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Recent Episodes
Watch the full episodes on LinkedIn
- 6/26 – AI Agents for Skeptical Boards: What’s Actually Working in Production
- 7/10 – Reskilling Mid-Career Leaders: What Senior Talent Needs to Stay Relevant
- 7/17 – Does IT Leadership in the AI Era Require an IT Background Anymore?
- 7/24 – FinAI & Managing AI Costs: Innovation, Production, and Lifecycle
- 7/31 – Evaluating Technologies in the AI Era: Value, Risk, Ecosystem Evaluation
- 8/7 – Networking in the AI Era: A Guide for Digital Transformation Leaders
- 8/14 – Beyond Legacy Processes: Engineering the High-Velocity Enterprise
- 8/21 – Shadow AI at Work: Real Risks, Practical Guardrails, Hidden Innovation
- 8/28 – SaaS, Cloud, and AI Contracts: Where Technology Leaders Lose Leverage
- 9/11 – The Hidden Cost of Confident AI: Semantics, Guardrails, and the Context Layer
- 9/18 – Tech Budget 2027: AI Bets to Fund; What IT and Security to Protect
- 9/25 – Getting Hired in the AI Era: Stand Out, Signal Judgment, Land the Role
- 10/2 – Vibe, Buy, or Automate? Deciding How to Build AI Agents
- 10/9 – Change Management: Why AI Adoption Stalls and How to Measure Progress
- 10/16 – AI Infrastructure Debt: Strategies for Capacity, Resiliency, and Modernization
- 10/23 – Finishing Strong: How Digital Leaders Close Out the Year
- 10/30 – AI Agent Strategy: Human Augmentation vs. In-the-Middle vs. Agentic?
- 11/6 – Planning 2027: What Practices are Transformation Leaders Prioritizing?
Coffee With Digital Trailblazers – Themes
We cover many topics, but have several recurring themes:
- Accelerating Transformation – Developing force multipliers in digital transformation that accelerate the delivery of multiple business values
- AI Era Transformation – Looking at what AI can deliver in the short and longer-term, and what Digital Trailblazers should be leading to deliver AI impacts
- Shaping Tomorrow – About emerging technologies, their business opportunities, disruptive threats, and how Digital Trailblazers can accelerate innovation
- Culture Transformation – Leadership and disciplines that drive culture change, including agile, design thinking, product management, and change management
- Cultivating Digital Trailblazers – Hiring, retaining, mentoring, and coaching Digital Trailblazers – and also how Digital Trailblazers find opportunities, expand their responsibilities, and plan their careers.
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Recordings: Coffee with Digital Trailblazers
More Podcast Episodes are available with a StarCIO Digital Trailblazer Community Subscription
