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  • Evaluating Technologies in the AI Era: Value, Risk, Ecosystem Evaluation

    Evaluating Technologies in the AI Era: Value, Risk, Ecosystem Evaluation
    2026/07/31
    This week's "Coffee with Digital Trailblazers" episode featured industry analyst Maribel Lopez discussing the evaluation of AI technologies. Key topics included the significance of aligning AI selection with business goals, assessing vendor trustworthiness, and managing risks. The panel stressed the need for clear objectives to avoid being overwhelmed by available AI options. Chapters
    • (00:00:01) - When to Select a Technology in the AI Era
    • (00:04:26) - Machine Learning Solution Providers: The Big Three
    • (00:12:40) - Unified Resilience Strategy: Can I Trust The Company?
    • (00:15:46) - 3 Things for Platform Capabilities
    • (00:18:37) - Immature AI Governance
    • (00:22:15) - Change Management: AI and the Business
    • (00:23:42) - Will AI Platform Integrate with Change Management?
    • (00:25:07) - The 3 Questions IT Needs to Ask About AI
    • (00:28:26) - WSJD Live: On the Need for a Continuous AI Stack
    • (00:29:26) - Coffee With Digital Trailblazers
    • (00:30:35) - AI: Short-Term vs. Long Term Value
    • (00:31:38) - Short- and Long-Term Benefits of AI
    • (00:35:34) - What is the AI Debt Trap?
    • (00:37:38) - On the Long Term Use of AI
    • (00:39:31) - On Governance of AI
    • (00:42:35) - AI Agents and Governance
    • (00:46:29) - Martin McGuirk on the Canada-US trade deal
    • (00:47:59) - Can You Be AI-Agent Agnostic?
    • (00:51:21) - The 6 AI Risks
    • (00:53:52) - Top IT Executives: Cross Functional Value
    • (00:54:39) - How to Pick the Right Agents for your Business
    • (00:55:43) - Back-office Strategy: Flexibility, Dependency
    • (00:59:15) - Maribel on AI & Scale
    • (00:59:53) - Coffee With Digital Trailblazers
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    1 時間 2 分
  • Does IT Leadership in the AI Era Require an IT Background Anymore?

    Does IT Leadership in the AI Era Require an IT Background Anymore?
    2026/07/17
    The 180th episode of Coffee with Digital Trailblazers explored whether IT leadership in the AI era necessitates an IT background. Host Isaac Sacolick and guests discussed the importance of IT knowledge for managing AI systems and emphasized clear communication for non-technical leaders to foster trust with IT teams while making informed business decisions. Chapters
    • (00:00:02) - Coffee With Digital Trailblazers
    • (00:00:47) - Does IT Leadership Require an IT Background?
    • (00:01:57) - Does IT Leadership in the AI Era Need an IT Background?
    • (00:05:23) - Does IT Leadership in the AI Era require a IT Background?
    • (00:07:39) - What is important for IT leadership in the AI era?
    • (00:08:59) - Does IT Leadership in the AI Era Need an IT Background?
    • (00:10:57) - CIO Network: The Need for IT Backgrounds
    • (00:11:48) - CIO Network: Is IT Background Important for CIOs?
    • (00:15:38) - CIO Network: The IT Leadership's Role in the AI Era
    • (00:18:37) - CFO vs. CIO: Technology Leadership
    • (00:21:38) - How to Gain Trust with an Interdisciplinary IT Team
    • (00:22:35) - WSJDLive: The Role of CIOs
    • (00:25:11) - How to Build a CIO Leadership Team
    • (00:26:17) - CIO Network: Systems Design and Systems Thinking for the AI Era
    • (00:30:34) - Guarantee the Trust of AI
    • (00:32:54) - CIO Network: How to Build a Connected IT Team
    • (00:34:11) - How to Salvage a Dysfunctional IT Organization
    • (00:36:08) - Coffee With Digital Trailblazers
    • (00:38:01) - Developing IT Acumen
    • (00:38:35) - Clearing the Road of Obstacles
    • (00:44:11) - In the AI era, data governance
    • (00:45:34) - IT Skills vs. Technology
    • (00:46:45) - CIO Network: Knowing Enough to Be Dangerous
    • (00:50:29) - IT Acumen for Business Leaders
    • (00:55:28) - Six Rules for Working Together in the AI Era
    • (00:56:49) - Tech Leadership: Like a Coach
    • (00:58:22) - Coffee With Digital Trailblazers
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    1 時間
  • Reskilling Mid-Career Leaders: What Senior Talent Needs to Stay Relevant

    Reskilling Mid-Career Leaders: What Senior Talent Needs to Stay Relevant
    2026/07/13
    Our discussion focused on reskilling mid-career leaders in the AI era, featuring Dean Cantave. Participants shared experiences on adapting to AI’s impact on careers, emphasizing critical thinking, collaborative leadership, and data governance. Strategies for showcasing leadership skills, moving beyond certifications, and developing new competencies were key points of the conversation. Chapters
    • (00:00:01) - Coffee Hour
    • (00:02:22) - Reskilling mid-career leaders
    • (00:05:00) - "Future of Jobs": Skills, creativity
    • (00:05:59) - Coffee Hour: Change Management in the AI Era
    • (00:08:16) - Dean Cantav on Where to Take Your Career
    • (00:09:28) - Sponsor: AI Reskilling Your Career
    • (00:13:12) - When Will You Need More Skills?
    • (00:16:36) - MSNBC: The Need for Reskilling
    • (00:19:22) - Leveraging AI to Increase Value
    • (00:24:27) - Mid-Career Advice
    • (00:29:23) - Mid-Career Advice for Leaders
    • (00:32:04) - CIO Network: Leadership Skills for the AI Era
    • (00:34:27) - Coffee & IT Leadership in the AI Era
    • (00:36:23) - The Need for Leadership Skills in the AI Era
    • (00:37:40) - Seamless IT: More Competence on Your Resume
    • (00:40:36) - Leaders Need to Enhance Their Skills for the AI Era
    • (00:45:15) - Skills and how do you make them visible and credible?
    • (00:52:16) - Be visible and credible on your resume
    • (00:54:53) - In the Elevator With Joe
    • (00:55:23) - Your Personal Brand
    • (00:58:39) - Rebuilding Your IT Career in the AI Era
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    1 時間 1 分
  • AI Agents for Skeptical Boards: What's Actually Working in Production

    AI Agents for Skeptical Boards: What's Actually Working in Production
    2026/06/26
    In the 178th episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, a panel discussed board perspectives on AI investments. They highlighted challenges like FOMO versus cost concerns, the shift from replacement to augmentation of human roles, and emphasized governance and realistic expectations amid increasing AI budgets despite ROI struggles. Chapters
    • (00:00:01) - Coffee With Digital Trailblazers
    • (00:00:25) - In the Elevator With Tim Crawford
    • (00:01:04) - What Boards Are Thinking About AI Agents
    • (00:03:45) - Examples of ROI from AI Investments
    • (00:05:58) - Board of Digital Ventures: What's Working?
    • (00:06:45) - What's The Board's Take on AI?
    • (00:10:09) - Lighthouse Boards: AI Doesn't Replace People, It Augments
    • (00:12:07) - The Most Promising Agent Path to Value
    • (00:14:35) - Understanding the true costs of AI
    • (00:18:36) - Board perspectives on AI
    • (00:22:19) - boards are conflicted on risk and reward
    • (00:23:50) - Robots and the Board of Directors
    • (00:27:55) - Board of Directors on AI and Cost
    • (00:29:19) - Board of Directors: The FOMO around AI
    • (00:34:50) - CIO Network: The Importance of AI Decisions
    • (00:36:20) - Coffee With Digital Trailblazers
    • (00:37:33) - AI Boards: Real Expectations
    • (00:42:30) - Board of Governance: AI Governance
    • (00:47:01) - AI's Disparity
    • (00:49:46) - A Sense of Value on the Board
    • (00:53:47) - CIO Network: The Future of IT Strategy
    • (00:55:06) - Five Rules for AI Risk & Compliance
    • (00:57:09) - Six Rules for Differentiable Value in AI
    • (00:59:21) - A Day in the Life of AI with Digital Trailblazers
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    1 時間 1 分
  • From Idea to Impact: Shrinking Innovation Cycles With AI

    From Idea to Impact: Shrinking Innovation Cycles With AI
    2026/05/29
    Isaac Sacolick hosted a discussion on innovation in the AI era. Key insights highlighted the convergence of roles, efficiency of smaller DevOps teams, and the transformative impact of AI coding tools. Despite advancements, challenges in governance and quality assurance in production remain significant, necessitating careful management and strategic oversight. Chapters
    • (00:00:01) - Coffee With Digital Trailblazers
    • (00:02:16) - The 3 Things Driving Faster Innovation Cycles
    • (00:06:20) - Discussing Innovation in the Workplace
    • (00:07:28) - Coffee With Digital Trailblazers: Role Convergence
    • (00:09:40) - Role Conversion and AI-based Innovation
    • (00:10:58) - What's Really Helping Us Accelerate with AI?
    • (00:14:29) - What's Accelerating the Company's Product Cycle?
    • (00:17:59) - A couple of thoughts on the AI Hype Cycle
    • (00:22:00) - What's Driving the Acceleration of AI in C&C?
    • (00:23:46) - The role of the AI Architect
    • (00:31:21) - Upcoming Episodes
    • (00:34:03) - The CIO Network: Digital Trailblazers
    • (00:36:26) - AI Creativity and the Need for Senior People
    • (00:40:44) - What's Driving the Investment in AI?
    • (00:44:00) - Role the Architect in the 21st Century
    • (00:44:34) - Small to Medium Businesses
    • (00:46:00) - Secure IT: Governance of AI Innovation
    • (00:50:38) - Change Management in the World of AI
    • (00:56:50) - CIO Network: On the Need for Scalability, Security &
    • (00:58:10) - CIO Network: AI Implementation Success stories
    • (01:00:00) - AI Coffee
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    1 時間 2 分
  • Mental Health in the AI Era: Easing Fears About the Future of Work

    Mental Health in the AI Era: Easing Fears About the Future of Work
    2026/05/08
    The episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, addressed mental health in the context of AI's impact on employment. The panel emphasized the importance of transparency, psychological safety, and ongoing learning. Key insights included the need for ethical leadership and structured AI wellness programs to ease employee concerns and enhance organizational culture. Chapters
    • (00:00:00) - Coffee With Digital Trailblazers
    • (00:00:57) - CAKE: AI Burnout in the Security Industry
    • (00:02:24) - Coffee With Digital Trailblazers
    • (00:05:24) - How Do You Communicate AI's Impact on Your Roles?
    • (00:06:28) - Top Executives: The Future of AI
    • (00:09:15) - The Future of Advertising With AI
    • (00:10:27) - The Communication Challenge of AI
    • (00:13:55) - Cybersecurity Risk Management: AI and the Future of Work
    • (00:15:54) - 74% of CEOs Think Their Jobs Are at Risk in AI
    • (00:20:50) - How to communicate AI's transformative opportunity
    • (00:22:56) - Post-Vacation Break
    • (00:23:13) - A Team's Transformation With AI
    • (00:27:19) - Mental Health in the AI Era
    • (00:29:19) - What is psychological safety in our teams?
    • (00:31:09) - Harness Your Skeptics: The Future of Creativity
    • (00:32:24) - How to Create Psychological Safety
    • (00:33:56) - Entry-level Jobs Being Replaced With AI
    • (00:37:30) - Creating Psychological Safety for AI Workers
    • (00:40:15) - Physical Safety and Psychological Safety
    • (00:44:41) - Do We Need a Retirement Plan for AI?
    • (00:47:12) - On Intelligence and Psychological Safety
    • (00:50:58) - What Healthy AI Adoption Looks Like
    • (00:54:41) - What Is Healthy AI Adoption?
    • (00:59:17) - A message about mental health in the AI era
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    1 時間
  • AI Coding Competencies: Hype, Realities, and the Future

    AI Coding Competencies: Hype, Realities, and the Future
    2026/04/17
    In a recent episode of Coffee with Digital Trailblazers, Isaac Sacolick led a discussion on AI coding competencies with experts Dave Bachman and David Cassel. They examined AI development tools, emphasizing effective requirement engineering, security considerations, and the challenges of achieving artificial general intelligence (AGI), while spotlighting risks associated with AI-generated code. Chapters
    • (00:00:01) - Coffee With Digital Trailblazers: How AI Is
    • (00:01:26) - AI Coding Competencies
    • (00:05:39) - Dave Bachmann on the Future of Machine Learning
    • (00:11:08) - Coffee With Digital Trailblazers: AI Coding
    • (00:18:39) - Citizen Development with Vibe Coding
    • (00:22:22) - How To Manage the AI Code Development
    • (00:26:40) - Dave and Joanne on Building AI Apps
    • (00:31:19) - The Importance of Writing Requirements
    • (00:32:31) - Coffee with Digital Trailblazers
    • (00:34:25) - Cogeneration and AI on C#
    • (00:37:14) - Does a Software Engineer Have Digital Sovereignty?
    • (00:40:06) - Joe on the Co-Generation
    • (00:40:30) - Will AI Replace the Devs?
    • (00:43:41) - The Need for AI-related Skills
    • (00:47:00) - The Future of Code is Human
    • (00:48:03) - Best Advice for Q&A Tools for Agentix
    • (00:53:31) - Amino vs. AI DevOps
    • (00:55:22) - CIO Network: The Future of AI DevOps
    • (00:56:26) - Six Rules for Leading in the AI World
    • (00:57:44) - Hype around AGI
    • (00:58:45) - Artificial General Intelligence (AGI)
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    1 時間 4 分
  • Developing Your Personal Brand: Best Practices From Thought Leaders

    Developing Your Personal Brand: Best Practices From Thought Leaders
    2026/04/10
    This episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, features a discussion on personal branding and thought leadership in technology. Key speakers shared their experiences and best practices, emphasizing authenticity, consistency, and gradual progress in building a personal brand, likening the journey to a marathon rather than a sprint. Chapters
    • (00:00:01) - Coffee With Digital Trailblazers
    • (00:01:17) - A toast to Thought Leaders at the Coffee Hour
    • (00:03:20) - A Taste of the Blog
    • (00:04:48) - Lead From The trenches: My
    • (00:10:07) - How to Build a Brand Through Digital Speaking
    • (00:12:20) - CIO Network: The First Moment
    • (00:17:38) - CIO Confessions: Personal Brand
    • (00:21:12) - Speaking Out Loud
    • (00:23:14) - Cyber Resilience: The 5 Ps
    • (00:25:08) - Cyber Resilience: The challenge of communicating your message
    • (00:28:59) - Have You Got a Brand?
    • (00:34:19) - Developing Your Personal Brand
    • (00:36:11) - Coffee Hour for Introverts
    • (00:40:50) - Heather's Advice for Publishers
    • (00:42:48) - How to Build a Brand on LinkedIn
    • (00:47:16) - How to Build a Personal Brand
    • (00:49:54) - Caffeine Hour: Nora's Journey
    • (00:50:32) - What are some of the realities people should have as they're embark
    • (00:53:59) - Derek Martin on Spelling Your Brand
    • (00:57:05) - Writing for Social Networking
    • (00:57:43) - How to Build a Brand with Your Friends
    • (00:58:27) - A Week in the Life of Band
    • (00:58:50) - AI Coding Competencies
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    1 時間