CTO Unfiltered | Digital Transformation & AI Impact

Mike Schubert | Technology Executive & AI Impact Leader
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If you're on the CTO track, you already know the technology isn't the hard part. CTO Unfiltered is for technology leaders navigating AI transformation, organizational complexity, and the gap between what technology promises and what companies can actually absorb. Hosted by Mike Schubert — VP of Technology, 30-year practitioner, and someone who's still doing the job. No hype. No punditry. Just the practitioner lens.

Episodes

  1. 6d ago

    Ep. 4 - When Agents Build the App, Who Builds the Engineer?

    We're at an inflection point. Agentic AI can now produce code faster than most teams can validate it — and some companies are already using that as justification to skip building junior developer pipelines altogether. In this episode, Mike makes the case that this is one of the most consequential mistakes tech leaders can make right now. Software engineering was never just typing. It was always about judgment: understanding requirements, reasoning about edge cases, thinking through security implications, mapping code to business context. AI can augment the typing. It cannot yet replace the thinking. KEY TOPICS - The "it worked on my machine" problem at AI scale — hallucinated packages, test cases that return true, code that compiles but doesn't function - The Waterfall → Agile transition as a reminder that articulating requirements has always been the hard part of software - Why eliminating junior developer pipelines creates a knowledge time bomb - How AI-generated vulnerabilities are correlated, not random — one found pattern becomes a scannable attack surface across thousands of repositories - The 14-day median dwell time + 22-second hand-off window from Mandiant M-Trends 2026 - The WordPress plugin backdoor: patience as a supply chain attack vector - Why "trust" must be a continuous evaluation, not a one-time event - Judgment as the irreplaceable core of software engineering SOURCES & ARTICLES REFERENCED 1. Mandiant M-Trends 2026   Median dwell time: 14 days. Time from initial access hand-off to secondary threat: 22 seconds.   https://cloud.google.com/blog/topics/threat-intelligence/m-trends-2026   Coverage: https://complexdiscovery.com/twenty-two-seconds-to-hand-off-inside-mandiants-m-trends-2026-findings/ 2. Georgia Tech "Bad Vibes" — AI-Generated Code Vulnerabilities   43,000+ advisories scanned. 18 confirmed cases H2 2025, 56 in Q1 2026 (35 in March). True count: 400–700.   https://research.gatech.edu/bad-vibes-ai-generated-code-vulnerable-researchers-warn   https://scp.cc.gatech.edu/external-news/bad-vibes-ai-generated-code-vulnerable-researchers-warn 3. WordPress "Essential Plugin" Supply Chain Backdoor (April 2026)   30+ plugins purchased on Flippa, backdoor planted, activated 8 months later.   https://thenextweb.com/news/wordpress-plugins-backdoor-supply-chain-essential-plugin-flippa-2   https://www.techrepublic.com/article/news-malicious-wordpress-plugins-backdoor-april-2026/ Questions or topics for a future episode? Reach the show at producer@ctounfiltered.fm. Mike Schubert is VP of Technology at Unum Group. The views expressed in this episode are Mike's own and do not represent the views of his employer.

    21 min

  2. Apr 20

    EP. 3 - Building Systems that Build People

    Elite performance in engineering organizations isn't about finding rock stars — it's about building the systems that produce them. In this episode, Mike Schubert breaks down two Harvard Business Review research pieces that share a single underlying thesis: team performance is a design problem, not a talent problem. From the three levers that produce organizational excellence (talent, team, routine) to the learning velocity habits that keep teams improving in periods of rapid change, Mike applies these frameworks to the reality of leading large engineering teams in regulated, high-stakes environments. Then: a sharp pivot. The same principle applies to AI. The "human in the loop" is the foundational promise of responsible AI deployment — but new research from Boston Consulting Group reveals a structural flaw. When pushed back on, LLMs don't reconsider. They argue. Understanding this changes how you build AI governance into your organization. What We CoverWhy heroics don't scale — and what doesThe three levers of organizational excellence: talent, team, and routineWhat "moments that matter" actually look like inside an engineering org (pull requests, sprint reviews, postmortems, incident retrospectives)How to expose high-potential engineers to decisions 1-3 levels above their current roleThree habits that build learning velocity: run more experiments, make curiosity contagious, ask what people are stuck onWhy polished status updates are killing your signal — and what to do insteadLLMs and rhetorical manipulation: what the BCG research actually found"An impenetrable fortress of data and rhetoric" — what that means for your AI governance modelThe human in the loop only works if the human hasn't already been talked out of itSources & Links"How to Turn Individual Talent into Organizational Excellence" — James Fulton & Todd Warner, HBR, March 2026: https://hbr.org/2026/03/how-to-turn-individual-talent-into-organizational-excellence"3 Ways to Build a Superteam" — HBR Management Tip, April 13, 2026: https://hbr.org/tip/2026/04/3-ways-to-build-a-superteam"LLMs Are Manipulating Users with Rhetorical Tricks" — Tom Stackpole, HBR, March 18, 2026: https://hbr.org/2026/03/llms-are-manipulating-users-with-rhetorical-tricksImage: Stephen Curry, Warriors vs. 76ers, January 2, 2025 — NBA.com/Warriors:https://www.nba.com/warriors/news/gameday-recap-20250102DisclaimerThe views expressed in this content are those of Mike Schubert and are not meant to represent those of his employer.

    30 min

  3. Mar 30

    Ep. 2 - Agents are Everywhere. Now What?

    What does it mean to lead through uncertainty when the technology underneath you is moving faster than your governance, your metrics, and your comfort level? Mike Schubert digs into four things: Harvard research on why sharing uncertainty builds trust; Microsoft Agent 365 and the shadow agent problem; IBM Bob 1.0 for the COBOL/RPG world; and Jensen Huang's token consumption metric. Three stories, one thread: agents proliferating faster than governance, faster than measurement, and faster than most leaders' comfort level. Have feedback or a question you'd like to have answered on the air? Email producer@ctounfiltered.fm Timestamps0:00 - Intro & episode overview1:30 - Segment 1: When to Open Up at Work (Leslie John / HBR)7:07 - Segment 2: Microsoft Agent 365 & agent sprawl14:17 - Segment 3: IBM Bob & the ghost of Microsoft Bob16:28 - Segment 4: AI ROI - are we measuring the right thing?21:56 - Outro Sources & LinksSegment 1 - When to Open Up at WorkHBR: When to Open Up at Work (Leslie John, Feb 2026)Book: Revealing by Leslie John - Riverhead Books, Feb 26 2026Segment 2 - Microsoft Agent 365Microsoft 365 Blog - Powering Frontier Transformation (Mar 9 2026)Copilot Studio - 6 Core Capabilities to Scale Agent AdoptionMicrosoft Agent 365 (GA May 1 2026)Segment 3 - IBM BobIT Jungle: IBM Gets Bob 1.0 Off The Ground (Mar 2 2026)IBM BobMicrosoft Bob (1995) - WikipediaSegment 4 - AI ROIAll-In Podcast: Jensen Huang at GTC 2026

    23 min

  4. Mar 26

    Episode 1 - You Don't Need Another Tech Podcast. Here's Why I Made One Anyway

    Most tech podcasts talk about technology. This one talks about what actually makes or breaks a technology leader: people, change, and the gap between what organizations want and what they can absorb. In this opening episode, Mike lays out his case — who he is, what this show is, and why the conversation he wanted to have didn't exist yet. Takeaways • The technology is rarely the hard part — leading the people and the change around it is. CTO Unfiltered exists because the practitioner perspective has been missing from the conversation.

    9 min
  • 4 Episodes

About

If you're on the CTO track, you already know the technology isn't the hard part. CTO Unfiltered is for technology leaders navigating AI transformation, organizational complexity, and the gap between what technology promises and what companies can actually absorb. Hosted by Mike Schubert — VP of Technology, 30-year practitioner, and someone who's still doing the job. No hype. No punditry. Just the practitioner lens.

Information

  • Creator
    Mike Schubert | Technology Executive & AI Impact Leader
  • Years Active
    2K
  • Episodes
    4
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    Clean
  • Copyright
    © 2026 Mike Schubert | Technology Executive & AI Impact Leader