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CTO Unfiltered | Digital Transformation & AI Impact

CTO Unfiltered | Digital Transformation & AI Impact

By: 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.

2026 Mike Schubert | Technology Executive & AI Impact Leader
Economics Management Management & Leadership
Episodes
  • Ep. 4 - When Agents Build the App, Who Builds the Engineer?
    Jun 26 2026


    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.

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    21 mins
  • EP. 3 - Building Systems that Build People
    Apr 20 2026

    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 Cover
    • Why heroics don't scale — and what does
    • The three levers of organizational excellence: talent, team, and routine
    • What "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 role
    • Three habits that build learning velocity: run more experiments, make curiosity contagious, ask what people are stuck on
    • Why polished status updates are killing your signal — and what to do instead
    • LLMs and rhetorical manipulation: what the BCG research actually found
    • "An impenetrable fortress of data and rhetoric" — what that means for your AI governance model
    • The human in the loop only works if the human hasn't already been talked out of it
    Sources & 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-tricks
    • Image: Stephen Curry, Warriors vs. 76ers, January 2, 2025 — NBA.com/Warriors:https://www.nba.com/warriors/news/gameday-recap-20250102
    Disclaimer

    The views expressed in this content are those of Mike Schubert and are not meant to represent those of his employer.

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    30 mins
  • Ep. 2 - Agents are Everywhere. Now What?
    Mar 30 2026

    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

    Timestamps
    • 0:00 - Intro & episode overview
    • 1:30 - Segment 1: When to Open Up at Work (Leslie John / HBR)
    • 7:07 - Segment 2: Microsoft Agent 365 & agent sprawl
    • 14:17 - Segment 3: IBM Bob & the ghost of Microsoft Bob
    • 16:28 - Segment 4: AI ROI - are we measuring the right thing?
    • 21:56 - Outro

    Sources & LinksSegment 1 - When to Open Up at Work
    • HBR: When to Open Up at Work (Leslie John, Feb 2026)
    • Book: Revealing by Leslie John - Riverhead Books, Feb 26 2026
    Segment 2 - Microsoft Agent 365
    • Microsoft 365 Blog - Powering Frontier Transformation (Mar 9 2026)
    • Copilot Studio - 6 Core Capabilities to Scale Agent Adoption
    • Microsoft Agent 365 (GA May 1 2026)
    Segment 3 - IBM Bob
    • IT Jungle: IBM Gets Bob 1.0 Off The Ground (Mar 2 2026)
    • IBM Bob
    • Microsoft Bob (1995) - Wikipedia
    Segment 4 - AI ROI
    • All-In Podcast: Jensen Huang at GTC 2026
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    23 mins
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