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Managing Skepticism: Balancing Tradition and Technology with AI episode artwork

Sep 22, 2026 49 min

Managing Skepticism: Balancing Tradition and Technology with AI

from How Many CTOs

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how AI is changing software engineering referencing Kent Beck's idea that AI makes much existing knowledge less useful while making a smaller portion far more valuable. They describe teams collaborating through "cohorts" of AI agents for PR review and adversarial checking, and debate whether engineers will be evaluated on agent quality versus their ability to direct and manage agents like a driver or jockey. Scott shares TaskRabbit's approach to shifting from organic AI adoption to "systemic usage" using an AI maturity matrix, gap analysis, and incremental rollout of agents (code review, security, architecture) with a six-week versioned cadence to help the whole organization keep up. They address skepticism, incentives in for-profit organizations, and the rapid pace of AI tooling innovation. 00:00 Cold Open 00:28 Podcast Kickoff 01:22 Uncle Bob Clip Reactions 02:16 Kent Beck Tease 03:39 Engineers With Agent Teams 05:19 Prompting vs Building Agents 10:16 Managing Agents Like Juniors 13:08 Handling AI Holdouts 17:20 Why Build Beats Craft 19:26 Software as Puzzle Pieces 21:38 TaskRabbit AI Maturity Plan 23:56 From Organic to Systemic 26:19 Six Week Change Cadence 27:11 Handling Corporate Agenda Fears 29:02 Why AI Becomes Inevitable 33:28 Leading With Growth Mindset 35:29 Imperfect Tools Fair Comparisons 38:54 Innovation Pace And Morale 42:34 Dark Factory And SDLC Evolution 47:12 Outages CD ROMs And Wrap Up 49:25 Closing Credits Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/ Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/ #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding

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This episode was published on September 22, 2026.

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