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Most conversations about AI focus on the technology. David Dean thinks we’re looking in the wrong place. In his new book, An Inbox Between Us, AI and the Reality of Modern Work, he argues that AI is acting like a mirror, revealing the hidden workarounds, decision-making, and human judgment that have always kept organizations running. Today, we’re talking about what leaders can learn from that reflection.
What You’ll Learn in This Episode
Why AI functions as an organizational mirror that exposes hidden workarounds and human judgment
How the majority of workers operate as AI survivalists rather than power users
The hidden cost of the retry tax when over-relying on automated outputs
Why human intuition and lived consequence remain irreplaceable in critical decision-making
How to avoid industrializing existing workplace dysfunction with new technology
Episode Chapters
(00:00) Intro
(00:36) AI as an Organizational Mirror
(05:11) Navigating the Productivity Maxing Trait
(09:01) The AI Survivalist and Adoption Realities
(11:19) Understanding the Hidden Retry Tax
(13:21) How Organizations Rely on Workarounds
(17:20) Tech Problems versus Behavioral Problems
(19:56) Why Human Judgment Outlasts Automation
(23:40) Authenticity as the Ultimate Leadership Skill
(25:19) A Brand That Made Him Smile
About Bill Sherman
David Dean is an author, productivity solution designer, and change management practitioner focused on the intersection of human behavior and emerging technology. In his book, An Inbox Between Us: AI and the Reality of Modern Work, he examines how enterprise technology impacts ground-level teams across HR, finance, and operations. Drawing on years of experience analyzing workplace workflows, David helps organizational leaders navigate digital transformation by focusing on human judgment, authentic leadership, and practical operational discovery.
What Brand Has Made David Smile Recently?
A brand that made David smile recently is Marvel. After taking his son to see the newest Spider-Man movie, he appreciated how the brand continues to craft engaging experiences that bring families together and build lasting memories.
Resources & Links
Connect with David on LinkedIn.Learn more on his website.
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