Ben “The Automator” Christensen has automated over 300 full-time positions, eliminated 650,000 hours of tasks, and generated over $16 million in savings for companies. He offers fractional CIO and AI officer services as well as custom automation development.
Host: Richard Lowe | Guest: Ben Christensen
Summary
Ben “The Automator” Christensen returns to Leaders and Their Stories for a conversation about AI’s limitations and why the current gold rush mentality around automation might be setting businesses up for expensive failures.
Ben and Richard discuss AI defiance, where AI systems programmed to please users end up in frustrating loops of contradiction and revision. Richard shares a story about spending an entire weekend with Claude developing a marketing plan, only to have the AI tear it apart when asked to identify flaws. They cover context window problems, with Richard describing how a 20-chapter book project degraded into garbage by the end, with characters changing and continuity lost.
The conversation includes a cautionary tale about a startup whose AI agent deleted the entire company database after the human user clicked through a confirmation without thinking. They discuss high-stakes applications where AI failures have real consequences, including lawyers disbarred for submitting AI-generated briefs with fabricated case studies.
Richard predicts a significant correction in the AI market driven by three factors: physical infrastructure limitations with energy and data center heat, economic and political pressure from workforce displacement, and trade disruptions affecting specialized chip supply chains.
They also cover AI-generated resumes that game hiring systems but flood managers with unqualified candidates, the technique of having different AI systems critique each other’s work, and Richard’s “board of directors” prompting technique for getting better results. Richard’s practical advice: treat AI as a smart dog or a small child. It can be useful but requires supervision.
Both agree AI is following the Gartner Hype Cycle and heading toward a trough of disillusionment before settling into productive, realistic applications.
Find Richard Lowe at TheWritingKing.com.