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Enterprise Connect
March 10-12, 2026
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AI Agents: Proceed with Caution

This interview between tech legend Guy Kawasaki and Meredith Whittaker, president of encrypted messaging app Signal drew some attention recently among the AI-skeptical. At the 50-minute mark of the linked video, Whittaker raises the issue of Agentic AI, and describes the multiple points of vulnerability encountered in a single agentic transaction, positing a scenario where the agentic AI looks up a concert, books a ticket, schedules it in your calendar, and messages your friends to tell them you’re attending. Such transactions would require accessing your browser, credit card information, calendar, and messaging app, which creates, according to Whittaker, “a profound issue with security and privacy.” Whittaker oversees an app devoted to placing security above all other considerations, so it’s not surprising that she’d raise this alarm. Wired called her “one of the world’s most prominent tech critics,” and her own view can be inferred from her offhand remark in the video above about agentic AI letting users “put our brains in a jar” while the agentic AI serves as a “magic genie bot that’s going to take care of the exigencies of life.” Nevertheless, I think it’s incumbent on the technology providers, whether enterprise- or consumer-focused, to explain in detail why users shouldn’t be concerned about the level of access Whittaker describes, and the potential for catastrophic security breaches it threatens. Yet there are signs that users aren’t worried enough about this.