Build an AI management second brain

Dave Kline and Marsden Kline are pitching a new management tool: a personal AI that acts like a chief of staff and remembers how you lead. (maven.com) Their Maven workshop, scheduled for April 29, 2026, costs $500 and runs 3.5 hours. The course page says managers will build a “Management Second Brain” that knows their team, decisions and leadership patterns. (maven.com 1) (maven.com 2) The idea is simple: feed notes, frameworks and recurring situations into one system, then query it before one-on-ones, reviews and decisions. The workshop agenda says the AI should also generate briefs, meeting prep and weekly digests on a schedule. (maven.com) Kline frames the problem as “management amnesia” — lessons from past hires, feedback cycles and org changes get lost in scattered notes and memory. The course page says participants will build a five-folder structure and a maintenance engine that updates the system after each one-on-one and decision. (maven.com) The pitch is less about a better chatbot than a reusable operating system for managers. Maven’s description says the AI will reference a manager’s own playbook, plus frameworks such as Objectives and Key Results and McKinsey 7-S, each time it coaches or prepares them. (maven.com) That language matches a broader enterprise shift now being marketed as “intent-first” work. In a March 12 post, Microsoft said companies are moving from software people navigate themselves toward agents that can carry out goals across systems while apps become systems of record and governance. (microsoft.com) In that model, the manager’s job changes too. The human sets priorities, constraints and judgment; the software handles briefing, follow-up, retrieval and parts of execution. (microsoft.com) (maven.com) Kline is already selling adjacent training under the label “AI-powered leader.” His Maven instructor page lists courses including “MGMT Accelerator: AI-Enhanced Leadership” and a live lesson called “The 5 Non-Negotiable Skills of the AI-Powered Leader.” (maven.com) The immediate claim is narrower than replacing managers. It is that a leader with 25 years of notes, 100-plus playbook entries and a weekly update ritual can turn that history into a system that gets more useful at weeks 4, 12 and 26. (maven.com) What happens next is less a product launch than a management experiment. If the idea sticks, the “chief of staff” may stop being a senior hire and start becoming a workflow managers build for themselves. (maven.com)