
The Kennedy-Mighell Report Building an AI Chief of Staff
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Nov 28, 2025 Imagine an AI that acts as your personal Chief of Staff! Dennis and Tom dive into their journey of creating this intelligent assistant to provide strategic support beyond simple scheduling. They discuss the challenges faced, the importance of defining the persona's skills, and the need for an adaptable protocol. Plus, they caution against the pitfalls of adopting new technology in law firms, stressing the need for proper processes and training first. Stay tuned for their tech tips to immediately boost your efficiency!
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Context Beats Basic Scheduling
- Scheduling AIs often fail because they lack deep user context and priorities.
- Building a chief-of-staff persona targets that contextual gap by encoding priorities and expertise.
Define Non-Competencies For Stability
- Combining persona, skills, and explicit non-competencies produces a stable AI role.
- Defining what the AI must not do (non-competencies) narrows errors and keeps behavior consistent.
Make Protocols Reusable With Macros
- Store your chief-of-staff protocol as a reusable source document and invoke it when needed.
- Use TextExpander or similar macros to feed the full protocol into different LLMs for repeatable results.


