An executive created a custom AI agent to handle repetitive tasks like meeting prep, calendar triage, and email. This "chief of staff" provides analysis, suggests delegations, and even offers blunt feedback, demonstrating how AI can be personalized to augment executive functions.

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AI transforms the Executive Assistant role from tactical execution to strategic system design. By automating repetitive tasks, EAs can focus on higher-leverage activities like building AI agents, culture-reinforcement tools, and scalable feedback systems for the entire organization.

Business owners are overwhelmed by AI terminology. A consultant can create a personalized GPT ecosystem using their unique preferences, goals, and workflows. This service turns an executive's operational knowledge into valuable intellectual property, packaged as custom system prompts and GPTs they can use daily.

Webflow's CPO uses a custom set of AI agents built with Claude and Cursor to analyze her calendar for delegation opportunities and triage her inbox by archiving junk, flagging important emails, and drafting replies. This offloads significant cognitive and administrative load from the executive.

Generic use cases fail to persuade leadership. To get genuine AI investment, build a custom tool that solves a specific, tangible pain point for an executive. An example is an 'AI board member' trained on past feedback to critique board decks before a meeting, making the value undeniable.

Instead of relying on one-off prompts, professionals can now rapidly build a collection of interconnected internal AI applications. This "personal software stack" can manage everything from investments and content creation to data analysis, creating a bespoke productivity system.

An Executive Assistant at Zapier built an AI agent that automates her weekly meeting prep. The agent researches external attendees, checks the CRM and internal comms for context, and delivers a digest and tasks. This saves hours of manual work and ensures thorough preparation.

To get truly honest feedback, Webflow's CPO programmed her AI chief of staff to be "mean." The AI delivers a "brutal truth" section, criticizing her for spending time on tasks below her role. This demonstrates how AI can serve as an unflinching accountability partner, providing feedback humans might hesitate to give.

Go beyond using AI for research by codifying your North Star, OKRs, and strategic goals into a personalized AI agent. Before important meetings, use this agent as a 'thought partner' to pressure-test your ideas, check for alignment with your goals, and identify blind spots. This 10-minute exercise dramatically improves meeting focus and outcomes.

Your calendar is the foundation of your execution system. Use AI to scan your schedule, find recurring blocks for deep work on key goals, and automatically suggest rescheduling conflicts. This moves AI from a passive assistant to an active agent that defends your most valuable resource: your time.

Unable to secure budget for a human chief of staff, Webflow's CPO built her own using AI agents. This system automates complex, recurring tasks like podcast research and data prep, demonstrating how executives can use AI to gain significant personal leverage without increasing headcount.

Webflow's CPO Built a Personal "AI Chief of Staff" to Manage Her Workflow | RiffOn