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To improve the quality of executive one-on-ones, Progeny created a custom GPT that mimicked its CEO's detail-oriented questioning style. This allowed leaders to pressure-test their ideas and show up better prepared for time-poor, high-stakes conversations.
Create distinct AI agents representing key executives (e.g., CEO, CMO, CSO). By posing strategic questions to each, you can simulate how different departments might react, identify potential misalignments in priorities, and refine proposals before presenting them to real stakeholders.
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.
Build a skill that simulates your executive team based on their known goals and priorities stored in your AI's intelligence layer. This allows you to get critical feedback and find holes in your thinking before presenting, increasing your chances of success.
Power dynamics often prevent leaders from receiving truly honest feedback. By implementing AI "coaching bots" in meetings, executives can get objective critiques of their performance. The AI acts as an "infinitely patient coach," providing valuable insights that colleagues might be hesitant to share directly.
By building a custom GPT with deep company context, a CEO can compress hundreds of hours of research, analysis, and document creation into a 10-15 hour collaborative session, generating 95% of the final strategic output.
Go beyond using AI for simple research. Feed it public data about a specific executive (from blogs, interviews, etc.) and instruct it to act as that person. This allows you to practice conversations, refine arguments, and master their specific communication style before a critical meeting.
Instead of using AI as a compliant assistant, program it to be a challenging 'sparring partner.' Ask it to find holes in your logic or anticipate all the critical questions your CEO might ask. This transforms it from a content generator into a powerful strategic tool for preparation.
Before a high-stakes meeting, train a large language model on transcripts of that executive's previous product reviews. You can then run your pitch or PRD through this custom AI to anticipate specific pushback, identify weaknesses in your proposal, and better prepare for the conversation.
Markup AI's CEO built AI profiles for figures like Steve Jobs. Before board meetings, he runs his deck by this "fantasy board" to get instant, diverse feedback, effectively bringing expertise into the room that isn't physically there.
To scale the CEO's feedback, his EA created a custom GPT trained on his feedback style, strategy docs, and company norms. Team members use this 'CEO clone' to stress-test their proposals before official review, improving document quality and saving executive time.