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.

The best use of AI in coaching is as a tool for skill practice, not a human replacement. It offers a safe, low-stakes environment for leaders to rehearse challenging scenarios, like difficult conversations, and receive immediate feedback without the judgment of a human observer.

Zapier built an AI coach that analyzes meeting transcripts to provide feedback based on company values and frameworks. This automates cultural reinforcement, normalizes constructive criticism, and ensures leaders consistently model desired behaviors, scaling what is typically a manual process.

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.

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.

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.

Instead of spending hours agonizing over how to deliver constructive criticism, Lindsay Carter used AI. She inputted her concerns for a new assistant and prompted the AI to act as an expert. It generated a clear, structured, and helpful email in five minutes, demonstrating AI's power for improving leadership efficiency and communication.

An automated workflow analyzes call transcripts and sends immediate, private feedback to the sales or CS rep on what they did well and where they can improve. This democratizes high-quality coaching, evens the playing field across managers of varying skill, and empowers motivated reps to upskill faster.

A marketing leader uses her personalized GPT to coach junior writers more efficiently. She inputs shorthand notes on their work, and the AI structures it into coherent feedback that explains the reasoning behind the edits. This transforms a time-consuming rewrite into a scalable coaching opportunity.