Leaders are often trapped "inside the box" of their own assumptions when making critical decisions. By providing AI with context and assigning it an expert role (e.g., "world-class chief product officer"), you can prompt it to ask probing questions that reveal your biases and lead to more objective, defensible outcomes.

AI models are trained to be agreeable, often providing uselessly positive feedback. To get real insights, you must explicitly prompt them to be rigorous and critical. Use phrases like "my standards of excellence are very high and you won't hurt my feelings" to bypass their people-pleasing nature.

Don't let performance reviews sit in a folder. Upload your official review and peer feedback into a custom GPT to create a personal improvement coach. You can then reference it when working on new projects, asking it to check for your known blind spots and ensure you're actively addressing the feedback.

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.

Rehearse difficult conversations by having an AI adopt the persona of your boss, partner, or employee. This allows you to practice your approach, refine your messaging, and anticipate reactions in a safe environment, increasing your confidence and effectiveness for the real discussion.

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.

Standard AI models are often overly supportive. To get genuine, valuable feedback, explicitly instruct your AI to act as a critical thought partner. Use prompts like "push back on things" and "feel free to challenge me" to break the AI's default agreeableness and turn it into a true sparring partner.