To improve his management style, Wilkinson uses an AI tool to refine his communication. He can dictate his raw, unfiltered thoughts about an employee's performance, and a prompt called "a good boss" rephrases it into a toned-down, mature, and effective message.

Related Insights

Instead of replacing managers, AI can act as a 'bionic enhancement' or a mirror. It provides objective feedback on communication, helping overwhelmed leaders scale their human skills like empathy and listening in an increasingly complex remote work environment.

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.

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.

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.

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.

The skills required for effective AI prompting—providing clear roles, context, and constraints—are directly transferable to human interaction. By learning to communicate with machines, marketers inadvertently train themselves in the fundamentals of clear delegation and management.

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.

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.

Use a conversational AI like ChatGPT as a personal executive coach. After many conversations, it learns your thought patterns and can provide objective, articulate feedback on your working style and flaws. This can be used to generate a highly accurate 'how to work with me' document for your team.