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.

Generative AI can predict how customers will emotionally react to policy changes or marketing messages. Running communications through AI first can prevent the kind of backlash Carnival Cruises experienced by identifying tone-deaf language.

AI expert Andrej Karpathy suggests treating LLMs as simulators, not entities. Instead of asking, "What do you think?", ask, "What would a group of [relevant experts] say?". This elicits a wider range of simulated perspectives and avoids the biases inherent in forcing the LLM to adopt a single, artificial persona.

Unlike human collaborators, an AI lacks feelings or an ego. This means you should be direct, critical, and push back hard when its output isn't right. Frame the interaction as a demanding dialogue, not a polite request. You can also explicitly ask the AI to critique your own ideas from first principles to ensure a rigorous, two-way exchange.

Instead of asking AI for a final answer, use it as a sophisticated focus group. Prompt it to embody different customer personas (e.g., "a left-leaning feminist," "a conservative male") and provide feedback on your messaging from those perspectives. This helps refine copy before market testing.

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.

When dealing with frustrating emails, use an AI agent to first summarize the message into objective bullet points, separating substance from tone. Then, have the AI draft a polite, empathetic response. This preserves your emotional energy for more important work.

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.

Leverage AI to gain external perspectives without meetings. Prompt it to act as a specific persona—like a skeptical CEO, an enthusiastic user, or a New York Times reviewer—to critique your work. This reveals blind spots and strengthens your idea before sharing it.