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.

The most powerful use of AI for business owners isn't task automation, but leveraging it as an infinitely patient strategic advisor. The most advanced technique is asking AI what questions you should be asking about your business, turning it from a simple tool into a discovery engine for growth.

Instead of asking AI for answers, leaders can prompt it to be a "strategic thought partner" that asks critical questions one by one. This process helps refine strategies for board meetings by forcing the leader to anticipate and address tough questions about revenue impact and core business concerns.

A powerful, practical application of AI for leaders is to treat it as a multidisciplinary advisor or "Co-CEO." This framing allows for high-level collaboration on strategic planning, tapping into AI's expertise across finance, legal, HR, and operations.

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.

Default AI models are often people-pleasers that will agree with flawed technical ideas. To get genuine feedback, create a dedicated AI project with a system prompt defining it as your "CTO." Instruct it to be the complete technical owner, to challenge your assumptions, and to avoid being agreeable.

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.

A leader's most valuable use of AI isn't for automation, but as a constant 'thought partner.' By articulating complex business, legal, or financial decisions to an AI and asking it to pose clarifying questions, leaders can refine their own thinking and arrive at more informed conclusions, much like talking a problem out loud.