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.

A powerful workflow is to explicitly instruct your AI to act as a collaborative thinking partner—asking questions and organizing thoughts—while strictly forbidding it from creating final artifacts. This separates the crucial thinking phase from the generative phase, leading to better outcomes.

Instead of spending time trying to craft the perfect prompt from scratch, provide a basic one and then ask the AI a simple follow-up: "What do you need from me to improve this prompt?" The AI will then list the specific context and details it requires, turning prompt engineering into a simple Q&A session.

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.

To get the best results from AI, treat it like a virtual assistant you can have a dialogue with. Instead of focusing on the perfect single prompt, provide rich context about your goals and then engage in a back-and-forth conversation. This collaborative approach yields more nuanced and useful outputs.

Instead of only giving instructions, ask ChatGPT to first ask you questions about your goal. This leverages the AI's knowledge of what information it needs to produce the best possible, most tailored output for your specific request.

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.