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.
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Instead of asking AI for answers, command it to ask you questions. Use the "Context, Role, Interview, Task" (CRIT) framework to turn AI into a thought partner. The "Interview" step, where AI probes for deeper context, is the key to generating non-obvious, high-value strategies.
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.
The most significant risk of AI is abdicating human judgment and becoming a mediocre content generator. Instead, view AI as a collaborative partner. Your role as the leader is to define the prompt, provide context, challenge biases, and apply discernment to the output, solidifying your own strategic value.
Go beyond using AI for data synthesis. Leverage it as a critical partner to stress-test your strategic opinions and assumptions. AI can challenge your thinking, identify conflicts in your data, and help you refine your point of view, ultimately hardening your final plan.
Log your major decisions and expected outcomes into an AI, but explicitly instruct it to challenge your thinking. Since most AIs are designed to be agreeable, you must prompt them to be critical. This practice helps you uncover flaws in your logic and improve your strategic choices.
Treat AI as a critique partner. After synthesizing research, explain your takeaways and then ask the AI to analyze the same raw data to report on patterns, themes, or conclusions you didn't mention. This is a powerful method for revealing analytical blind spots.
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.
AI models tend to be overly optimistic. To get a balanced market analysis, explicitly instruct AI research tools like Perplexity to act as a "devil's advocate." This helps uncover risks, challenge assumptions, and makes it easier for product managers to say "no" to weak ideas quickly.
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.
