Use AI to build a list of smart questions to ask before a decision, meeting, or commitment.

Before you agree to a project, commit to a timeline, or walk into a high-stakes conversation, you need to know what you don't know yet. The problem is, when you're rushed or caught off guard, it's hard to think of the right questions on the spot. AI can help you prepare by generating a list of clarifying questions tailored to your specific situation — so you show up ready to dig deeper, avoid assumptions, and make smarter decisions. 1. Describe the upcoming situation to ChatGPT: what you're preparing for, who's involved, and what decision or commitment is on the table. 2. Ask AI to generate 8–10 questions you should consider asking before you move forward — covering risks, timelines, responsibilities, resources, and expectations. 3. Review the list and pick 3–5 questions that feel most relevant or that you hadn't thought of yet. 4. Use those questions in the actual meeting, email, or conversation to gather the information you need before saying yes or making a call. This works for vendor pitches, project kickoffs, budget requests, role changes, new initiatives, or any moment where someone's asking you to commit before you've had time to think it through. You'll sound more thoughtful, avoid getting blindsided, and make better decisions because you asked the right things up front.

February 22, 2026