Day 5: Surface hidden assumptions

Blind spots and rearview mirrors are how accidents happen, because you didn't see what was coming. The same thing applies to the future. Blind spots happen when experience turns into habit. Your past success quietly becomes an assumption, and so you miss or even dismiss key information because it just doesn't feel relevant. Now this is where AI helps, because it's not attached to your history, your incentives, or your comfort zones. So instead of asking AI to validate your thinking, which most of us do, use it to challenge it. Here's a few prompts to do just that. First, what assumptions am I making that feel reasonable to me, but would be risky to someone new making this decision? Second, if this decision failed six months from now, what would we say we underestimated? Third, what would someone who fundamentally disagrees with this strategy argue, and where might they be right? And fourth, what data or perspective would change my confidence level, and how likely am I to see it in…