Why do we keep asking the wrong questions in business? This episode dissects the dangerous habit of backward-looking thinking that’s plaguing professional discourse—from LinkedIn’s favorite “younger self” posts to the broader pattern of seeking control over unchangeable outcomes.Discover why the most popular business questions lead to the worst business thinking, and learn the framework for asking questions that actually drive results. We explore the psychology behind hindsight bias, the myth of shortcuts, and why your past mistakes were actually correct decisions.Key Topics:• The illusion of control in business decisions• Why hindsight bias makes you worse at current choices• The difference between productive and destructive questions• How backward thinking kills forward momentum• Better questions that force real insightFor business leaders who want to think more clearly and stop wasting time on intellectual comfort food.Iconoclast Insights challenges business orthodoxy and asks the uncomfortable questions that drive real results.

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