I struggled with a title; the author IMO is a 'disruptive thinker', a theme that appears on SWJ in particular and using his own, long title would be wrong.

CWOT's interesting short article on this difficult topic, which often appears here and more widely in intelligence studies. It starts with a German (Prussian IIRC) quote pre-WW1:
In war you will generally find that the enemy has at any time three courses of action open to him. Of those three, he will invariably choose the fourth.

—Helmuth Von Moltke

With that quip, Von Moltke may have launched a spirited debate within his intelligence staff. The modern version of the debate can be said to exist in
the cottage industry that has been built on the examination and explanation of intelligence failures, surprises, omissions, and shortcomings.

The contributions of notable scholars to the discussion span multiple analytic generations, and each expresses points with equal measures of regret, fervor, and hope. Their diagnoses and their prescriptions are sadly similar, however, suggesting that the lessons of the past are lost on each succeeding generation of analysts and managers or that the processes and culture of intelligence analysis are incapable of evolution. It is with the same regret, fervor, and hope that we offer our own observations on avoiding intelligence omissions and surprise. Our intent is to explore the ingrained bias against outliers, the potential utility of outliers, and strategies for deliberately
considering them.
Link:https://www.cia.gov/library/center-f...iers-13Jan.pdf

CWOT cites several crowd sourcing surveys, which have appeared here and draws on those.