Familiarity is the enemy: On why Enterprise systems have failed for 60 years

Enterprise knowledge management systems have consistently failed to deliver value over 60 years because procurement decisions prioritize vendor familiarity and perceived safety over actual technological merit and business outcomes, resulting in an estimated $250+ billion in write-offs and opportunity costs. The structural problem lies in how organizations evaluate and select enterprise software—through analyst reports, RFPs, and established vendor relationships—rather than on solution effectiveness, perpetuating a cycle where innovative but unfamiliar vendors lose to risk-averse choices that fail to solve actual problems. As AI adoption accelerates, organizations risk repeating this costly pattern by defaulting to familiar vendors offering expensive transformation promises rather than identifying solutions that deliver superior results at lower cost.