As an introduction of the drilling symposium entitled “Lessons Learned from Cases of Success and Failure of Drilling Operations,” the author review the Risk Matrix and ALARP (as low as reasonably practical) principle which are today's de-facto standard risk assessment and risk management approaches, to effectively apply the lessons learned from cases of success and failure to the next drilling projects. In particular, actual applications of PDCA cycle in drilling project management are first reviewed, then examples of deficiencies of the risk matrix and pitfalls in risk assessment process pointed in some literatures are described. Recommendations for avoiding these failures in risk assessment and management process and for continuous improvements of drilling operations are finally summarized.