As a system, the mining enterprise develops under constantly changing conditions of the external and internal environment. These conditions affect the state of the most important drilling subsystem: blasthole drilling technology, safety, performance, power consumption of the boring rigs and roller bits used. The main transition processes as necessary responses of the subsystem to changing conditions were identified as a result of fragmentary data analysis showing decisions taken over the past 15-20 years, which increase drilling activity efficiency and safety of smaller quarries of Russia, which contain a significant amount of material resources. The main transition processes contribute to the growth of drilling performance and consist of changing the following: bit design for specific rocks; drilling method; drilling mode; boring rig design; controlled parameters of drilling process and rock properties redetermination; parameters of maintenance and repair system. Based on the performed analysis, the systematization results of the main factors predetermining the need for transition processes implementation in the “drilling operations” subsystem were obtained and presented. The proposed approach allowed to reveal a holistic picture of the main interacting factors in the “drilling operations” subsystem. Based on the factors systematization presented in the article it is possible to envisage changes of individual factors depending on changes of other factors, not functionally related directly when planning drilling operations.