On the basis of analysis of mining plans and field studies at mines of JSC SUEK-Kuzbass, it is shown that in conditions of increasing the size of excavation columns during the development of flat-lying coal seams the stress-strain state of the rock mass along the workings length changes significantly. The necessity of predicting the stress-strain state at the design stage of the workings timbering standards, as well as subsequent monitoring of the workings roof state and its changes in the mining operations using video endoscopes, is noted. The results of numerical studies of the stress-strain state of the rock mass during the development of excavation sites by three workings for various combinations of width of the pillars between the workings for mining-geological and mining-technical conditions of the “Taldinskaya-Zapadnaya-2” mine are provided. The stresses in the vicinity of the three workings are compared with the values obtained during the development of the excavation sites by double drift. A set of recommendations on the choice of the location of the workings, the width of pillars, timbering standards that ensure the stable condition of the workings throughout the entire service life at the minimal losses of coal in the pillars is presented.