Hi Mohit, in Ansys Workbench you need to create a manual contact region. Once you have done it, select a master surface (drill) and the slave surface, which in this case is the plate (the surface that is going to be penetrated). In WB master and slave surfaces are called contact and target, respectively. You also need to select the type of frictional contact -->Type-->Definition-->which in this case I suppose is frictional. The drill has to degress of freedom: displacement and rotation that need to be considered. There are other things that you need to consider such as the erosion of the elements where you can set up the level of deformation. Please let me know how you are doing that, I can try to help.

https://iopscience.iop.org/article/10.1088/1757-899X/1059/1/012020/meta