Me, I chisel three times, each in a different direction. Third time seems to do as much as the other two combined. Leave a little time between chiseling...letting the grass die and clods dry and break apart more easily....the timing and number of chiseling passes depends on the type of soil and grass you have. My dirt works best if the clods get a rain on them then dry out some between trips in the field.
Yes, the next step is your disk. Likely will need to also do this in two or more passes, at different angles, until the field is well worked up. Again, timing will depend on moisture content, grass clump size, etc....experience is your best teacher here. Angle of disks is also determined by experience. You want to be able to achieve a decent field speed which results in tossing the dirt up and onto the disks breaking up the clumps and knocking dirt away from roots. Maximum angle results in maximum dirt movement but also maximum drag...which your tractor may or may not be able to handle. Again, try several angles and speeds...observe the results and select what is working best for your dirt and size tractor.
Working up a field for the first time is kinda an art....you'll figure it out with some experience and get better each time.