Cochlear implantation (CI) and cholesteatoma may be associated with a higher risk of disease recurrence and device malfunction, as widely reported in the literature. To reduce these risks, subtotal petrosectomy (SP) is the preferred approach, allowing radical disease removal and safe CI placement. As for simple chronic otitis media, CI can be performed in a single or staged procedure mainly based on surgeon’s perspective and philosophy; however, delayed implantation prolongs auditory rehabilitation. Intraoperative assessment often guides this decision. Key surgical principles of SP in cholestateoma and CI are shown, including en bloc matrix removal, aggressive drilling of bone in contact with cholesteatoma, and bipolar cauterization of soft tissue involvement.