I’m a newbie trying to learn how to DIY.

I’m trying to drill a small hole into the fiber cement siding on the outside to route wiring from the panel shown here to the garage right behind the wall. I wonder if I need to use stud finder or if I can drill anywhere I want. Is there anything else that I should pay attention before drilling?

Also, what kind of drill bit that I should use and do I need to use anything to cover the electric wire from snow/rain?

[![enter image description here][1]][1]


  [1]: https://i.sstatic.net/2fjRAcfM.jpg