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

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

Also, do I need to use anything to cover the electric wire from snow/rain?

Thank you so much

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


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