Yes

A sentence for the word pilot is " The pilot has to fly into Tokyo tonight."

You may split the wood if you don't drill a pilot hole first.

I can pilot your boat through these waters easily.

Most metals are initially drilled with a narrower drill, forming a pilot hole. Then the right size drill is used to complete the drilling of the hole by widening the pilot hole.

Start by drilling a round "pilot" hole, then shape it with an end mill.

That depends on the size of the finish hole. It should be big enough so that the larger bit will grab in the hole and not skate off.