Nice drawing
I'm used to Norwegian Pilot boats. Here we enter ships from the bow of the pilot boat, so the pilot have to walk around the superstructure to the bow area of the pilot boat. It is also safer to enter ships that way.
When a Pilot boat go up to a ship, the push starbord or port bow in to the side of the ship, to hold it in place, thus the aft of the ship would be pointing outward from the ship.
I have seen other ways to do it, but most of them aren't nice... to use if there is a little weather. But I presume you'r drawing is an harbor-pilot and not one that go out and meet ships, out there.
A Classic Norwegian one:
http://c8.alamy.com/comp/BP4W3G/pilot-v ... BP4W3G.jpg