I look for:
A basic understanding of how a boat
sails
A good knowledge of systems aboard -
bilge pumps, thru hulls,
engine start
All the required
safety items (PFDs, flares, sound making device,
navigation lights)
The ability to demonstrate tacking, jibing, heaving to, reefing, and other sailing skills
A good knowledge of rules of the road
Navigation skills - chartwork,
route planning, chart reading, tides, currents
Demonstrate good seamonship skills and decision making
Anchoring,
mooring, and
docking under a variety of conditions
Basic fire fighting skills
Basically everything you'd learn in sailing 101 andn 102.