Clueless? That just means you're a beginner who's willing to learn. No need for apologies.
Yes, the moisture will, via capillary action, effect all the soil, including the surface. So always use that as the indicator as to whether or not the pot needs watering. If it's actually dry, it's time to water.
In fact, if the pot is standing in the water less than half an hour, and the surface becomes moist, you should pull it. You want the soil to have the consistency of a wrung-out sponge, not to be waterlogged.