In a pot, the water levels in the soil will always be un-equal - that's the nature of a pot. Its called a perched water table, in this case, the "perch" is the bottom of the pot. If you cut the bottom off the pot, the problem will go away but that's not practical if you want to grow a plant in a pot.
When you first put a plant into a pot, the rootball doesn't reach the bottom or sides of the pot. Do you know where most of the roots are now? If its a plant that appreciates moisture, probably in the bottom part of the pot. If its a plant that likes drier conditions, in the top part of the pot. The roots won't grow where conditions are uncomfortable. Knowing where the water levels are and what moisture level a plant needs are the only way to figure out when to water.
The pot in your photo is a fiber pot so the sides always be drier than the middle of the pot.
I hope this helps.