To do this, get a hose and run water into the well. The water should drain relatively fast and never come near the bottom of your window. If the water lingers, you will want to get this fixed as it just takes one major rainfall to cause basement flooding.
Clogged gravel: Gravel placed at the bottom of the well can get clogged with dirt, rotting leaves and debris over time, preventing water from passing through. You can easily fix this yourself by collecting the gravel and rinsing it off on your patio.
Loose window well: As the ground around your house freezes and thaws, the window well may shift away from your basement wall. A loose window well allows dirt to enter the well and block drainage. The loose-fitting window well needs to be dug out and properly re-attached to the house, so there is a tight fit against the wall.