Attach a masonry drill bit to a drill.
Drill a hole through the entire wall. Make the hole a few inches above the bottom of the wall.
Insert a long stick into the weep hole to burrow a tunnel through the soil.
Repeat the process every 2 to 4 feet along the length of the wall. Keep the weep holes free from clogs by regularly inserting a long stick into the holes.
Dig several holes about 4 feet apart behind the retaining wall with a post hole digger. Make the holes as deep as the weep holes. Make at least as many post holes as there are weep holes.
Place filter fabric inside the holes you created with the post hole digger. Position the filter fabric so it lines the interior of each hole.
Fill the holes with washed stones that are about 3/4-inch in diameter. The filter fabric and washed stones will help drain the soil and help the water flow to the retaining wall weep holes.
Begin at one end of the retaining wall and apply a liquid membrane to the surface with a roller or trowel.
Spread the liquid membrane over the entire wall as evenly as possible.
Continue applying the waterproofing while working your way to the opposite end of the wall. Let the membrane cure for several hours. Wait to apply the waterproofing when there is no rain in the forecast.