Trying to fill a hanging flower basket with holes to insert the plants
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It's best to do it from the inside before adding soil. Start at bottom, insert plants and then put just enough soil to hold plants. Then work your way up the flower basket. If you have a coconut type liner, you may need a knife to cut holes for plants.
Get a hole saw attachment for your drill, they come in many sizes from 1"-4" at the hardware store.
not sure if you are asking how to put holes in the pot or what to plant
I would just use a pencil. Stick the pencil in the hole, using the eraser side or blunt side and wiggle it around until the hole is big enough for you to put the plant in there.