Prepare a space for each child:
A placemat with a pitcher filled half way with water
2 Smaller cups
Have washcloths nearby to offer when they have larger spills.
When your child is interested, invite them to practice pouring. I demonstrated pouring from the pitcher into one of the cups once for them. Returned the water back to the pitcher and then turned it over to them.
Allow them to practice freely. Spills will occur. For larger spills, ask them to help you wipe it up and then see if they would like to try again with more water.
Liquid Measuring Cup for Pouring (we call it a "pitcher")
Smaller clear cups (I used small Tupperware and recycled fruit cups)
Washcloths or Towels
-Offer the same pitcher with water for them to pour into their cups at a meal time
-Move on to milk when they are getting more confident and accurate