Explain the assignment to the students. There should be some sort of rational for the drawing assignment. Perhaps they will be drawing implements used in cooking or items to be used as measurements for a science project. Maybe it is simply an exercise in drawing everyday things, but they will do a better job of creating the pictures if they have a framework for what they are doing.
Give the student a measuring cup, a No. 2 pencil and drawing paper. Let the student touch the cup, examine it, and finally draw it. Encourage students to add creative touches around the cup: a cake, a bag of flour, a science experiment, or some other idea of their own. Have them do some timed drawings or a drawing where they cannot lift the pencil from the paper.
Discuss fore-shortening and drawing cylinders. Demonstrate how our perception of a round surface will change depending upon how we are looking at it. Draw the cups looking up from underneath their location. Have the students sit on the floor and look up at the cup from that location, and draw the cup. Then ask the students to place the cup on the floor, and draw it while looking down on it.
Arrange the measuring cups as part of a still life. Place the still life in front of a white board or a piece of paper, and shine a strong light on it. Demonstrate how the still life, as a whole, has a consistent shape by drawing the outline of the shadow cast on the paper or board. Show how they can draw the various items in after they get the general shape of the composition as a whole.
Finally, give them the cups one last time. Ask them to draw the cup again.