How to teach assertiveness?

Amor Chiquito has been interacting more and more with her cousin and our neighbors’ kids lately. I am noticing that she is very much a follower. This is disconcerting to me. I am not saying that I want her to be the leader. I feel that being assertive is vital, though. It is a very important skill that I want to help her develop. I want her to do the things she enjoys doing, to think about what it is that she likes or needs to do. I want her to feel comfortable speaking up when something makes her feel uncomfortable or sad.

Here is an example. Earlier today, Amor Chiquito was playing outside with the neighbors, ages five and two. Amor Chiquito does whatever the older girl does, which is pretty typical. At one point, the two-year-old began throwing sand at Amor Chiquito. There was sand on her face, near her eyes, in her hair... She did not say anything when it happened. Later on, Geeky Entrepreneur asked her if she liked that. She said “no.” He asked if it made her feel happy or sad. She said “sad.” We made a point of not showing any emotions or not asking questions in a suggestive manner. We wanted her to decide for herself how she felt about the sand situation.

Now what? We will tell her to tell us how she feels. Most importantly, we will make a point of using “I feel” statements. She will begin modeling eventually.

I feel that this is a good starting point, but that there is more to it than these ideas. If you have a little one, is s/he assertive? If not, what have you tried? How is it working out?

I look forward to your comments, thoughts and suggestions.