danah boyd wrote an interesting op-ed for TIME called Let Kids Run Wild Online. She argues that restrictive monitoring software is not the way to go to keep teens safe online:

The key to helping youth navigate contemporary digital life isn’t more restrictions. It’s freedom plus communication. Famed urban theorist Jane Jacobs used to argue that the safest neighborhoods were those where communities collectively took interest in and paid attention to what happened on the streets. Safety didn’t come from surveillance cameras or keeping everyone indoors but from a collective willingness to watch out for one another and be present as people struggled. The same is true online.