"Te estoy velando" is a common Puerto Rican kind of threatening expression used to let someone else know that you are keeping track and evaluating his/her actions. Because "velar" is what one does in a "velorio", if the person being watched wants to respond to the "velando threat", he or she will answer with a "yo no me he muerto para que me estén velando", or if he or she is a child... well you can imagine the consequences: "de pan y masa".
The elementary bilingual education classrooom, in the neighborhood bordering the Heights and Manhattan Valley, had a diverse student population. The Puerto Rican student-teacher being observed kept saying "te estoy velando" to a second grader that was not behaving very nicely, without getting any positive results from the kid.
So here you are, under supervision, the cooperating teacher and a college porofessor "velándote", and a kid is making life miserable. A child on automatic pilot, who, most probably, did not understand the very much culturally defined threat, can upset the most stable of us. The college supervisor knew that there was some type of cultural or generational miscommunication, and decided to intervene. He called the student teacher, smiled at her, in order not to scare her more than she already was and told her: "No creo que te está entendiendo, o no sabe qué es lo que està haciendo mal. Ve, sácalo aparte y dile lo que está haciendo mal y que no va a salir a jugar en el recreo, o cuslquier otro castigo por no hacer sus tareas". The student-teacher followed the instructions, and it worked. Kid stopped "la jodedera". Later on, this situation was used to discuss how cultures and diverse ways of evaluating influence how we teach and learn.
"Los estoy velando".