The power of well-formed questions is amazing, isn't it? As you deliver a question, keep in mind the goal. Is the goal to have them answer it honestly; is the goal for them to answer the way YOU want them to; or is the goal to help THEM figure things out? Some questions from older admissions training methodologies used questions in a very manipulative way to get students to answer in a pre-determined way. Our challenge in today's environment is to reformulate questions to serve students in a very effective and ethical manner. The first question you have here is very good and begins with the word "How" which means they can't answer with a simple yes or no. This is a thought provoking question for them to determine how long they've been thinking of coming back to school. Perhaps it was just today or maybe they've been thinking about it for years. Either way, understanding their timeline is critical for both you and the prospective student. The second question can be defined as a "leading" question. With a little reformulating this question can be "tweaked" to help the student vs. telling them it is time to go back to school. How might you reword this question to increase effectiveness, Jose?