This is a common question of many mentors and one of the "beautiful challenges" of any mentorship. It's important to remember that in most cases, student's have a very limited social experience compared to ourselves. They haven't met or spoken to as many different people as you have or been in as many social situations and therefore may not fully understand how to be themselves, open and carefree. Considering this, here are a few tips for helping to understand your student and create avenues for better conversations.
1) Trust and time
Establishing trust with your mentee takes time. You can't say or do anything to speed this process up and it is very individualized. Meaning it depends on their personality. However, the more time you spend together on a consistent basis, the more comfortable and trusting they will be with what they tell you and how.
2) They may be shy
It's not easy putting yourself out there, especially when meeting someone for the first time. It can be easy to mistake shyness for disinterest. Keep the energy (and interest) up by asking about their interests, hobbies, or goals, and seeing if you can find common ground or something that piques their interest.
3) They're listening, even if it might not seem like it
It might feel disheartening to come see your mentee only to be met with silence, but don't take this to mean they are ignoring you. As mentors have found in the past, just because a mentee isn't talking, doesn't mean they aren't listening. Keep the atmosphere lively, and be ready for them to jump in when they are ready.
4) Distract each other with an activity
Whether you are using the Skills for Life packet distributed by HEF, reading the newspaper, coloring a book or playing checkers, activities will always help mentoring pairs "distract" each other into conversations. This can also break the monotony of conversations.
5) Ask the student to lead the meeting
At the end of the day, our mentorship is about helping the student develop personally and professionally. Taking ownership of their responsibilities in school is a great starting point. Ask you mentee to discuss what's on their "to do list" and encourage them to use your time together to either prepare for or participate in, accomplishing their required tasks (test preparation, selecting classes, organizing a student event etc.)