Mentors have similar questions, especially during the first year. Should you have a question that's not answered here, or elsewhere on this website, contact Aimee Arens. See also Beyond the Basics and Worrisome Situations.
1. How do I know that I'm being effective?
Since every relationship is different, there's no definitive answer to this question. What's most important is to be friendly and supportive. Work towards becoming someone your student trusts enough to discuss topics that, for whatever reason, they don't wish to discuss with a parent, teacher, or counselor. Getting to this point requires both patience and time. You might find the document Building Relationships helpful (and reassuring).
While grades are certainly important, your student's grades are not a reflection of your effectiveness. As a mentor, you can encourage your student to have better organization and study skills, to attend extra study sessions, and to keep focused on their post-secondary aspirations. You can point them to any number of Academic Resources.
2. Who drives the relationship -- me or the student?
Mentoring is a dance where you take turns leading. As the grown-up, you will always lead when your student is making bad choices or isn't aware that the choices being made could be harmful. Your student may want to lead when you're deciding what's most important to be studying or choosing a special activity to do together. (However, students can be reluctant to suggest an activity. It's best to make a few suggestions as a starting point for discussion.)
Your student's parent may even want to lead. For example, the parent may ask you for help in some specific way. How you respond is up to you. You are not expected to get involved in family situations, nor are you prevented from doing so.
3. How can I help my student to be a better student?
Many teens lack good organization and study skills. Students have different learning styles and tolerances, so no one study method works for all. At a minimum, encourage your student to find a way to keep track of upcoming assignments. Missing assignments are endemic, it seems, and usually the cause of a lowered grade.
Remember that homework is often not the student's priority. Your text or phone reminders, and follow-ups, can help your student better track academic priorities and learn the importance of time management. These study tips might get you started finding what works best for your student.
4. How much do I push? Can I do anything that will be counterproductive or harmful?
Communication is the key to any successful relationship. By listening carefully, and responding to clues from your student, you will know when you've gone too far. But missteps can be overcome by being open and honest with your student, for example. "I feel I may be pushing you too much; I care about you and want you to reach your potential. What do you say we work together on this? If you think I'm overdoing it you need to let me, okay?"
5. What kind of relationship should I have with the parents/guardians? What if they're uncooperative?
Try to establish a relationship early on with your student's parents or guardians. Relationships between mentors and parents vary from pair to pair, and like all relationships, evolve with time and depend on the situation. Soon after you are paired with your student, reach out to the parents. Discuss how you'll communicate with each other. Check in with them as much as you feel is appropriate. Some families want to collaborate actively with mentors, other families are more circumspect, especially until you've earned their trust.
Unless you get clear signals to back off entirely, continue to make recommendations about your student to the family, but don't expect full cooperation from them in return. For example, you may encourage the family to create a study area separate from any household hubbub. Repeat recommendations as long as you feel they are essential for the success of your student.
Should the family not respond, look for ways to compensate for what's lacking at home. For example, if your student doesn't have a good study environment at home, encourage her to make use of the study tables at East, or to go to the public library together after school. Help your student to understand how effective study habits can lead directly to better grades.