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Starting a Mentoring Program

The idea of starting a new program is exciting; the practical execution of the idea is difficult and takes time. This is especially true of a mentoring program. While the aspiration of truly personalizing the education at one’s school sounds good and beautiful, in truth, developing an organized program of formation that does more than merely sound good at an open house is perhaps one of the most difficult things to realize at a school. Nevertheless, with time and perseverance, developing an effective mentoring program is possible. 

The aim of this article is to assist school administrators who are serious about starting a mentoring program at their school. The article is not intended to offer a fool-proof, step-by-step guide to the perfect system. Any attempt to offer such a simple, out-of-the-box solution would betray the nature of such a personal enterprise. And plans and programs do not matter if the people involved are not committed and competent.

About Mentoring

Before discussing mentoring programs, a brief word about mentoring itself is necessary, as the term is used in a variety of circumstances to mean anything from a college counselor to a disciplinarian to a mental health specialist. For our purposes, mentoring can be defined as personal formation conducted on an individualized basis

Mentoring is a way by which a school assists parents in the formation of their child beyond a specific academic subject, extracurricular area of interest, or aspect of his life. It is the means by which a school’s overarching mission is made particular for each student. This understanding of mentoring distinguishes it from mental health counseling, college counseling, and other forms of advisory in so far as these activities are aimed at addressing a particular problem (e.g., anxiety) or advancing a specific goal (e.g., college admission) in a person’s life, and often require specialized professional training. Mentoring, on the other hand, is meant to be broader; it is, we could say, a tutorial in living well. More than the application of a specific expertise, mentoring implies the coordination of various parts into the bigger picture of a student’s life. Mentoring provides assistance to practical wisdom, the charioteer of virtues.

The Efficacy of Mentoring

The success of mentoring is difficult to judge. Unlike the work of a businessman or a medical doctor, whose success is more readably quantified, efficacy in mentoring is more difficult to judge with statistics. Because mentoring deals with human persons and because those human persons have freedom, there will never be a scientific, fool-proof formula for success. Any theory that pretends to offer something of this nature is fundamentally flawed. One’s approach to mentoring will always be based in anthropology, and an anthropology that denies human freedom will have disastrous consequences. Unlike, say, surgery, wherein the patient is acted on without his own engagement, in mentoring it is always the mentee who is the primary agent; the mentor accompanies. Presenting mentors with certain metrics as targets may provide a misleading goal for their work. The timeline for real success is quite long. It may take, for example, years of seemingly trivial conversations to prepare the soil for that one conversation that really helps a mentee, and the flowers of that conversation may only begin to bud several years later. 

There is data, nevertheless, that suggests mentoring to be an effective, perhaps the most effective, means of helping students. In a study of over 30,000 college graduates from across the United States, researchers from Gallup and Purdue University found that students who reported having a professor who cared about them personally—someone who was a mentor to them, whether formally or informally—were twice as likely to be engaged at work and three times more likely to be “thriving” in all areas of the “Gallup-Healthways Well-Being 5 View” (which includes well-being related to meaningful work, social life, financial success, community involvement, and physical health). While this particular study was limited to college graduates, there is good reason to believe the findings have bearing on primary and secondary school students as well. 

Personal experience may be a more powerful metric in seeing the efficacy of mentoring. Anyone who has had a good relationship with an older, more experienced person whom they trust and go to for guidance has encountered the power of mentoring. Moreover, there is no doubt that an experienced mentor at a school could share a plethora of stories about mentees expressing their gratitude for the impact the mentor had on his life.

Benefits of a Mentoring Program

Mentoring is important—potentially even the most important thing a school can do. Mentoring is likely necessary for a school that aims to educate the whole person to truly attain its end. Having a virtue talk every month or week is not enough. Teaching Aristotle’s Nicomachean Ethics is not enough. Despite its importance, mentoring is never urgent in the way that dealing with an immediate discipline issue or fixing a part of the building is urgent. Because mentoring has a long-term aim, it is easy for it to remain perpetually on the back-burner.

While teachers can and should mentor students informally, even outside of an official program, developing an organized program facilitates the actualization of the aspiration for mentoring to happen at one’s school. A program requires administrators to factor mentoring into how they organize their academic and extracurricular offerings, and it informs their approach to faculty hiring and development. For mentors themselves, planned meetings with mentees encourage them to be intentional and thoughtful about the way they mentor. The fact that a school designates a specific mentor for each student, moreover, communicates to students and parents that the school is interested in formation on a personal level. Thus, a mentoring program can serve as a helpful means to the personal formation of students.

Principles for Starting a Mentoring Program

  1. Involve parents. Parents need to be involved. They are the primary educators. Administrators may consider identifying families in their community who understand the mission and vision of their school well and engage them in the process of developing the program. It is no small thing for a parent to entrust their child to a school. Given the nature of mentoring, moreover, parents need to trust the school on an even deeper level for them to want the school to be involved in their child’s life in the way a mentor is. At The Heights, mentoring has been described as a conspiracy for the good of each student; trust is the foundation of this benevolent conspiracy.
  2. Take your time. The prospect of developing a mentoring program is exciting. But, if a school with a pre-existing culture and organizational set-up attempts to implement a program too quickly, it may fail. Just as mentors need to have a vision of the long-run when mentoring students, so too administrators need to think in terms of five or ten years when considering how best to develop a mentoring program for their school. 
  3. Communicate things to everyone involved. Before embarking on a journey, it is important to have the crew on board. For a mentoring program to be successful, support from the administration and the board is necessary. Because developing a mentoring program may involve adjustments to hiring, scheduling, and, in some cases, physical spaces in the school, not only the school head but his team and the board must all see mentoring as a core concern. Moreover, because mentors work closely with parents, a school ought to communicate its understanding of mentoring with parents. If parents and mentors are not on the same page, mentoring will likely fail. If a school is looking to start a mentoring program during the next academic year, for example, at the start of the current school year, the school head may consider communicating this idea with all relevant parties, eliciting feedback from them on the idea.  
  4. Have a clear mission and vision. Given that mentoring personalizes the education offered at a school, the precise contours that mentoring takes will differ according to the mission and vision of the school. For a mentoring program to be successful, parents and teachers must have a clear idea of the kind of man or woman they aim to form. What kind of man would the school hope each of its students to be at the age of twenty-five, fifty, seventy? Having such a vision will give mentors the proper orientation and framework for their work. Without a well thought-out and clearly articulated mission and vision, to allocate resources to establishing a mentoring program would be tantamount to launching a ship into the ocean without a clear destination.
  5. Consider your current faculty. Do I have a faculty that is missionally aligned? Are faculty open to doing this? At the beginning, it may work best for mentoring to be a voluntary, unpaid addition to teaching. As the program develops and the culture changes, schools can then consider adding mentoring to their teacher contracts. If none of a school’s current faculty seem able or willing, this will greatly inform a school head’s approach to hiring in the coming years.
  6. Consider time and space. Given the current course loads, do teachers have time in their day for mentoring? Can administrators open up time for this? Could mentoring a certain number of students be considered equivalent to a class? In the earlier stages of development, a school head may target a few teachers whom he has identified as showing potential to be good mentors, and lessen their teaching load to free them to take on more mentees. With time, a school administrator needs to think about the allocation of space. Does the school have appropriate places for meetings? Are they open enough while still allowing for a healthy level of privacy? For example, having windows in doors allows for transparency while respecting the private nature of many mentoring conversations. If there are currently no appropriate indoor spaces for mentoring in a school, perhaps a stroll around campus could be an option.
  7. Consider confidentiality. Where does it stop, where does it change? At times, students need a space to talk about difficult things away from their parents, but schools must be prudent in the way they go about this. Moreover, parents and students should be clearly informed about the scope of this confidentiality. It may be advisable for administrators to employ the assistance of a lawyer in developing guidelines concerning this matter. 
  8. Hire mentors, not just teachers. Hiring is the most important job of a school head. Developing a mentoring program ought to change how a school head looks at hiring. It is difficult, perhaps impossible, to quickly develop someone into a good mentor. Areas to consider when hiring are:
    • Faith and moral background 
    • Experience 
    • Disposition and ability to relate to students of a particular age
    • Desire to mentor
  9. Mentors should be mentees. A good mentor is someone who is himself seeking to grow personally and who, having lived longer and experienced real growth in his life, is thereby able to offer personal guidance to a mentee. While talks on mentoring are helpful, the most powerful way to help someone become a good mentor is for them to at the same time be a mentee—and this on two counts. In the first place, in addition to being good for someone personally, continuing to have a personal mentor of some sort (this could be a spiritual director, an older friend who takes you under his wing, etc.) has professional benefits for a mentor. In the second place, it is helpful to have a professional mentor (this person could be an administrator—a head of mentoring, for example—or more experienced mentor with the time to do so) who is able to offer one-on-one guidance on questions and difficulties pertaining to mentoring itself. Again, due to the intensely personal nature of mentoring, wholesale advice will never be as helpful as guidance tailored to each unique circumstance. Moreover, having someone to meet with on a regular basis will also fortify the mentor to persevere in accomplishing his work well when other areas of life and work make it tiresome to do so.


At a conference hosted at The Heights School a decade ago, Headmaster Alvaro de Vicente remarked that schools engage in the “art of imperfection.” More than a static building or a brochure of course offerings, a school is a dynamic collection of people—parents, teachers, students, administrators—all of whom are themselves works in progress. The work of a school, therefore, is always a work in progress. This is especially true of mentoring—truly personalized education—but it is a work well worth the effort.

About the Authors

Joe Cardenas

Head of Mentoring, The Heights School

Joe Cardenas is the Head of Mentoring at The Heights. Mr. Cardenas also teaches AP Art History, English Literature, and Freshman Theology.  Since coming to The Heights in 1994, he has organized cultural trips to Europe and service projects in South America. Mr. Cardenas completed his undergraduate work at the University of California, Berkeley, where he earned a degree in American history; he received his M.A. in Private School Management from Columbia University in Manhattan. He taught at The Head-Royce School, an independent school in California, and at inner-city programs in Chicago and the Bronx before joining The Heights faculty.

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Nate Gadiano

Executive Director

Nate is the Executive Director of The Heights Forum. In addition to his work at the Forum, he has also taught Natural History in the Lower School and Writing Workshop in the Middle School; he currently leads a philosophy seminar for high school seniors.

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