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HeightsCast

Conversation: The Medium of Mentoring

The art of mentoring is not just for teachers and coaches, but also parents—who can never really be out of mentoring mode.

In a recent Substack article, Alvaro de Vicente named five pitfalls for our attempts at mentoring young men. This week, he talks us through some of the takeaways, reminding us that mentoring is not a profound lecture but an ongoing conversation, and the goal is not to modify but to form.

Chapters:

3:49 What mentoring is

4:35 Conversation as the basis

8:55 Parents: always in mentor mode

10:13 Presence over “meaningful content”

16:01 Weighty conversations

18:25 Daily conversations

21:24 Love unlocks a child

30:48 Urgent conversations

33:34 When to mandate

35:36 When to end the conversation

37:33 Formation is a game of inches

Links:

Men in the Making, Alvaro de Vicente’s Substack

Five Conversational Temptations Mentors and Parents Commonly Face by Alvaro de Vicente

Peace Like a River by Leif Enger

Only the Lover Sings by Josef Pieper

Also on the Forum:

Having Better Mentoring Conversations by Alvaro de Vicente

Forming Others: What Mentoring Can and Can’t Be featuring Colin Gleason

Anthropological Foundations of Mentoring featuring Dr. Joseph Lanzilotti

Mentoring without a Program: Joe Cardenas on Teaching the Whole Person featuring Joe Cardenas

Featured Opportunities:

Headmaster’s Lecture on Freedom in the Home at The Heights School (October 4, 2025)

Fall Open House at The Heights School (October 18, 2025)

Fathers’ Conference at The Heights School (November 1, 2025)

Convivium for Teaching Men at The Heights School (November 13-15, 2025)

About the Author

Alvaro de Vicente

Headmaster, The Heights School

In addition to his responsibilities as headmaster of The Heights, Alvaro acts as a mentor to high schoolers, and teaches senior Apologetics.

Learn More

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