I have used these books as go-to resources as I work with middle school boys. I have personally read all of them and have found each to be helpful and encouraging. I may not necessarily agree with every part of every book, but would support the majority of content in all of them:
A Failure Of Nerve: Leadership in the Age of the Quick Fix
By Edwin H. Friedman
This book is not about parenting, nor is it about middle school students. However, it is probably the most influential book I’ve read in the past five years. It focuses on what you can do to be more active and effective in your relationships with other people. It affected how I interact with friends, family members, co-workers, and ministry students and parents, and I am confident it can positively impact how you approach parenting and leadership.
A Fine Young Man: What Parents, Mentors, and Educators Can Do to Shape Adolescent Boys into Exceptional Men
By Michael Gurian
Michael Gurian is a prolific writer about all things related to boys and their development. This particular book is chalk-full of information about adolescents boys and how adults can help them.
By Henry Cloud and John Townsend
This book is written to a general audience but has tons of practical applications for anyone who wants to have healthy day-to-day relationships with family members, students, and co-workers. Readers learn how to firmly love people without becoming enmeshed in unhealthy relational patterns. The authors have recently produced a number of spin-off books written specifically for parents, kids, and teenagers.
By Brene Brown
Brown is shame researcher who has recently gained national popularity for her work. This is one of the most influential books I’ve read in the past five years. It has a ton of applications to all areas of life but it has particular application to parenting. It challenges parents to do the hard work of focusing on who they are as a means of influencing their kids instead of just trying to change their kids.
Discipline That Connects With Your Child’s Heart
By Jim and Lynne Jackson
A highly practical book filled with real-life examples for how to discipline kids and strengthen your relationship at the same time. The authors write in a down-to-earth, easy-to-understand style.
By Donald Miller
Father Fiction is Donald Miller’s recollection of growing up without a consistent father figure in his life. It’s an enjoyable read because he approaches the topic in a way that communicates the serious need for dads, and yet he throws in a ton of humorous stories and insights. He sometimes borders on being cynical but then balances it with his brutal honesty and transparency. This book is especially helpful for understanding middle school boys who don’t live with their dad at home.
How to Talk So Kids Will Listen and Listen So Kids Will Talk
By Adele Faber and Elaine Mazlich
This book has had a huge impact on how I converse with teenage boys. It was written with parents of younger children in mind but still has a lot of transferable principles for those working with middle school boys.
Raising Cain: Protecting the Emotional Life of Boys
By Dan Kindlon and Michael Thompson
Raising Cain is the most impactful and memorable book I read during college. In it the authors argue that adults must help boys learn how to understand and articulate their feelings. This does not mean boys need to be “feminized.” Instead, the authors believe boys won’t develop into confident adult men nor fully embrace their masculinity until they become emotionally competent.
Sticky Faith: Everyday Ideas to Build Lasting Faith in Your Kids
By Kara Powell and Chap Clark
This is a landmark book filled with insights about how parents and youth workers can raise teenagers so their faith “sticks” with them after high school and into young adulthood.
Understanding Your Young Teen
By Mark Ostreicher (Marko)
This is an updated version of Wayne Rice’s Enjoy Your Middle Schooler. This book is written specifically to parents of middle schoolers. Marko is widely trusted and respected in the youth ministry world, plus he’s been a parent of middle schoolers himself. The book is realistic about the difficulties of raising middle schoolers but balances that with hope, encouragement, and practical wisdom.
The Wonder of Boys
By Michael Gurian
This is written by the same author as the first book on this list, but it has a more general approach to boys of all ages. I appreciate its emphasis on how boys develop most effectively when they are surrounded by a wide and varied constellation of other adults, mentors, coaches, teachers, and youth leaders, in addition to their own parents.