||:Leaders Creating:||
5 min readMar 18, 2021



written by Gary Rupert, Leadership Coach & CulturE Strategist for ||:Leaders Creating:||

The band is marching back to the school from the practice field when you hear an obscenity laced tirade coming from the percussion section. You turn and realize the young man is screaming at the color guard adviser. Since this is a student who has been an ongoing problem, you go over to him and ask him for his drum. As he hands it to you, his best friend, also a drummer, tells you that you might as well take his as well. Two days later you find yourself in the Principal’s office for a meeting with the Assistant Superintendent. After explaining what happened, the Assistant Superintendent looks at you and says, “What would you say if I told you to reinstate the students back into the band.”

What will you do? Is this a hill worth dying on?

Well, this happened to me so let me tell you what I did. I paused for a few moments and then looked him in the eye and said, “If you are telling me I HAVE to do so, my resignation will be on your desk tomorrow.” When he asked me why, I told him that “there was no time in MY world where it would be acceptable for a student to treat a staff member that way.” He looked at me for a second and said, “Okay. I just wanted to know how strongly you felt about it.”

Was it a hill worth dying on? Yes!!!!

I was unwilling to abandon my core values for any reason.

As young educators you will invariably face challenges, hills which you must choose to climb or perhaps from which you need to walk away. I would like to tell you that your undergraduate school prepared you for this inevitability, but you will find out soon enough that they did not. In this article I will share some thoughts regarding where you can expect to find those hills and how you can determine whether they are worth dying on should you choose to defend. What you will not hear from me is which hills you should pick. You will have to make that choice on your own.

The phrase is a slight variant of “Is this the hill you want to die on?” which is often used in the military when discussing holding a position no matter the cost. When you decide to defend a position to the limit, then No better place to die” is often used. Both the Korean War and the War in Vietnam involved significant battles over hills that in some instances were taken at great cost, only to be abandoned shortly thereafter because they held little or no military significance. In hindsight, the cost of defending the hill was not equal to its military significance.

As band directors you can expect to confront challenges on multiple levels, few of which have any real significance to the delivery of instruction.

Student based — This is the area in which you will face the most hills. They are also the easiest to hold because by virtue of your position of power, you are already in control of the hill. While they may seem insignificant, over time, your position on these hills will have perhaps the greatest impact on your program direction and success.

Parent based — These hills are much rarer and are typically based on self-serving issues. (The parent feels their child has been slighted in some way and the only position of resolution they see is for you to give in to their wishes.) The most difficult thing about these hills is that not only are they challenging your decision or behavior, but it is likely they will contact your administrative superiors to challenge your power.

Community based — Perhaps the rarest hill you will confront but no less critical. Like the parental hill, these will be based on the needs/wants of the community and not necessarily of the program.

Administrative based — This is most challenging hill because in most cases, the Administration is in control of the hill; they are in the position of power. This is where major challenges like funding, scheduling, program direction, etc. are most likely to occur. The significance of these issues and the possible impact on your program are unquestionable and will undoubtedly arise at some point in your career. In my experience, these issues challenge the character and integrity of my program and were the hills in which I was willing to die.

This brings me to the all-important question:

The answer is…

When it is based on either your core values, or the core values of your program.

As an educator, you can afford to be flexible on the processes or procedures; the HOW. But you should never be willing to abandon your values; the WHY.

It concerns me that many teachers are unwilling to defend any hill because they are concerned about repercussions from the administration, complaints by parents, or even worse, finding their names in the paper the next day. They do not seem to understand that conflict is a good thing. It is about differing viewpoints. It is about the process of stating one’s position, negotiating for change, and compromise, all of which are designed to lead to a positive resolution. Conflict is not about who is right, but what is right. When we begin to see conflicts as zero-sum games, no one wins.

But just in case you are unable to come to a meaningful compromise or resolution, just remember there will always be hills to climb. And some are worth dying on. Only some!

EDITOR’S NOTE: We at ||:Leaders Creating:|| value the opportunity to engage with our readers, clients, colleagues, and friends. Please share your thoughts and questions in the comments section!

Gary L. Rupert was a music educator for 40 years and was most recently the Band Director at Smithsburg High School in Smithsburg, Maryland where his bands consistently achieved Superior ratings at local, state and national levels. He is a sought-after conductor and adjudicator in the areas of symphonic bands and jazz ensembles. An avid blogger whose daily entries are followed by people in over 57 countries, Mr. Rupert is the author of a daily inspirational book for students and teachers, “Today, No Every Day.” He is also a sought after speaker on leadership, motivation and creating a positive learning environment.

Gary Rupert has been named an Outstanding Maryland Music Educator, a Teacher of Excellence in both the Frederick and Washington County public schools, and has been twice nominated as a Disney Teacher of Excellence.

Gary can be reached at

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