Like my colleagues across the globe, my daily battle revolves around how to make decisions through the lens of what is in the best interests of my students. This seems particularly trying in my current nontraditional school situation that is focused on dropout prevention, content mastery, and personalized learning—all still within the confines and with remnants of our traditional mindset. I often feel my opinion on what is in the “best interests” for our students can change several times within the same day.

Some of our most challenging decisions have the highest stakes for our students, including whether they are permitted to graduate. Students attend Sarah Pyle Academy (#SPAinspires) because they have realized they needed a different way to accomplish and access their education. There is no seat time, and students master their skills and content at their own pace. But I still can appreciate holding students accountable to deadlines and standards of behavior—we are, after all, preparing our students for life after graduation. Even so, I have a hard time not letting a student walk in their June or August graduation ceremony because they have missed a deadline for credit attainment if I know they can have their work completed and meet the standards in time to walk with their peers. Why should it matter when this learning occurs, then, as long as it is before graduation with time to practice?

Well, because in life there are deadlines. There are times when things need to be completed for work. There are times when you need to take medication. Often contracts include clear dates and times. This is the world in which we live. I clearly can see both sides.

I bring every decision back to our school vision— “together inspiring lifelong success through personalization”—and yet there is still no clear answer for each scenario. Especially on days when a student is in front of me and I have to deliver the message, “No, this is it. You did not meet your goals, and you are not eligible to walk in this graduation with your peers.” But I also add, “I will be here to support you so you will be ready to walk in our summer graduation when you have met all your goals.”

I have to hope that this is the motivation to not miss another deadline, and that this is the ultimate lesson learned and not the straw that breaks the proverbial camel’s back that will lead to the student giving up completely and never embracing the true value of all they are worth. Or do I let the student run the deadline to the next wire, extending it even further, hoping that this opportunity to finish gives them a “light bulb epiphany” to change patterns of behavior? Hoping this does not continue into an enabled pattern of learned helplessness. Hoping that this act of support is what they need to thrive and not just survive—that this is the individual personalization they need to reach their goal.

I try to look at each student as an individual, as I pray someone would with my own children if ever in this position. I evaluate if we made missteps along the way in supporting each student—if we could have done more—and weigh that into my decision. Some days I sway back and forth several times. It’s maddening. I wish I would just pick a side and stay on it, but it’s impossible because every situation is different, every student is unique, and every path has consequences.

Knowing my teachers trust that I have only our students’ best interests at heart makes it a little easier to wear the heavy crown of the final decision. They understand that I will listen to our students as well as teacher input, and although I may not agree, we all agree that we have positive intent and that no one has the right answer or a crystal ball.

Having a culture where it is okay to express vulnerability and uncertainty is the secret ingredient in making these conversations possible. One of my favorite movie sayings is “sometimes you win, sometimes you lose, and sometimes it rains.” I have my own adaptation of it—sometimes we provide just the right amount of opportunity for our students, sometimes we provide too many opportunities for our students, but we will never not provide enough opportunity for our students. That’s a chance I am not willing to take.

As we head into a brand new year, let us be clear of our expectations for all. Let’s revisit the intentional—and potentially unintentional—consequences of those expectations. Let’s take a hard look at all our policies and make sure that they reflect the values, learning, and lessons we want our students to come away with, not just what we have always done. Let us be mindful of always having our students’ best interests at the heart of every decision and build a culture where we trust each other along that journey.

How do you make the most difficult decisions? What are some of your policies around makeup work? Deadlines? Seat time and attendance? Do they align with the values of your mission and vision?

Kristina MacBury is principal at Sarah Pyle Academy in Wilmington, DE. She is an author, speaker, leadership coach, and advocate for school happiness agency. She is a 2018 NASSP Digital Principal of the Year and in 2017 was named a Top 30 Technologist, Transformer, and Trailblazer by the Center for Digital Education. Follow her on Twitter at @MacBuryKristina and visit her blog at

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