Help! My Most Challenging Student Is Also the Principal’s Child  

When I redirected him for his behavior with our guest speaker, he said, “What are you going to do, send me to my dad?”

Iillustration of a teacher whose most challenging student is also the principal's child (for Ask WeAreTeachers)

Dear WeAreTeachers,
I was honored when my principal said he picked me as his son’s 3rd grade teacher this year, but I’m struggling with his behavior and disrespect on a daily basis. He usually manages to toe the line just short of any office-referral-level offenses, but the last straw was when he asked inappropriate questions of our guest speaker. He told me, “What are you going to do, send me to my dad?” It feels really awkward to approach my boss with my concerns about the behavior of a child he raised. Any tips? —Biting the Feeding Hand

Dear B.T.F.H.,

Parent conferences have the potential to be awkward on their own. Adding in a tough social dynamic—like the parent being your boss—creates an entirely new level of cringe.

The best way out is the most direct. You’ll need to talk to your boss about his son’s behavior. Here are some tips on approaching tough conversations to soften the blow:

  • Use the “sandwich” method. Start with what you love about the student, then get into the area for improvement, and end on another positive note.
  • Approach him as a partner. Ask for his help, input, and insight so it feels like a partnership working toward a solution and not the delivery of bad news.
  • Set a time to follow up. Having a plan to reevaluate in the future helps not only with accountability on their end, but also helps to communicate your dedication to the process.

These might lead you to a conversation that starts this way:


“Thanks so much for meeting with me today. I wanted to start by saying what a great kid Noah is. He’s bright, driven, and knows how to influence his classmates. It’s that last part that I wanted to talk to you about. Sometimes I see that leadership play out in a way that keeps him from doing his best or that is disrespectful toward me or his peers. I would hate for any of that to limit his social or academic opportunities. Is this something you’re seeing at home?”

In other words, even though this feels like the pinnacle of awkward meetings, treat this like any other parent conference—with respect, professionalism, and kindness.

Dear WeAreTeachers,
We don’t have assigned parking at our school, but it’s an unspoken rule that the, ahem, more senior members of the faculty get the row of spots closer to the building. I’ve kindly told some of the newer teachers how it works and they act like they get it, but I still find their cars day after day in spots they haven’t earned. I know it’s silly, but it feels like they have a blatant disregard for a tradition that the rest of us have honored for decades. Do I talk to the teachers again or talk to my principal at this point? —Parking Police

Dear P.P.,

I know how I would respond, but I asked some of our readers to weigh in. Their responses covered some thoughtful angles I hadn’t considered. Check out what they had to say.

“As a more veteran teacher, I feel this one in my heart … but my advice is to let it go. We want new teachers to stay. We want them to love it here. Let’s just take a few extra steps for them and not make it a thing.”

“It creates such a divisive work environment when there are those unseen rules. Park based on the order you arrive, or let admin deal with it if they see it as a true issue (like an accessibility problem). Just because something is a tradition doesn’t make it a necessary system.”

“It might be worth a conversation with the principal about the rationale for not having assigned parking spots, and whether or not it might be easier for everyone if assigned spots were put into place. There are so many things that teachers have to worry and think about over the course of any given day. Taking one stressor out of the equation could be a huge relief and could eliminate potential divisiveness among staff.”

“Instead of keeping this tradition, why not start a new one? Being a new teacher today is harder than ever, and this seemingly harmless tradition could in fact make new teachers feel excluded. Perhaps a Teacher of the Month could be voted on by staff and students, and that teacher gets the best parking spot!”

Dear WeAreTeachers,
I teach high school biology, and I’m having a unique problem with one of my students. He’s great academically but has a habit of derailing class by bringing up wild conspiracy theories (think lizard people) during class. At first I thought he was being silly, but I really think he believes these stories. How do I get him to stop without distancing or insulting him? Do I focus on discrediting his theories or just that he’s causing a distraction? —Conspiracy Weary

Dear C.W.,

I’m smiling thinking about your tinfoil hat student. Curious, enthusiastic, bright, and bubbling over with wanting to set the record straight (even if his record is dead wrong). I came across this particular brand of student a lot in my work with G/T students.

Something to keep at the forefront of your mind when talking to this student is preserving the relationship. You don’t want to shame him, make him feel stupid, or kill his enthusiasm. Instead, connect, then redirect. Meet him where he is and help him see the value of pivoting that enthusiasm.

Sometime when you have him alone, say, “It can be really fun to think about conspiracy theories, huh? I love the idea of poking holes in something everyone else thinks is true, or exposing a truth no one else knows. Here’s the thing, though: Those kinds of discussions tend to get everyone sidetracked because they’re so exciting. It makes it hard for me to teach and for students to learn. Can you help me think of some solutions for what’s happening?”

Unless he brings up conspiracy theories that project harmful ideas about a particular group of people, I would focus more on the distraction part of what he’s doing than on discrediting him. He’ll figure it out eventually.

Do you have a burning question? Email us at

Dear WeAreTeachers,
Yesterday a student I don’t even teach rushed up behind me and pushed me. I fell and turned around to see a group of students filming me and laughing. Because the student says it was “just a TikTok dare,” this ninth grader is walking away with zero consequences. My AP said they already learned their lesson about peer pressure! I feel like quitting. Should I? —In a Shove-Hate Relationship