Help! Should Students Be Allowed To DoorDash?

Dear We Are Teachers,

Help us break a tie. My lunch crew of fellow high school teachers is split. Half of us (me included) think students shouldn’t be able to use delivery services to the school for any reason. Our reasoning is singular: It overwhelms the front office staff. The other half of our teacher lunch crew says delivery services help kids who’ve forgotten their lunch or are ordering on behalf of a club or organization meeting. Who’s right?

—Debating delivery doubts

Dear D.D.D.,

Oh, I am firmly on the side that students shouldn’t be able to use delivery services at school.

It’s true that it creates a daily logistical nightmare for the front office staff. But that’s not my main opposition to it. The biggest reason I think it shouldn’t be allowed is safety.

When there’s a big crowd in and out of the main office, it would be very easy for an outsider to slip in.

Where there’s a chaotic and undersupervised exchange of goods, it would be very easy for someone to drop off weapons or drugs.

Also, now that delivery services can run errands anywhere, we’re opening up schools to receive special deliveries of things like booze. Fireworks. Live crickets. I don’t know … GLITTER.

Bear in mind that I’m imagining large schools because I’ve only worked at large schools. It might be different at a very small school. (But honestly, I still feel a little nervous about teenagers + underdeveloped frontal lobes + delivery of whatever they want.)

If students in a club or organization want a special lunch, their teacher can order it.

The end.

Dear We Are Teachers,

This coming school year will be my fourth year in the same district. And if everything continues as planned, it’s my fourth year split between two schools. I spend the morning at one school, then drive to the other halfway through the day and end there. I really love the teachers, students, and administration at both schools, I’m just tired of splitting and doubling. Splitting my time between two schools. Doubling the meetings, supplies, decorations, etc. Admin says there’s no full-time position. So do I double down and demand full-time, stay put, or start looking somewhere else?

—Should i stay or should i go

Dear S.I.S.O.S.I.G.,

I’ve been in this position! And weirdly, I believe it was also my fourth year in the district! Are we doing a matrix-y glitch thing here?

You’re right that it’s tough to split your time between schools. I know that was a rough year for me. Not in an extreme, panic-attack way, but just a quiet, sad way. In addition to your points, I also had a hard time not feeling like I belonged to either campus. At the end of the year, teachers in my hallway still looked at me puzzled, like, “Who are you again?”

Since I’m betting you have signed your contract for next year (and since it sounds like everything else about both schools has been lovely), I would have a conversation with your principal soon where you lay out the following:

  • Why splitting schools is so tough
  • What are some changes that can be made in the meantime (being paid for transportation between schools, seeing if you can opt out of certain meetings, etc.)
  • How much longer you’re willing to stay in this position

It might sound like this:

“I’m so grateful to be a part of [School 1] and [School 2]. I just want to be transparent about how tough it’s been for me to navigate splitting my time between schools. I stay on top of two schools’ emails, go to two schools’ meetings, and stay on top of paperwork, changes, and announcements for both schools. Plus, I have two classrooms to decorate, set up, prepare for testing, and take down. I know you don’t have a full-time position available right now and that’s out of your control. But I just wanted to be honest about my bandwidth out of respect to you and the staffing planning you have to do. I think I can stick out this arrangement for one more year. Can we discuss some changes that would make it easier for me in the meantime?”

That way, you’re making your needs known in a respectful way, but hopefully also lighting a fire under your principal to find a way to keep you in the next year. Plus, if they don’t try hard enough to keep you, you’ve set yourself up as a hardworking team player and clear communicator—qualities that will look great on a letter of recommendation for somewhere else.

Dear We Are Teachers,

I’ve recently accepted a new position as an Multilingual Learning Director. I’m so excited but also super nervous. It’s in a new district where I don’t know any of the teachers. Do you have any ideas/suggestions on how to build community, support the teachers, and help streamline communication? Basically, what’s the best advice you have on being a great leader?

—won’t settle for mid

Dear W.S.F.M.,

So exciting! Congratulations! We have plenty of resources about supporting teachers, building rapport, and just generally being the best leader around.

But before we get there, can I just give you a rundown of traits my all-time favorite school leaders have shared?

  1. They didn’t rush to conflict, but they also weren’t afraid it. I know it might sound weird to say that I valued a leader that isn’t afraid of conflict, but conflict is so necessary for any group to grow. I saw too often how our growth—as a school, a department, or a team—stalled when leaders refused to have tough conversations or negotiate conflict.
  2. They cared about me as a person, not just as an employee. They asked me about myself and the typical small-talk questions, but they also wanted to know about the way I think, how I make decisions, and my personality.
  3. They recognized my value. There’s nothing more demoralizing than busting your tail only to wonder, “Does anyone see this?” A kind email—even just two sentences!—recognizing achievements goes such a long way.
  4. They trusted me. I’m a naturally anxious person, so I’m already way more critical of myself than any leader has been. But I always did my best work with leaders who I knew trusted and believed in me.

Here are some more things to consider on leadership from our editorial staff and We Are Teachers community:

Congratulations! You’re going to do great.

Do you have a burning question? Email us at

Dear We Are Teachers,

The students at our high school drive so recklessly I constantly wonder when I or someone else are going to meet our demise on our way into the building. I’ve talked to my AP, but he just said that’s how kids drive. Is there anything that can be done to make things safer? 

—living on a prayer

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