How Asking "Real Questions" Helps Me Help Teens

When I start working with a new student, the first thing we do is discuss some fairly logistical details. I tell them the best way to get in touch with me and where to find the shared documents we’ll use for their application process. And I explain to them that sometimes I’ll ask them a real question, and they can give me a real answer.

Communication isn't just the words you say

“Will you check your email once a day?”

“Do you think that writing exercise will work for you?”

“Can you have this done by Friday?”

Many students have picked up on the idea that the right answer to questions like these is yes, yes, and yes. 

And I’ve been part of many conversations where neurodivergent people lament the fact that, despite there being one correct answer, it’s still posed as a question. 

What if this student knows themselves well enough to know that they’re probably not going to check their email once a day? That the writing exercise suggested is going to end in tears and an incomplete assignment? In those cases, it would be much more direct and less confusing to skip the pleasantries and state the deadline.

I grew up in the part of New England where directness is considered rude. I’ve had the best antidote in the form of a few New York born-and-bred mentors in my early career, modelling clear but respectful communication, but at this point it’s been decades of trying to undo those conversational habits and I fear it’s just not going to shake. 

So instead of ordering students around (which doesn’t help my students with PDA at all), I ask the question that comes naturally, and I clarify that it’s a real question, as opposed to a leading one. I want them to give me the true answer, not the one that our counselor-student dynamic implies is correct. 

The first time someone asked me a real question

I didn’t come up with this on my own, of course. I remember very distinctly the first time an adult asked me a real question and paused to clarify what it was. In ninth grade, I was in a combined English-History class where one final project involved writing a sonnet about a historical event. Mrs. Wislocki, the English teacher, sat in a desk at a 90-degree angle to me, pointing to each line I’d written with her capped pen, reading it out loud. She got to the name of the river that the Taj Mahal is built on, the Yamuna River.

“Is that the right name?” 

I was kind of a smart-ass in high school. Okay, I was very much a smart-ass in high school. (Sorry, mom, and dad, and all of my teachers, especially Mrs. Wislocki!) I’m pretty sure I looked daggers at her before opening my mouth.

But she went on:

“That’s a real question. I don’t know the answer. I just want you to make sure you’ve got it right. If it’s right then I trust you.”

It shut me up and I’m pretty sure that’s when she changed from my least favorite teacher to my most favorite. (She deserved Most Favorite status, for sure.)

And – how many years later? I’d need a calculator to find out – I think about that interaction all the time and use it every time I meet with a student.

It makes both of our jobs so much easier.

Real questions pave the way for real connection... and real growth

As a real question, “Will you check your email once a day?” becomes an opportunity to talk about how to build email checking into their daily habits. We might take a few minutes to troubleshoot the default settings on the mail app that’s been slowing them down for the past couple of months. Instead of a scared “yes” and an unmet expectation later, we can proactively work to build a habit they’ll need to incorporate into their daily life.

As a real question, “Do you think this writing exercise will work for you?” becomes one of my favorite types of conversations: a dive into a student’s default writing process and what opportunities there might be to expand it. Instead of a nervous “yes” and a few hours of stewing about how to approach the exercise, the student has a chance to articulate the way their mind works (always helpful) and I can provide an alternative that gets them to the end goal more effectively.

As a real question, “Can you have this done by Friday?” becomes a practice opportunity for a crucial conversational skill: a respectful negotiation. Instead of probably just turning it in late, they get to step into the role of an adult with responsibilities and time constraints that matter just as much as anyone else’s, and we can talk through an alternative deadline that meets both our needs.

Real questions help me have realistic expectations for my students and their process.

And answering real questions gives my students an opportunity to self-advocate. Since that’s probably the most important skill they’ll need to develop as neurodivergent young adults navigating a system that isn’t built for them, it’s part of my job to help them get all the practice time they can.

Would real questions help your teen?

I still have room for some high school seniors this year, so I anticipate I’ll be explaining my real questions to more students soon enough. If you think my coaching style might help your teen or young adult tackle their college application process with less stress you can always send me an email or book a free initial consultation to learn more.

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