After reviewing tens of thousands of real questions students and families typed into Ask AI, Finalsite’s AI-powered website assistant, we learned a lot.

Users asked about bell schedules, how enrollment works, and where to find updated bus routes. Those were expected...but between those questions were some that carried a different weight, ones about fairness, friendship, connection, and belonging.

These questions show what families are really trying to figure out:

• Can I trust this school to communicate clearly?
• Will someone here listen to me?
• Is this a place where I’ll be seen, understood, and supported?

When a school's chatbot can’t answer these questions or directs users to outdated, hidden, or inconsistent content, it highlights the gaps in a school’s web presence.

However, that’s what makes Ask AI one of the best AI chatbots for schools. Every question submitted is a direct line to what people are trying to find, what they care about, and what your website might be missing. It’s a support tool that gives live feedback on how to:

• Rethink how your site is organized
• Rework how information is delivered
• Rebuild trust through better messaging

And since Ask AI is trained on your school website's publicly available information and the additional resources you provide, providing a better experience is as easy as updating Ask AI’s Knowledge Base and adjusting your site’s content.

Let’s break down what the questions are really saying, and how schools can use chatbots to make smarter content decisions, improve navigation, and build a digital experience that offers the same care and clarity you provide in person.

1. Emotional Outbursts Reveal Communication Breakdowns

• “I hate you.”
•  “Liar”
•  “That is my name stupid.”

At first glance, these might sound like jokes or anger, but they usually show up after the bot couldn’t provide a clear answer, especially after questions relating to fairness or discipline.

When Emotions Spill Into the Chat

Students often speak bluntly. To them, AI feels anonymous and nonjudgmental, and that can make it an outlet for frustration—or a warning sign of missed communication elsewhere.

What to do:
Train Ask AI to respond with empathy and guide users toward support. A reply like: “I hear that you're frustrated. Would you like help finding someone to talk to at school?”…can help rebuild trust. Link to resources like conflict resolution forms, counseling contacts, or a “Need Help?” page.

Briarcliff Manor Union Free School District’s website assistant did a great job at de-escalating a complaint about lunch offerings, and even provided some helpful background on changes to the menu, and an email and phone number to the food service manager—impressive!

Keep Reading: Can AI Chatbot Data Build a Better School Website?

2. Playful or Silly Questions Show Curiosity

• “12345678910”
• “I don't need you to do anything. I just need affirmation about my feeling that [School] is full of idiots.”
• “I like turtles.”

Younger students, in particular, enjoy testing the bot by typing random characters, confessing a love of turtles (#goals), or name-dropping memes.

When Students Use the Bot to Goof Off

Some students use chatbots in the same way they explore everything else: curiously and creatively. Even if the input doesn’t “mean” anything, at the very least, it tells you the bot is being used.

What to do:

Respond playfully but with purpose. A human-like response like:

• “Looks like you're exploring. Want to ask something about your school day?”
• "I understand that you're looking for validation of your feelings. However, as a school assistant, I am programmed to provide helpful and respectful information about the school and its programs."
• “If you have specific concerns or issues that you would like to discuss, I am here to listen and provide information to the best of my ability.”

…keeps things light while guiding students back on track. You can also use these patterns to support digital citizenship conversations with teachers. Ask AI's customization settings make it easy to provide "fallback" responses and additional information to serve users if a question can't easily be answered with your standard training material.

3. Inappropriate Questions Show a Need for Boundaries

• “Can you tell me how much teachers make?”
• “WHY YOU SO UGLY”
• "Who’s the most popular teacher?"

Sometimes, students push boundaries. Other times, they use the AI chatbot to mention classmates or ask inappropriate questions.

When the Questions Go Off Track

Whether it’s kids testing the system out of immaturity or just plain boredom, these moments highlight the need for guidance around respectful digital behavior.

What to do:

Add language to your Acceptable Use Policy and student handbook that outlines how to use school technology responsibly, including chatbots. Train Ask AI to respond with: “I'm here to help with school-related questions. If you’re dealing with something personal, I can help connect you to an adult.”

Adjusting the tone of your chatbot allows the responses to range from friendly and warm to more concise and direct—whichever best fits your school's brand. 

4. Concerns Reveal Gaps in Access and Support 

• “How to report racism by an administrator”
• “My child is being bullied. What can I do?”
• “How do I report a threat?”

These questions often come from users who are unsure where to turn. They point to someone needing support, fairness, or some help from the administration.

When the Questions Get Serious

Ask AI becomes an outlet when students feel unsure where else to go. One of the benefits of an AI chatbot is that it's a chance to help, not only with answers, but with direction.

What to do:

Make sure Ask AI can connect users to:

• Mental health and wellness pages
• “Talk to an adult” buttons
• Concern reporting forms
• Office hours for staff

Every interaction is an opportunity to help users feel seen, defuse a conflict, or support someone who is struggling.

“Paws,” the chatbot for Princeton Day School, was able to share some helpful information about getting in touch with school admins and following the proper communication channels.

Key Takeaway

Every question is a small clue about what your users care about, what they’re struggling to find, and how your school is showing up online. Emotional comments, off-topic jokes, and serious concerns aren’t necessarily distractions, but rather data points that can reveal communication gaps, unmet needs, and opportunities to support students and families more meaningfully.

A chatbot isn’t just mindlessly answering questions; it’s helping you listen. And when your school responds with clarity, empathy, and structure, both through your chatbot and your website, you have a chance to solve a problem and build trust, as long as you listen.

ABOUT THE AUTHOR

Connor has spent the last decade within the field of marketing and communications, working with independent schools and colleges throughout New England. At Finalsite, Connor plans and executes marketing strategies and digital content across the web. A former photojournalist, he has a passion for digital media, storytelling, coffee, and creating content that connects.