Managing Difficult Communication with AI Support

Scenario 1: Parent Email Overview:
You’re a college counselor at a high school that uses AI-assisted brainstorming to help students create balanced college lists. One of your students, a high-achieving junior with a 3.9 GPA and strong extracurriculars, met with you to begin list-building. After using an AI tool to co-generate a preliminary college list (based on interests, location, selectivity, and finances), the student brought the list home to share with his parents.

The next morning, you receive a sharply worded email from the parent. They are upset that the list includes schools they perceive to be “beneath” their son’s abilities and prestige expectations. They imply that you don’t understand their son’s caliber or goals and express disappointment in the counseling office's approach.

Your Challenge:
Using an AI tool (like ChatGPT), craft a professional, empathetic, and constructive response to the parent’s email.

Scenario 2: Student Email Overview:

Responding to Student Anxiety with Reassurance and Direction
Scenario Overview:
You receive an emotional email from a sophomore student who is overwhelmed after seeing social media posts about what “ideal” college applicants should be doing. The student is panicked that they’re not doing enough with their time — no leadership roles, no research, no standout “passion” — and worries they are already too far behind to be competitive in the college admissions process.

Their message is vulnerable, anxious, and full of fear about falling short. It’s clear they need both emotional reassurance and practical guidance.

Your Challenge:
Use an AI tool (like ChatGPT) to help draft a thoughtful response that validates the student’s emotions, provides realistic next steps, and reassures them that they are not “too late” to build a meaningful path forward.

Sample emails can be found here.

Use the AI tool of your choice to create several email drafts.

Experiment with Tone Variations – Try prompts like:

• “Write in a compassionate, calming tone.”

• “Write with a mix of empathy and action-oriented encouragement.”

• “Write like a wise mentor who’s been through this before.”

Compare and Discuss – Participants review multiple AI-generated drafts and discuss:

• How well did the tone match the student’s emotional needs?

• Did the response offer both comfort and clarity?

• What would you add or change before sending it?

Debrief Questions:

• How can tone be a tool for de-escalating anxiety?

• What role can AI play in helping you think through tough emotional conversations more intentionally?

• How can you use AI to practice your counseling voice, not replace it?