May 26, 2026
Hi, friends, and welcome back to our series, “On Becoming: The Art and Craft of Personal Storytelling.” where we take a close look at personal essays written by real students, talking about why we love them, what makes them work, and how they came to be.
In this episode, I’m joined by Hillary Dickman, Senior Assistant Director of Admission at Colorado College. In past episodes, we've really broken down these essays and gotten into the nooks and crannies of what makes them work. But in this episode, I really wanted to get a sense of how Hillary sees essays from an admission reader's perspective.
We get into:
- What Hillary hopes to learn about a student when she sits down to read their essay
- What a great essay can do that the rest of the application can't
- How much essays matter and whether or not that's changed over the last few years.
- Why Colorado College does not have any AI reading essays or applications and doesn’t have plans to.
- She gives us an inside look at what it's like having your essay read in committee by as many as 13 people, and
- There's a moment in the episode where she imagines that I'm the co-reader reading the application with her and gives me the notes that she would give on the student if I was in the admission office with her.
I loved our conversation. I hope you enjoy it too.
Hillary Dickman is originally from the San Francisco Bay Area and holds a Bachelor’s and a Master’s degree in Speech Communication from Miami University in Oxford, Ohio. She began her career in higher education teaching at the University of Cincinnati and the University of Colorado at Colorado Springs. Since 2021, she’s been part of the admission team at Colorado College, and has also navigated the college admission process as a parent — her older daughter is a recent graduate of Wellesley College, and her younger one is a student at Colorado College.
Play-by-Play:
- 2:12 – What is often happening in admission offices during April and May?
- 3:14 – When Hillary reads a college essay, what is she hoping to learn about a student?
- 4:55 – What can a great essay do that the other parts of the application cannot?
- 6:05 – Hillary sets context for the essay and the student who wrote it.
- 7:35 – Hillary reads the essay, which we’re calling, “Where I Grew Up.”
- 11:59 – How does the author explore community building through this essay?
- 15:09 – What is the benefit to orienting the reader towards the topic early in the essay?
- 17:43 – Hillary describes the process of reading applications in teams and presenting files to a partner.
- 20:35 – Hillary breaks down how an admissions committee works.
- 24:15 – Hillary shares what makes it easy to advocate for a student and why real self-reflection stands out.
- 26:23 – Ethan and Hillary break down why a recurring theme and unique details can make your essay stand out when admissions officers are reading quickly.
- 31:12 – Why does Colorado College choose not to use AI systems to read student applications?
- 35:23 – How do small, specific memories keep an admissions officer engaged in your story?
- 40:06 – Does Hillary see the importance or role of the college essay changing in the future?
- 46:43 – What does Hillary love about her job?
- 49:12 – Closing thoughts
Resources:
- “Where I Grew Up” Essay
- State of College Admission - National Association for College Admission Counseling (NACAC)
- What do colleges look for in students?
- College Essay Guy’s Personal Statement Resources
- College Essay Guy’s College Application Hub