“Brainstorming for that single supplement essay saved me many hours in the months to come. Almost every other college essay I wrote stemmed from the ideas we found."

—Cambridge, MA


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After completing the Common App essay, many students find themselves facing a challenging array of college-specific essay questions, each with a specified word limit.


For Example:

• What motivates you to learn?

Tell us about the place, or places, you call home.

You’re on a voyage in the thirteenth century, sailing across the tempestuous seas. What if, suddenly, you fell off the edge of the Earth?

Talk about a time, in or outside the classroom, when you worked with others and what you learned from the experience.

How have you been affected by a relationship you’ve had with someone who is very different from yourself?


And the most-common type of supplement prompt, which is some form of the following:

Why are you applying here?

Hillside enjoys helping students turn this challenge into meaningful opportunity. While presenting themselves as well-informed and genuinely interested applicants, students can provide new dimensions to their applications through thoughtful supplement essay-writing.


The Supplements Launch

Hillside’s strategic approach provides motivating and organized support for the project of brainstorming for and drafting supplement essays. The Launch is especially recommended for students who are addressing five or more substantial supplement prompts in addition to “Why are you applying here?” We recommend taking the Uncommon Essay course during the summer and scheduling The Supplements Launch for the fall. (Uncommon Essay clients get a boost in this project from the initial "Ten Sentences" exercise and all coaching exchanges that have followed from it.)

Here's how it works ...

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1. Collecting

The student completes Hillside’s "Why Apply Here?" Worksheet, which provides instruction for performing college-specific research. The Worksheet and a collection of the applicant’s supplement prompts, including word limits, are due to the Hillside coach at least 48 hours before the Strategy Session.

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2. Brainstorming

Coach and student identify promising areas of experience, isolating details and discovering efficiencies for addressing essay prompts. The coach also provides feedback on the student’s college-specific research. By session’s end, the student has direction and is ready to begin writing.


3. Planning

Following the Strategy Session, the coach creates The Supplements Planner — a customized, shared spreadsheet to help the student with project management. The Planner organizes prompts, word limits, deadlines, ideas, and session notes, supporting the strategic thinking necessary for efficient progress.


4. Revising

A close review of the student’s written progress (which must be submitted to the coach at least 24 hours before the session). As the conversation about revisions unfolds, coach and student update The Supplements Planner.


5. Refining

A second intensive draft-feedback session designed by the coach from study of the student’s submitted progress. The coach provides insight and instruction on tailoring revisions to address different supplement prompts.


Upon completion of the Launch, the student has a strategy and tools for completing the supplement project. If further guidance is desired, additional Draft Feedback sessions or E-Feedback support may be scheduled (depending on the coach’s availability).


Supplements Launch Sign-up & Scheduling

The Launch requires the scheduling of three one-hour sessions. The buttons below lead to coach calendars and to scheduling guidelines. Sessions can begin only after a student has completed work on his or her Common App essay. (As part of Launch Prep, the Hillside coach reviews the essay and all related Discovery material.)

NOTE: As a policy — one that supports the best writing and coaching experience — a student's Hillside coach remains the same from The Uncommon Essay Course or The Jumpstart Course through The Supplements Launch.