On Hillside's Practice

Nothing is more important than the working relationship we establish with a student — usually quite quickly — through asking questions, demonstrating genuine curiosity, and, in turn, drawing from the student motivating language.

Naturally, the success of the coaching plans we offer is dependent on a student's own initiative, focus, perseverance, and writing ability. The promise we make is that the attention we pay to every student’s story and efforts with language is professional and exceptional. Although it is essential that we work up-close to every student’s spoken and written words, an essay always remains a student’s own work; we keep the writer moving on the field while we coach from the sidelines.


Q:  How much coaching does a student usually need for the main application essay? What's the difference between The Uncommon Essay and The Jumpstart?

Every student and every student's essay-drafting is unique, of course, but Hillside's experience with a wide range of applicants has informed a main coaching structure of four intensive sessions that (1) are front-loaded by motivating and instructive "Discovery" steps; (2) incorporate discrete drafting deadlines; and (3) are followed by a coach's final online review of the essay. This is the design of The Uncommon Essay, our most comprehensive support for the college-application writer. 

We also offer The Jumpstart, which is specifically focused on beginning — on eliciting and exploring personal experiences and perspectives in order to find the most promising essay-writing material and to build a roadmap to Draft #1. Designed for students who do not need or want the rounds of drafting and feedback offered in The Uncommon Essay, The Jumpstart provides Hillside's Discovery steps and two sessions to establish the specific vision and plan for writing.

Naturally, whatever the support, a student's initiative, focus, perseverance, and writing ability is a central factor in how efficient the writing process is. At every stage, Hillside supports the writer's positive, energetic ownership of the project, which is key to achieving a memorable and authentic essay, and to achieving it with a sense of pride.

Students requiring support beyond the standard structures may elect to take advantage of Draft Feedback options. 

What is the Ten Sentences exercise? 

Hillside's Ten Sentences exercise is an efficient and motivating first step in a student's work toward a compelling application essay. It's both simple (not stressful!) and instructive. By guiding students at the outset to put aside given essay prompts and, instead, to gather an array of specific moments of experience in order to fuel conversation, the process invariably generates possibilities for authentic, meaningful writing. The yield of the exercise also becomes a valuable resource after a student has completed his or her main application essay and is turning to college-specific supplement essays. Every year, clients remark on the success of the exercise as a coaching method, and we receive requests from school counselors and educational consultants for instruction about it and the process it initiates.

What's the best role for parents in this process?

A positive and supportive role! Central to Hillside's approach to helping high school students applying to college is to take care of the writer. An anxious, pressured student doesn't think imaginatively or write easily, and she certainly doesn't enjoy the process. Getting to the stand-out essay requires patience and openness, and is best achieved in an atmosphere of curiosity and spirited discovery, the establishment of which is always Hillside's first goal.

Our most effective coaching includes communication with parents to encourage a supportive sideline team for a student, respecting the student's ownership of the project. All coaching sessions are with the student only. (For more on Hillside’s approach in this regard, we recommend reading Allan’s blog post “The One Who Knows.”)

Our "Two Cents from 'Rents" request, a preliminary step in essay-coaching, offers parents the opportunity to contribute memories, perspectives, and reflections to the discovery process for determining promising essay material.  

After the initial meetings of The Uncommon Essay and The Jumpstart courses, we produce a detailed Recap in audio-file or e-mail format that we send to the student and copy to parents. This personal review, which collects emergent ideas, underlines promising specifics discussed, and re-articulates the expectation for the next meeting, provides parents a clear sense of their child's direction, which can be helpful in conversations on the home front. As coaching continues, we remain readily available for questions and concerns from parents. 

Q: Where are essay-coaching sessions held?

Most essay-coaching takes place in Hillside's offices in Lexington, MA, though sessions are also conducted online using Zoom and shared documents. 

How much does essay-coaching cost?

You may request information about all coaching options and fees by sending us a message.

What is Hillside's cancellation policy?

Click Practices & Policies to read about Hillside's cancellation policy and more. 

Q: Does Hillside offer support to students writing college-specific supplement essays? 

Yes! Click here to learn about our support of the supplement essay-writer.

What about support for students writing essays other than the Common App essay and supplements?

We also work with students preparing transfer essays, honors- and scholarship-program essays, and writing for colleges that do not accept the Common Application. 

Q: Does Hillside work with students long-distance?

Yes. We work with students across the country using a combination of video-chat technology and online documents shared in "real-time." 

Q: What if I already have a draft written? Will Hillside review it for me and make recommendations for improvement? 

Yes. Hillside works with many students who have already completed essay drafts. We enjoy helping applicants advance toward the most compelling and memorable final draft. Read about The Draft Intensive, Draft Feedback Sessions, and E-Feedback here.

Q: Where have past Hillside clients gained admission? 

Students have gained acceptance to a wide range and very long list of competitive colleges and universities, including Harvard, Yale, Princeton, Brown, Dartmouth, Columbia, Tufts, Bowdoin, Bates, McGill, Claremont-McKenna, Cornell, Wellesley, Barnard, Vassar, UPenn, UChicago, UVM, Michigan, Tulane, Smith, Rice, Notre Dame ... and many, many others!

Q: What resources about writing application essays can you offer? 

Visit Resources for the College-Application Writer and also read posts related to writing for college that have been published on the Hillside blog, Sentence x Sentence.