FAQs

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 Course, our most comprehensive support for the college-application writer. 

A student’s initiative, focus, perseverance, and writing ability are factors in how efficient the writing process is. At every stage, Hillside supports the writer’s positive 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 extend work with their coach through Feedback Sessions or E-Feedback.

Students should allow a minimum of six weeks to complete all the components of The Uncommon Essay Course, but the portion of the course that’s focused on live coaching can be completed in four weeks. The four meetings should be spaced at least a week apart.

The course includes our Discovery Process ahead of the first meeting (two weeks minimum), four private coaching sessions (two weeks minimum), and asynchronous Final Feedback (returned within one week of submission).

If you have any questions about setting up a schedule for your child, please contact us.

We recommend scheduling coaching sessions 7–10 days apart. This spacing is ideal, but sometimes scheduling considerations mean sessions will need to be further apart. When this is the case, it is especially important for students to attend to next writing steps promptly after sessions in order to maintain momentum.

We recommend the summer before senior year. Students can then turn their attention to supplement essays in the early fall. Students frequently begin The Uncommon Essay Course in June or early July and finish in August. Some of our coaches also offer spring availability, and some students opt to get started in May. This can work well for students who have busy fall schedules.

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 the 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.

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. (If you’re curious to learn more about how we use these responses, we recommend reading coach Eliza Turner’s blog post “The Value of Two Cents.”)

After the initial meeting of The Uncommon Essay Course, we produce a detailed Recap in audio-file, video, or written 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. 

No. We leave it to the writers to decide when and if they are ready to share essays with family members. This is deeply personal work, and student ownership is critical. See more in our Coaching Policies.

We believe strongly in the benefits of the Discovery Process that’s included in The Uncommon Essay Course, but we also understand that budget considerations or looming deadlines mean it may not be an option. We created Exploration Sessions for students who would benefit from a consultation with an experienced coach. Meetings can be held shortly after sign-up. Writers may opt to continue with their coach, who can recommend a support plan. Earlier in the coaching season, some students prefer to have an exploratory conversation before they begin The Uncommon Essay Course.

Since 2020, we have held all sessions remotely. We work with students who live all over the world.

You may request information at College-App Support Fees.

Learn about our cancellation policy and more at Coaching Policies. 

Yes! Learn about our support of the supplement essay-writer at The Supplements Launch.

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

Yes. Hillside coaches work with 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 and E-Feedback. 

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

All of our coaches have written posts for Hillside’s blog on college-app essay writing, sharing personal stories and craft lessons.