Coaching Policies

Application Essay Coaching: Session Preparations & Deadlines

Good preparation and communication allows for good progress! Every Hillside essay-coaching session is customized through pre-session study of a student’s latest efforts. For the most effective support, students should therefore be prepared to respond promptly to all communications from their coach and to meet each deadline for sending progress. Not meeting deadlines or meeting deadlines but with insufficient or incomplete progress can make purchase of additional support necessary. The Hillside coach reserves the right to cancel a session if the student’s written progress is not received in time for the coach to prepare well for the session.

This is especially important for the Discovery steps that launch application-support programs, such as The Uncommon Essay Course and The WayFinder. For such programs, the parent input (“Two Cents from ‘Rents”), the student’s Ten Sentences Exercise, and the student’s response to coaching questions in the follow-up Ten Sentences Exchange all must be completed according to schedule. If Discovery is not complete in time for these support programs, or if a student’s Discovery materials are insufficient, Hillside may postpone launch — through cancellation of the first scheduled session — and require an additional session to be scheduled and purchased.

Hillside expects clients to acknowledge the limits to the amount of written material that can be effectively reviewed, discussed, and revised in a session meeting. Should a student send to a coach more material than the coach can review closely for pre-session planning — for example, in preparation for a Draft Feedback session or a Supplements Launch session — the coach reserves the right to ask for or to determine priorities with which to plan for the session time. Students who need a coach’s review of more essay drafts than can be covered in a session are advised to request additional support through E-Feedback. Hillside coaches are happy to work with clients to build strategic plans involving both real-time and asynchronous support.

Respecting Session Time and Environment

All Hillside coaching sessions are one-hour long, and we strive to make the most of every session. This goal naturally requires client cooperation. The Hillside coach reserves the right to cancel a session if the student arrives more than 15 minutes late to a scheduled session without prior notice, or arrives unprepared or in an environment inconducive to making progress. We require that students meet for their remote sessions with their Hillside coach while alone, in a quiet indoor setting, without distractions (including notifications from electronic devices). If a coach finds that the student’s environment during a session makes progress unduly difficult, the coach reserves the right to end the session and pursue a different mode of support or require the purchase of additional support in order to continue.

Extending Sessions

If a session is nearing its scheduled end just when breakthroughs are emerging or when momentum is high for addressing a particularly important stage in thinking, drafting, or revising, the coach and student may confer about extending the session to take advantage of the current environment for progress. If the student wishes to extend the session and the coach is able to accommodate, the coach will require parental permission for the extension and approval of its cost through text or phone call (unless prior arrangements for extensions have been made). Sessions may be extended in thirty-minute increments. Charges will appear in subsequent billing.

Student Ownership

Student ownership of the application-writing project is a critical part of our approach and philosophy. Protecting the writer’s space for authentic, individual discovery and reflection is essential to the writing process and to the personal education it provides. Except in special circumstances, all sessions are with the student only. The coach does not share a student’s material, drafting, or final essay with parents. We leave it to the writer to decide when and if they are ready to share essays with family members or with anyone else.

Coach Communication with Parent(s)

Student and parents are invited to meet the coach (via video call) and ask questions before the student begins The WayFinder or The Uncommon Essay Course. Parents are copied on the Findings and Recommendations (for The WayFinder) and the recap sent after Session 1 of The Uncommon Essay Course. The coach is also in touch with a progress report after the fourth session of The Uncommon Essay Course and before Final Feedback. If a parent wishes to talk to their child’s coach once the course is underway, the coach will offer a 15-minute phone call. If additional time is required beyond that call, parents may opt to schedule a 30-minute meeting with the coach for a fee of $75. For more on this topic, please visit our FAQs: What’s the best role for parents in this process?

Rescheduling Sessions

Hillside is as flexible as possible in accommodating clients who need to make changes to scheduled session times. During the very busy summer and fall seasons, however, options can be limited. The online scheduling system provides current availability, and the link for making changes is provided inside of confirmation e-mails to clients. The sooner we are aware of the need for a scheduling change, the better the chances we’ll be able to find a solution. If a client wishes to reschedule with less than 24-hour notice, or must be rescheduled owing to not having met a writing deadline, we reserve the right to charge the client for the cost of the session we’ve made preparations to hold. We also reserve the right to charge for rescheduling if a client’s repeated changes to session times have the effect of unfairly reducing a coach’s ability to be available to other students seeking support.


After a coaching session is scheduled and secured with deposit, we ask for at least a week’s notice for any cancellations. In the event of a cancellation with less than a week’s notice for any client who is not in The Uncommon Essay Course, we reserve the right to charge the session fee if we are not able to fill the session slot. Except in the case of emergency (health, family, etc.), the session fee is automatically charged for all cancellations with less than 24-hour notice. We can allow for one emergency cancellation per client.

Students signing up for The Uncommon Essay Course, The WayFinder, The Supplements Launch, Transfer Essay support, and Creative Mentoring (after the Introductory Session) are required to schedule more than one session. In fairness to others seeking session times, program reservations that remain incomplete in our system after five days are cancelled. We can hold complete reservations for seven days pending deposit payment.


Hillside does not require any payment up front for reserving session times online. After scheduling is complete, we review the reservation and then e-mail an invoice to clients for deposit payment, which can be made directly online via bank transfer, through Venmo, or by a personal check through the mail. Hillside does not accept credit cards.

Once a deposit is received, the coaching schedule is secured. Session times that have been scheduled but not secured through deposit may be made available to others after seven days.

For clients in The Uncommon Essay Course, The WayFinder, or other programs launched by Hillside’s Discovery steps, receipt of the deposit launches Discovery. Similarly, students signed up for Transfer Essay support will, after deposit, receive Hillside’s Five Questions, the first step in transfer-essay coaching. The Uncommon Essay, WayFinder, and Transfer Essay balance is requested — through an e-mailed link for payment — after the opening session and is due before the next session, or in the case of The WayFinder before the coach’s work begins on Findings & Recommendations. An automatic reminder is sent to clients about balances due. Hillside reserves the right to cancel scheduled sessions if balances remain unpaid past due dates.


The deposit for The Uncommon Essay Course, The WayFinder, and other support programs launched with Discovery steps is refundable — minus a $75 administrative fee — before a client receives access to Discovery materials. After Discovery launch and before the first session, 50% of the deposit is refundable. The Supplements Launch deposit is refundable (minus scheduling fee) if the Launch is cancelled two weeks or more before the Strategy Session (session #1); 50% of the deposit is refundable if cancellation occurs in the two weeks leading up to the Strategy Session. The Transfer Essay deposit is refundable (minus scheduling fee) if the support is cancelled a week or more before Session #1; 50% of the deposit is refundable if cancellation occurs in the week leading up to Session #1.

The deposit for Creative Mentoring cycles — 6 sessions per cycle — is not refundable. Deposits for individual Draft Feedback sessions, introductory Creative Mentoring sessions, The Draft Intensive, and Exploration Sessions are completely refundable if sessions are cancelled with at least a week’s notice and the Hillside coach has not yet engaged in any preparations for support.

[Updated 5.18.23]