Your Leadership Journey: A Retreat for New Head Start Directors

Please review the event details below before continuing to the registration form.

Registration Deadline: October 16, 2026

Registration is limited to 25 participants and is available on a first-registered, first-confirmed basis.

 

Your Leadership Journey is an extended leadership development experience designed to give new and emerging Head Start leaders time to learn, reflect, connect, and apply practical leadership strategies to the realities of their work.

Leading a Head Start program requires navigating many responsibilities at once—supporting people, strengthening systems, managing priorities, building relationships, making decisions, and ensuring the program continues moving forward. This experience creates intentional space away from the demands of the day-to-day work to focus on you as a leader—where you are today, what you are learning, and how you want to continue growing.

Through practical learning, meaningful conversation, reflection, peer connection, and real-world application, participants will explore leadership approaches and strategies they can take back to their programs and put into practice. The goal is not to provide all the answers, but to strengthen the knowledge, confidence, and leadership skills needed to navigate the role thoughtfully and effectively.
The experience begins with a three-day in-person retreat in Asheville and continues for four months through live virtual follow-up learning and individualized coaching—providing ongoing opportunities to apply what you learn, work through emerging challenges, and continue your leadership journey.

Is This Retreat Right for You?

Your Leadership Journey may be a great fit if you:

•   Are a new Head Start Director in your first 1–3 years and want to strengthen your leadership skills and confidence.

•   Are a manager or other aspiring leader preparing for increased leadership responsibility.

•   Want practical leadership development that goes beyond compliance and connects to the day-to-day realities of leading a Head Start program.

•   Value the opportunity to learn, reflect, and connect with a cohort of peers who understand the opportunities and challenges of Head Start leadership.

•   Want more than a one-time training and would benefit from continued learning and individualized coaching as you put what you learn into practice.

 

Your Registration Includes

✓   Three-day in-person leadership retreat, October 27–29, 2026

✓   Four 90-minute follow-up leadership webinars — one per month after the retreat

✓   Four one-hour individual coaching sessions — one per month after the retreat

✓   A copy of The Head Start Director’s Guide: A Practical Leadership Workbook & Journal for Your First Years, featuring real-world strategies, reflection tools, and Head Start leadership insights, plus access to the Director’s Suite, a collection of customizable tools and templates designed to support effective leadership and strong program systems. 

✓   Retreat materials and leadership tools

✓   Breakfast, lunch, and refreshments during the three retreat days

✓   Leadership Training Certificate of Completion documenting actual professional development hours completed, up to 30 hours

✓   Ongoing connection with a cohort of Head Start leaders

Hotel Information

Hilton Asheville Biltmore Park
43 Town Square Blvd, Asheville, NC 28803
828-209-2700
Group rate - $189.00 per night + applicable taxes
Hotel booking deadline – September 29, 2026

Please note: Participants are responsible for making their own hotel reservations through the room block. The link for the room block will be in the registration confirmation email. Reservations made after September 29 are subject to hotel availability and prevailing rates.

Travel
All travel expenses, including lodging, transportation, parking, and other incidentals, are the responsibility of each participant or sponsoring program.

Meals & Refreshments
Breakfast, lunch, and scheduled refreshments will be provided during each of the three retreat days. Dinner and meals outside the scheduled retreat program are not included. Participants will be asked to identify dietary needs during registration; every reasonable effort will be made to accommodate requests communicated in advance.

Follow-Up Learning & Coaching
The retreat is only the beginning. During the four months following Asheville, participants will reconnect for four live 90-minute webinars and four individual one-hour coaching sessions. The follow-up experience is designed to help participants apply what they learned, work through real leadership challenges, reflect on progress, and continue building confidence. Dates for the webinars and coaching scheduling information will be provided to registered participants.

Investment & Payment:

$3,700.00 per participant

Due at registration

Payment by credit card only.
 

The registration fee includes a $1,100 discount in professional services provided by Pinnacle Education & Leadership Partners that the program may consider as an in-kind contribution. Each registered participant is responsible for determining how the in-kind contribution may be documented and counted toward the program’s non-federal share. Pinnacle can provide supporting documentation of the discounted services.

Sample Three-Day Agenda

The agenda below is a general preview. Final topics, session sequence, and times may be adjusted to support the cohort and learning experience.

Daily meeting times: 8:30 am - 4:30 pm EST (local time)

Day 1 — Your Leadership Journey

• Welcome, connections, and retreat orientation
• The leadership guiding principles
• The unique role of the Head Start Director
• Understanding your leadership strengths and your own path
• Leading people while managing the work
• Listening, communication, and relationship-building

Day 2 — Leading the Program

• Understanding what makes Head Start Unique
• Seeing the Head Start program as an interconnected system
• Governance, partnerships, and the Director’s leadership role
• Using data, planning, and continuous improvement to guide decisions
• Priorities, competing demands, and critical thinking
• Leading through challenges and difficult situations

Day 3 — Moving Forward with Purpose

• Building systems that support people and performance
• Strengthening accountability, supervision, and team capacity
• Creating a personal leadership action plan
• Identifying resources, supports, and next steps
• Preparing for the four-month follow-up learning and coaching experience
• Closing reflection and commitment to action

Terms & Conditions

Payment. The full registration fee of $3,700 is due at the time of registration. Payment is accepted by credit card only. Registration is not confirmed until payment has been successfully processed.

Final payments / no refunds. All payments are final and non-refundable. Registrants are encouraged to confirm travel approval and availability before completing registration.

Participant substitutions. A sponsoring program may request to substitute another eligible participant from the same program before the retreat begins. Substitution requests must be submitted in writing to Pinnacle Education & Leadership Partners and are subject to approval and availability.

Emergency cancellation by participant. If a registered participant is unable to attend because of a documented emergency, the registration fee will remain non-refundable; however, Pinnacle may allow the participant or sponsoring program to transfer the paid registration amount to another eligible Pinnacle event occurring within 12 months of the original retreat date. The transfer must be requested in writing, is subject to space availability, and may be applied once. Any difference in registration fee for the future event will be the responsibility of the participant or sponsoring program.

Hotel and travel. Hotel reservations, transportation, parking, and all other travel expenses are the responsibility of the participant or sponsoring program. Hotel cancellation, early departure, no-show, and other lodging charges are governed by the hotel’s own policies and are separate from Pinnacle’s registration terms.

Event changes. Pinnacle Education & Leadership Partners reserves the right to make reasonable changes to the agenda, facilitators, session sequence, webinar dates, coaching schedule, or other program details when necessary while maintaining the overall purpose and value of the experience.

Cancellation or rescheduling by Pinnacle. If Pinnacle cancels the retreat and does not offer a rescheduled event, registration fees paid to Pinnacle will be refunded. Pinnacle is not responsible for airfare, lodging, transportation, or other travel costs incurred by participants. If the retreat is rescheduled, registered participants will be given the option to transfer their registration to the rescheduled date or another eligible Pinnacle event within 12 months.

Professional development hours. Professional development hours will be documented based on actual participation in eligible learning activities. Participants who complete the full experience may receive a Leadership Training Certificate of Completion documenting up to 30 professional development hours. The certificate is not represented as college credit or continuing education units (CEUs).

Conduct and participation. Participants are expected to engage respectfully and professionally and to maintain the confidentiality of personal or program-specific information shared by other participants during retreat, webinar, and coaching discussions.

Acceptance of terms. By completing registration and submitting payment, the participant and/or sponsoring program acknowledges and agrees to these registration terms and conditions.

Registration