Your Leadership Journey: A Retreat for Head Start Directors
October 27–29, 2026
Hilton Asheville Biltmore Park
Asheville, North Carolina
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.
Registration Deadline: October 16, 2026
Registration is limited to 25 participants and is available on a first registered, first confirmed basis.
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
✓ 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
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.
Hotel Information
Hilton Asheville Biltmore Park
43 Town Square Blvd
Asheville, North Carolina 28803
Group rate - $189.00 per night + applicable taxes
Hotel booking deadline - September 29, 2026
Hotel booking link - Hilton Asheville Biltmore Park Booking Link
Travel
All travel expenses, including lodging, transportation, parking, and other incidentals, are the responsibility of each participant or sponsoring program.
Please note: Participants are responsible for making their own hotel reservations through the room block. Reservations made after September 29 are subject to hotel availability and prevailing rates.
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