For Leaders Making the Decisions That Matter Most
Helping high-achieving leaders and organizations build sustainable success through values-based leadership.
Annie Stephanos,
founder & operator
Meet Annie
I'm Annie Stephanos, founder of Highroads Coaching.
After 26 years as a teacher, instructional coach, and leadership coach in public education, I came to understand something that changed the way I think about leadership.
Burnout rarely begins with one big decision.
It grows through hundreds of small ones—often made with the best intentions—that gradually pull us away from what matters most.
That realization became the foundation of the Highroads Decision Process™, a practical framework that helps leaders make values-based decisions with greater clarity, confidence, and sustainability.
Today I work with leaders, teams, and organizations who want to build success they can actually sustain.
My Approach
• Values before velocity.
• Practical, structured, and evidence-informed.
• Focused on better decisions—not just better coping.
• Designed for sustainable leadership.
Shelby Garay
Program Director, Headspace Training Institute
“
Annie has led several workshops for the Headspace Training Institute on the topics of Know Your Worth: Eliminate Burnout for Good and Step by Step – Building Your New Coaching Business, which were extremely successful. She brings a rare combination of deep expertise, clarity, and genuine care to her training. Annie creates an engaging, supportive environment while delivering practical, actionable insights you can immediately apply. Her ability to explain complex concepts in clear ways makes her workshops both engaging and empowering. If you’re looking for a knowledgeable, impactful facilitator who helps people move forward with confidence and purpose, Annie delivers this and more.
Mary Alice Keator
Program Approval / Continuing Education Manager, National Board for Health and Wellness Coaching
“
Annie has a unique ability to meet people with compassion while still challenging them to grow. Her work is grounded in real-life experience and a genuine understanding of what it means to navigate burnout, rebuild balance, and create meaningful change. She doesn’t just teach concepts, she helps people integrate them in a way that feels sustainable and empowering. As reflected in her work, Annie is deeply committed to helping individuals reconnect with themselves, set boundaries, and build lives rooted in well-being and purpose.
Make values-based decisions with greater clarity.
Lead with confidence instead of constant pressure.
Navigate difficult decisions without losing themselves.
Build sustainable success that aligns with what matters most.
Strengthen leadership from the inside out.
It all starts with the Highroads Decision Process™.
Services & Pricing
Work with Annie
A Note for Non-Profit Organizations
I believe deeply in supporting mission-driven work. A limited number of reduced-rate engagements are available each year for non-profit organizations aligned with this mission.
Foundational Keynote
Shift the conversation. Spark awareness.
A powerful, thought-provoking keynote designed to reframe how high performers think about success, energy, and burnout.
45–60 minute keynote
Audience engagement
Signature Highroads concepts
Optional Q&A
Founding Investment:
$2,000 - $4,000
Non-Profit Investment:
$1,500 – $3,000
Best for:
Conferences, company-wide events, leadership summits
Interactive Workshop
Move from insight to action.
A dynamic session where participants begin applying the Highroads Framework™ in real time—building awareness, clarity, and immediate behavioral shifts.
60–90 minute workshop
Guided reflection
Customized to your audience
Practical tools
Founding Investment:
$3,500 – $7,000
Non-Profit Investment:
$2,000 – $4,500
Best for:
Teams, departments, emerging leaders
Private Coaching
Move from pressure to grounded, sustainable success.
A personalized coaching experience for high-performing women ready to stop operating from urgency, rebuild self-trust, and lead with clarity, calm authority, and disciplined energy.
60-minute private coaching sessions
Highroads Framework™ in action
Customized to your goals and season
Guided reflection and practical tools
Per Session:
$300
6 session Package:
$1,650
12 Session Package:
$3,000
Best for:
Professional women, leaders, business owners, educators, and high performers
Signature Highroads Experience
Create lasting transformation.
A deeper, immersive experience designed for organizations ready to address burnout at the root and build sustainable performance systems.
90–120 minute or half-day experience
Live coaching & strategic application
Highroads Framework™
Pre-session alignment
Founding Investment:
$7,500 – $12,000
Non-Profit Investment:
$4,000 – $8,000
Best for:
High-performing teams, leadership groups, culture initiatives
Corporate Partnership
Embed sustainable success into your culture.
Ongoing strategic partnership to support leaders and teams in building long-term resilience, clarity, and high performance without burnout.
Ongoing sessions (monthly or quarterly)
Leadership support
Mix of workshops, coaching, and advisory
Burnout prevention strategy
Founding Investment:
$15,000 – $35,000
Non-Profit Investment:
Custom, based on scope
Best for:
Organizations committed to long-term cultural change