Move Your Organization Forward with Intention
Interactive Keynotes, Virtual Workshops, and Custom Team On-Sites to build psychological safety and emotional resilience.
Virtual Grace Trail Experience
Designed for remote, hybrid, or distributed workforces. Anne hosts highly engaging digital workshops that bring the structure of the trail directly to your screen, establishing immediate team connection and reducing digital exhaustion.
Ideal for: Groups of 10–100, Can be customized for leadership, wellbeing, caregivers, veterans, students, or community reflection.
*One planning call required.
Limited availability
"Grace Trail doesn't tell people what to think or how to feel. It creates the space for them to hear their own answers — and find their footing."
— Anne Jolles
Keynote Speaking & Facilitated Walks with Anne Jolles
Anne brings her signature warmth and the 5-Question framework to large stages and small groups alike. Combining a live presentation with an immersive, guided walk, this experience is built for staff retreats, opening nights, and professional development days.
Availability: Select engagements
“Anne was our keynote speaker for a daylong professional development retreat for coaches and therapists. She combined sensitivity, compassion, professional coaching knowledge, and humor to create a dynamic and engaging learning experience for all attendees. I can’t say enough about the fabulous connection she made with our entire community.”
— Joan Schulman, Coach, Consultant, Facilitator
NorthEast Dare To Lead Facilitators Retreat /
Brené Brown Facilitators
Customized Grace Trail Experiences
Grace Trail can also be adapted for:
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Retreats
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Leadership workshops
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Team wellbeing programs
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Conference and convention pop-up trails
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Fundraising events
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Community healing experiences
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Guide training
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Multi-site Grace Trail experiences
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Special programs for veterans, caregivers, students, healthcare workers, and leaders
Availability: These offerings are currently considered on a selective basis and may require a planning team, approved Grace Trail materials, and a one-time event agreement or license.
Turning Inspiration Into Action
The Massachusetts Conference for Women continues to invite Grace Trail back because attendees value the opportunity to turn reflection into action.
Guided by Anne Jolles, participants are met with the warmth, curiosity, and thoughtful presence that have become hallmarks of the Grace Trail experience. Through the Five Questions, Anne creates space for meaningful reflection while helping attendees identify a next step they can take right away.
In a conference environment filled with inspiration, information, and ideas, Grace Trail offers something uniquely different: the opportunity to pause, engage, and begin. Rather than leaving with another insight to revisit someday, participants are invited to take their first step forward in the moment.
Not Sure Where to Begin?
Start with the Digital Grace Trail Walk or complete the inquiry form below.
"In just a few minutes, Anne created a cohesion in the group that hadn't been there before. She helped me broaden my thinking about my business and my life. Bright, effective, down to earth, and genuinely engaging, Anne was one of the most memorable parts of our three-day event."
— Szifra Burke
HOW THE FRAMEWORK SUPPORTS YOUR PEOPLE
The five questions are simple, but the space they create is intentional. Through Anne's facilitation, when an organization walks through them, it shifts the atmosphere and dynamics naturally.
Gain Perspective
Gives people a moment to clear the immediate noise so they can look at a problem objectively and find their own answers.
Create Psychological Safety
A predictable, low-stakes structure where individuals participate entirely at their own comfort level.
Start Better Conversations
Moves groups past superficial, routine updates and opens the door for genuine, helpful dialogue.
Connect Beyond Roles
Reminds people that behind the titles, departments, and daily emails, they are all human beings working toward the same goals.
Build a Shared Language
Provides a permanent, simple tool that staff can keep using to steady themselves long after the session ends.
Move Forward with Intention
Participants leave with clarity, a renewed sense of focus, and a practical next step they can take right away.
“Grace Trail is part of our culture. It helps keep our team above the line and able to work through even the most devastating circumstances. It keeps us focused on what we can do to help those we serve — instead of what’s out of our control.”
— Christine McSherry, CEO, Casimir LLC