Move Forward,
Together.
Experiences that bring people together—and give them something to carry forward.
A Shared Language
The Five Questions offer a simple, non-clinical way into conversations that aren’t always easy to begin—giving people space to check in, reflect honestly, and listen to one another.
Anne shapes each experience around the people and goals of the organization, helping teams build trust, strengthen connection, and develop a shared language they can return to long after the experience ends.
Laurie Dalton White
Founding Executive Director
Conferences for Women
Anne created a dynamic and engaging experience for all attendees. Her personal story and passion for Grace Trail set a tone of openness and curiosity. Working with Anne was a pure delight—she is responsive, reliable and “all in.” I can’t say enough about the fabulous connection she made with our entire community.
Kristen Alexander Lucas
Program Manager, Heroes In Transition
Anne has an incredible ability to create space for people to pause, reflect, shift their perspective, and recognize possibilities they may not have been able to see on their own. She has a rare gift for taking something that can feel complicated or overwhelming and turning it into a simple, accessible path toward change.
Virtual Grace Trail Experience
Bring the Five Questions to your people—wherever they are.
Step Out of Autopilot.
Five questions. Movement. Real conversation. Anne guides groups through a highly interactive experience designed to build connection, perspective, and forward momentum.
Ideal for: Groups of 10–100, including teams, leaders, caregivers, veterans, students, and community groups.
Limited availability.
Keynote Speaking & Facilitated Walks
Turn an audience into a connected community.
More Than a Keynote. Something People Experience Together.
Anne blends storytelling, live facilitation, and a guided Grace Trail walk to bring the Five Questions to life.
By moving beyond the stage and into shared reflection and conversation, audiences engage not only with Anne, but with one another—creating connection, perspective, and an experience they’ll remember.
Ideal for: Conferences, staff retreats, leadership gatherings, professional development, opening events, and community gatherings.
Select engagements.
Massachusetts Conference for Women, Boston MA
Anne Jolles has returned to the conference for multiple years as a speaker and facilitator, bringing the Grace Trail® experience to thousands of attendees.
Designed Around Your People, Purpose, & Place.
Grace Trail isn’t one-size-fits-all. The Five Questions can be thoughtfully adapted to your community, organization, or event.
UMass Boston Grace Trail®, Boston MA
Students walk the Five Questions with Anne Jolles, leaving their own reflections in chalk along the Trail as part of an interactive campus experience.
Additional Ways to Experience Grace Trail
Retreats • Leadership Workshops
• Team Wellbeing Programs
• Conference & Convention Pop-Up Trails
• Fundraising Events
• Community Gatherings • Guide Training
• Multi-Site Experiences
• Programs for Veterans, Caregivers, Students, Healthcare Workers & Leaders
Available for select partnerships and engagements.
Custom Licensed Grace Trail Installations
Transform your physical space into a permanent well-being destination.
Bring the Five Questions permanently into your campus, workplace, park, or community. We partner with you to design and license a Grace Trail thoughtfully integrated into your setting.
Unlike a one-time experience, a permanent Grace Trail becomes an ongoing, self-guided resource—inviting people to walk, reflect, connect, and return whenever they need it.
What We’ve Seen Along the Way
No two people experience Grace Trail in quite the same way. Still, over the years, certain patterns have surfaced again and again—in what people share, what organizations notice, and what they carry forward.
Create Psychological Safety
A predictable, low-pressure structure gives people a way to participate without being put on the spot.
Start Better Conversations
Gives conversations that may be difficult to begin a simple place to start.
Connect Beyond Roles
Creates space to see the person beyond the title, age, role, or background.
Build a Shared Language
Five memorable questions create a common language people can use to genuinely check in.
Move From Reflection to Action
Helps people consider what they’re navigating and identify a next step forward.
The Experience, In Their Words
Across organizations and communities, hear what people have discovered through the Five Questions.
“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
Grace Trail at the Massachusetts Conference for Women
Hear from an attendee about her experience.
“Staff are still talking about how she has helped them bring GRACE into their lives.”
After the presentation, I received an overwhelming response from the staff—texts, cards, and tokens of gratitude expressing how helpful and reassuring it was to listen to her speak.