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.
Virtual Grace Trail Experience
Bring the Five Questions to your people—wherever they are.
Designed for remote, hybrid, or distributed groups, Anne brings the Grace Trail experience directly to the screen through storytelling, guided reflection, movement, and conversation. Her warm, highly interactive style turns a collection of individual screens into a shared experience—drawing people in, lowering the pressure to participate, and opening the door to genuine conversation.
Ideal for: Groups of 10–100. Customizable for leadership, wellbeing, caregivers, veterans, students, and community groups.
Availability: Limited
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
Anne brings her signature warmth and the Five Questions to large stages and small groups alike.
Blending storytelling, live facilitation, and a guided Grace Trail walk turns a traditional keynote into something people actively experience together. Movement lowers the pressure, the Five Questions give conversation somewhere to go, and people leave having heard from one another—not only the person on stage.
Ideal for: Conferences, staff retreats, leadership gatherings, opening events, professional development, and community gatherings.
Availability: 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.
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
More Ways to Experience Grace Trail
Beyond virtual workshops and keynote experiences, the Five Questions can be brought into gatherings, programs, and communities in ways that fit the people and purpose at hand.
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.
Grace Trail has been adapted in partnership with organizations and communities for:
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Retreats
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Leadership workshops
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Team wellbeing programs
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Conference & convention pop-up trails
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Fundraising events
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Community gatherings
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Guide training
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Multi-site Grace Trail experiences
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Programs for veterans, caregivers, students, healthcare workers & leaders
Availability: Select engagements
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 or asked to share more than they choose.
Start Better Conversations
Gives conversations that may be difficult to begin a simple place to start—and space for people to listen to one another.
Connect Beyond Roles
Creates space to see the person beyond the title, age, role, background, or reason that brought them there.
Build a Shared Language
Five memorable questions create a common language people can use to genuinely check in, communicate, and support one another.
Move From Reflection to Action
Helps people consider what they’re navigating, recognize what they can influence, and identify a next step forward.
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
Turning Inspiration Into Action
At the Massachusetts Conference for Women, Grace Trail gives thousands of attendees a place to do something with everything they’ve just heard.
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.
