THE POWER OF THE QUESTIONS
The Five Questions of Grace Trail® are simple enough for anyone to answer and meaningful enough to revisit throughout life.
Through Anne's facilitation, participants experience the questions together, often discovering new insights, deeper understanding, and a shared framework they can continue using long after the experience ends.
Gain Perspective
People often discover answers they already have—but haven't had the space to hear.
Create Psychological Safety
The Five Questions create a simple structure that allows people to participate at their own comfort level.
Start Better Conversations
Simple questions create openings for discussions that often wouldn't happen otherwise.
Connect Beyond Roles
Shared reflection helps people see one another beyond titles, positions, and assumptions.
Build a Shared Language
Organizations, teams, and communities gain a framework they can return to long after the experience ends.
Move Forward with Intention
Participants leave with greater awareness of what matters, what needs attention, and what comes next.
Speaking Engagements
We live in a world that moves quickly. Reflection is often the first thing we lose.
Through the Five Questions of Grace Trail®, Anne Jolles helps audiences pause, gain perspective, and reconnect with what matters most. Her talks combine personal story, practical reflection, and audience participation to spark meaningful conversations that continue long after the event ends.
What makes the experience unique is its accessibility. The questions are simple enough for anyone to answer, yet powerful enough to uncover new insights, strengthen relationships, and create lasting impact.
Ideal for: Leadership events, conferences, healthcare organizations, educational institutions, nonprofit gatherings, and community events.
Availability: Select engagements
Virtual Grace Trail Experience
A shared Grace Trail experience—wherever your people are.
The Virtual Grace Trail Experience brings people together through a live, facilitated experience led by Anne Jolles. Participants move through the Five Questions of Grace Trail as a group, creating opportunities for reflection, perspective, and meaningful connection across locations.
Each experience is customized to the audience and can be adapted for leadership, wellbeing, caregivers, veterans, students, healthcare teams, community groups, and special events.
Ideal for: Remote & Hybrid Teams, Healthcare Organizations, Schools & Universities, Nonprofits, Community Groups, Conferences
Availability: Groups of 10–100, One planning call included, Limited availability
CUSTOM TRAIL EXPERIENCES
Support beyond the installation.
A Grace Trail is more than a physical installation. Anne helps bring the trail to life through guided walks, launch events, community gatherings, trainings, and special programs that introduce participants to the Five Questions and the shared language of Grace Trail.
Whether celebrating a new trail or creating new ways for people to engage with an existing one, each experience is tailored to the people, place, and purpose behind the trail.
Take a Digital Walk With Us
Experience the Five Questions of Grace Trail—anytime, anywhere.
Whether you're exploring Grace Trail for yourself or considering it for your organization, school, community, or team, the Digital Grace Trail offers a simple way to experience the questions firsthand.
Guided by an interactive experience created by founder Anne Jolles and powered by ChatGPT, you'll move through the Five Questions at your own pace in a private, judgment-free space that makes reflection simple, approachable, and accessible to anyone.
Just take a few minutes, slow down, and see where the questions lead.
Before You Begin: If you already have a ChatGPT account, clicking the link should take you directly to the experience.
If you encounter a message that says you don't have access, simply click "Retry" and follow any prompts that appear. Once the experience opens, type your responses where it says "Ask anything" and the Digital Grace Trail will guide you through the Five Questions one step at a time.
"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
Sustaining the Impact
A Grace Trail is designed to be used long after installation.
From trail launches and guide training to facilitator resources and community programming, Anne helps communities create meaningful ways for people to continue engaging with the Five Questions over time.
These offerings support local leadership, strengthen participation, and help the trail become an ongoing resource for reflection, connection, and wellbeing.
