September 16, 2026 - October 14, 2026
OVERVIEW
A five-week virtual leadership experience for leaders ready to trade AI ambivalence for AI agency.
AI is everywhere, and it is easy to feel like you are already behind. You suspect it could make your work lighter, but you cannot find the time to learn it. Underneath the time problem, there is often a quieter hesitation: a nervousness about handing your thinking to a machine, real questions about ethics and impact, and a sense of being stuck in your own ambivalence.
This five-week Circle, co-led with Stephanie Colores of Strategic Connexus, helps you:
Build the skills: Develop the leadership capabilities that let you work with AI on purpose, not by accident.
Excavate the barriers: Name and work through the real barriers, practical and ethical, that keep you stuck in ambivalence.
Practice on a project: Choose a single project from your day-to-day work and integrate AI into it, with live support along the way.
You will leave having grown your capacity immediately, with a responsible, clear-eyed approach to AI and a roadmap for where to use it next.
Join us to trade AI ambivalence for AI agency, because the judgment, the hard calls, and the responsibility still belong to you.
Who Should Join
This Circle is best for values-driven leaders, founders, consultants, managers, and professionals who know AI matters but want to approach it with discernment, responsibility, and practical clarity.
This experience is especially useful for those who:
- Feel behind, hesitant, or overwhelmed by AI
- Want to use AI without outsourcing their judgment
- Have ethical questions about how AI should and should not be used
- Want live support applying AI to real work
- Are ready to build practical skill without losing the human center of their leadership
What’s Included
The Leading with AI Circle includes five live virtual sessions on Zoom.
Dates:
Wednesdays from September 16, 2026 through October 14, 2026
Format:
Live virtual sessions via Zoom
Commitment
Each session builds on the last, creating a layered and meaningful experience. Participants are encouraged to attend the full Circle to receive the greatest value and contribute to the shared learning of the group.
Pricing
Sponsor: $500
Support another leader while deepening your own leadership experience.
Supporter: $450
An intentional investment in your own leadership growth.
Rising Star: $400
A supported rate for leaders who could use a little boost.
About “Lead Like it Matters”
Lead Like It Matters is a series of leadership development programs for thoughtful, values-driven leaders navigating growth, change, pressure, and uncertainty. Through immersive leadership retreats, Wisdom Circles, workshops, coaching, and community, leaders strengthen the clarity, steadiness, self-awareness, and courage required to lead well.
This is not traditional management training. It is a space to step outside the pace of daily work, examine the patterns shaping how you lead, and reconnect with what matters most. Each experience combines guided reflection, meaningful dialogue, practical leadership tools, and the wisdom already present within the room.
Designed for executives, founders, managers, and emerging leaders, Lead Like It Matters helps you build trust, navigate conflict, practice accountability, make aligned decisions, and lead through complexity without losing yourself in the process.
September 16, 2026 - October 14, 2026
