What Matters Most
A Leadership Retreat on Clarity, Choices & Priorities
Pause, Reflect , Clarify Priorities, Move Forward
Five days dedicated to your personal and professional growth. We build a space to examine the challenges you face, clarify the goals that matter, and identify practical steps toward realizing them in your life, your leadership, and your business.
Through Solution Focused coaching, guided reflection, and meaningful exchanges with a small circle of leaders, you will work on the priorities you bring, explore different perspectives, and develop clearer intentions for the decisions and actions ahead.
Tuscany provides the setting and the space for this work. Walking, shared meals, and time away from everyday demands create opportunities for focused reflection and open exchange, helping you return with a clearer sense of direction and practical commitments to carry into your life and leadership.
Why Five Days?
For a senior leader, five days away from work is a meaningful commitment. Responsibilities continue, decisions still need to be made, and there is rarely a convenient time to become less available. Yet those same demands are what make sustained time away so valuable.
The questions that shape how you lead cannot always be answered between meetings, messages and competing priorities.
A single workshop can introduce an idea. Five days create the time to arrive fully, clear the noise, explore beneath the first answers, see familiar challenges differently, and decide what deserves to change. The retreat is not time taken away from leadership. It is time invested in how you return to it.
Participants will not be expected to become unreachable. Reasonable access can be maintained for genuinely important matters, while the retreat protects substantial periods from the interruptions that normally make deeper thought so difficult.
Coaching Throughout the Journey
Throughout the five days, Stefano leads outdoor Solution Focused coaching centered on the priorities each participant brings to Tuscany. Each leader has opportunities for focused one-to-one coaching while the rest of the group observes, followed by reflection on what participants noticed, experienced and learned, without advice or judgment. These coaching encounters unfold throughout the journey..
DAY ONE
A half-day guest session with internationally respected coach Charlie Davies, originator of the Language of Commitments, who joins remotely. Building on themes that emerge from the cohort before Tuscany, Charlie guides the group through a shared question connected to clarity, choices and what matters most.
Stefano then leads an outdoor group coaching encounter near Siena, helping participants reflect on what has emerged, connect those insights to their own leadership challenges, and bring their personal and professional priorities into sharper focus.
DAY TWO
A half-day embodied session with Dr. Christoph Helferich, a psychotherapist specialized in Bioenergetic Analysis and body-oriented practice, who joins the group in person from Florence. Accessible movement, breathing and postural awareness help participants step out of the pace of executive life, allowing the body to catch up with the mind and bringing their attention fully back to the present.
Later, a guided walk through the Tuscan countryside leads to Monteriggioni, the ancient walled town overlooking the surrounding hills. Walking side by side creates space for open, unhurried exchange and deeper connection among participants.
The day closes over an informal dinner together, with time to reflect on the day’s encounters and insights.
DAY THREE
The morning centers on an outdoor Solution Focused coaching encounter, creating space for participants to move beyond their first answers, explore their personal and professional priorities, and learn from the perspectives and experiences of the group.
In the afternoon, the pace shifts at Le Caldane, natural springs known since Etruscan and Roman times. Time by the water offers space to rest, exchange reflections, and consider how the morning’s insights relate to the challenges and goals each participant brings.
The day closes in the medieval upper town of Colle di Val d’Elsa, with dinner inspired by the flavors and traditions of Tuscan cooking.
DAY FOUR
The morning begins with a second in-person session with Dr. Christoph Helferich, building on the embodied work introduced on Day Two. Group coaching then focuses on priorities, helping participants clarify what matters most in their personal and professional lives, consider competing demands, and identify where they want to direct their energy and attention.
In the afternoon, the group travels to Val d’Orcia for a guided walk along the ancient Via Francigena outside Pienza. Walking and focused exchanges offer space to explore the morning’s insights, consider their implications for leadership, and connect clearer priorities with practical choices.
Back in Chianti, the day closes with a sunset wine experience and dinner together, allowing time for informal exchange and reflection on the day’s work.
