Oltre Umbria, Italy · MMXXVI
ol·tre
/ˈol.tre/ prep., avv.
From Latin ultra. Past a given point; on the far side of what limits the view. In practice: what is there all along, and only becomes visible once you are willing to look past the thing in the way.
12 senior leaders. 10 months. 1 retreat.
Coming soon, Fall 2026.
You'll know if this is for you.
Convened by
Massimiliano & Wissam

You have climbed far enough to know that the thing limiting you now is not skill, knowledge, or experience. What is limiting you is something harder to name.

A pattern you keep repeating. A room you keep misreading. A version of yourself that shows up when the pressure is on, and that you are not entirely proud of. You have sensed this for a while. You have just never had the right place to look at it honestly.

Oltre is that place. Not a course. Not a coaching engagement. Not a networking dinner with a keynote. A small group of senior leaders — CEOs, founders, C-suite — people at your level and carrying your kind of weight, who have decided that getting to the next level means getting underneath the surface.

Once a month, you step out of the noise to work on the real thing. It begins with four days together in the Umbrian hills, inside the walls of a monastery that has stood a thousand years (and we mean it literally!), where the circle first forms. The ten months that follow unfold one day a month, in Dubai.

12
Senior leaders
10
Months
1
Opening retreat

Built for people at the top of a system.

Founders, chief executives, and senior government leaders. What they share is not a sector. It is the seat. No hierarchy in the room.

This is for you if
  • —You hold real authority — the kind where changing your approach is felt across an organisation.
  • —You have achieved what you set out to achieve, and something still feels unresolved.
  • —You are building something bigger than yourself, and want to lead from that place.
  • —You are willing to be honest in front of peers, including saying "I don't know."
  • —You want peers who carry the same kind of weight, not a classroom of strangers.
  • —You are done with programmes that leave you more informed but no different.
It is not, if
  • ×You need the room to know how senior you are.
  • ×You want to be told what to do.
  • ×You are not willing to look at your own part in the patterns you want to change.
  • ×You are looking for a course, a certificate, or a framework to take back to your team.
  • ×You are looking for a network, an audience, or a stage.
  • ×You cannot protect ten full days across the year. Attendance here is not optional.

The only entry requirement is the willingness to be honest about what is actually going on.

The work begins on the road in.
The arc of the year

I. The self

Authority and how you carry it. The patterns that run you under pressure. The effect you have on a room before you speak.

II. The relational

Power and what it costs. Trust across difference. The dynamics that form in any group under strain.

III. The systemic

What the system asks of you. Leading before the answer has arrived. The undercurrents everyone feels and no one names.

IV. Integration

What you carry forward. What you set down. What you leave behind when you go.

Who holds the circle

Two people convene this circle, and they come at the same work from opposite directions.

Both are trained at INSEAD in the systems psychodynamic tradition, the Tavistock lineage that works with what drives behaviour, not only the behaviour. It is the discipline behind everything that happens in the circle. They share one conviction: the group in the room is the instrument, not the audience. Both still do their own version of this work, and neither teaches from above it.

Massimiliano
Massimiliano

Close to three decades with large multinationals, across eight industries and three continents. He has spent that career reading people and systems, listening for what is spoken, and for what is left unspoken. He brings that ear, and the instinct of someone who has lived the pressures from the inside, to his coaching of chief executives, founders, and their teams.

Wissam
Wissam

More than twenty-five years transforming organisations from inside government. He co-designed the institutional and governance structures of Dubai Government, and spent over a decade at the UAE Prime Minister's Office rebuilding the machinery of federal government. He has advised and coached cabinet ministers, directors-general, boards, and chief executives across the region.

A circle only works if it stays whole.

Full attendance, agreed in advance. Oltre opens in Fall 2026 (most likely the first half of October) in the Umbrian hills. Twelve seats, by conversation.