Umbra Umbria, Italy · MMXXVI
um·bra
/ˈum.bra/ n. f., Latin: shadow
Every light casts a shadow. Our tendency is to focus on the light, it's more fun there. But the shadow holds powerful truths. It contains the dynamics you may not see, but others experience.
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.

Umbra 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.

People who know them

No one has sat in this circle yet.

These are people who have worked with one or the other, over years and at close range, asked to say plainly what they saw.

I came to Wissam at a career crossroads, anxious about what would come next. I assumed coaching would help with the objective side, mapping options and planning steps. I did not expect it to work through the emotional side, even though the two are clearly linked. Understanding the roots of what I was feeling gave me the space to make decisions with clarity. I am in a very different place than when I started.

Michael Matly
Managing Partner, 111 West Capital

I trained as a coach at INSEAD, and I had the privilege of doing it beside Massi. What I saw in him has stayed with me since: a rare depth, and an instinct for what is truly happening beneath what is said. Having built a business and learned this craft myself, I know how uncommon that is, and how much it matters at the top. I would send any leader I care about to him, without hesitation.

Sir Richard Harpin
Founder, HomeServe

I assess senior leaders for a living, and I have known Massi for decades, first as his manager and long since as his friend. What has never changed is his honesty and the depth with which he reads people. He carried the weight of leadership himself, and it is that lived experience he now brings to the leaders he works with. Few combine so much substance with so much humanity.

Christian Vasino
Founder and CEO, Chaberton Partners · former CHRO, Adecco Group

I have watched Wissam facilitate group sessions for senior leaders, and what strikes me every time is his capacity to hold the room. He creates a space where senior leaders feel safe enough to be honest about their doubts and what they are really navigating, and he does it with a steadiness that never forces. He creates the conditions, and the insights emerge on their own.

Sandra Salame
Founder and CEO, Siira · General Manager, Crestan

Massi and I came through the INSEAD Executive Master in Change together, so I know the tradition he works in and what it takes to do it well. He reads the whole system, not only the person in front of him, and he does it with an integrity you feel at once. That combination is rarer than it sounds.

Tareq Alangari
President, Lenovo Middle East, Turkiye and Africa

I led Massi at ADNOC, so I saw how he works from the inside. He listens differently. He hears what is not being said and has the courage to name it, gently and without flinching. Leaders at the top rarely have anyone who can do that with them, which is exactly why a room like this matters.

Aseel Hamoodi
SVP Human Capital, ADNOC Group

I did not meet Massi as a coach. We built a company together, so I have seen him under pressure, in disagreement, and in the moments that actually test people. He notices what everyone else misses, the thing sitting under the conversation, and he builds the kind of trust where the real things finally get said.

Raluca Epureanu
Founder and CEO, FlairMakers

A circle only works if it stays whole.

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