You have climbed far enough to know that what would move you now is not more skill, knowledge, or experience. It 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. Chief executives, founders, senior government. People at your level and carrying your kind of weight, who want to see what is really going on, and the part they play in it.
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, where the circle first forms. The ten months that follow unfold one day a month, in Dubai.
Umbra leaves you with three things: the reading of yourself that your position no longer allows anyone to give you; the ability to see what is really going on in the rooms you lead, including your own part in it; and eleven peers who want nothing from you, which is why they can afford to be honest.
You leave every gathering in a stronger position than you arrived. Umbra is not designed to make you doubt yourself. It gives confidence better foundations: wider sight, then clearer action.
- —Your own account of how you came to lead, told to eleven peers and heard. By the end of four days you know what you brought to leadership long before you led anyone, and which of it still directs you.
- —Eleven people who know you beyond your title. Four days away from the office does what months of single meetings cannot.
- —A first unvarnished view of how you operate among equals: how you go after influence, how you handle being one of twelve, what you do when the group does not go your way.
- —What you are there to work on this year, in your own words, settled in a private conversation with one of us after the retreat.
- —One specific commitment for the month ahead, stated to the group and witnessed by it. The following month, you bring back what happened.
- —If you brought a situation, the group’s reading of it: questions and hypotheses rather than advice, and a clearer next step.
- —One thing you are taking with you and one question you are still holding, named before you leave.
You can read what you could not read before:
- —How you take up authority, and when you avoid it.
- —The moves that protect you under pressure, caught in time.
- —What people attribute to you because of your position, apart from what you actually did.
- —When a team has become dependent on you, or has turned to fight or flight, and how to shift it.
- —How authority, face and loyalty work differently across Gulf and Western colleagues, and how trust is built across that line.
- —What is yours, and what the organization places on your role.
- —How to hold a decision open without the team losing its nerve.
- —What your organization is avoiding, and how to name it.
- —What you wish to leave behind, and what to let go of.
- —What you keep doing, what you stop, and what comes next.
The people around you notice it as the real issue named in the meeting rather than after it, bad news that reaches you sooner, the argument that keeps returning to your team no longer returning, and fewer of the reactions people brace for. By the end of the year, you lead deliberately rather than by default.
And you keep eleven people outside your organization who know how you operate, whom you can call about what cannot be discussed inside it.
Most of the day is conversation, but not the kind you have at work. There is no deal to win and no boss to answer to. Status still comes in with everyone; here, it gets noticed instead of obeyed.
Nothing is taught from the front of the room. The twelve of you, and what happens among you, are the material. One full day each month, the same twelve people, no guests. Every day has three parts.
I. DisruptionIn the morning
A short input from us, an idea, a question, sometimes an exercise, that unsettles the explanations everyone walked in with. It is not a lecture.
II. DigestionFor most of the day
One or two members bring something current: a decision they keep postponing, a relationship that has gone wrong, a board they cannot read. The group takes the time it needs instead of rushing to a fix, which is what the name means. Nobody gives advice. People ask, offer a reading, and say what they notice, including how the story lands in the room: who rushes in to rescue, who goes quiet, who takes a side. Those reactions often mirror what happens around the situation at work. The moment that matters is often when someone realizes they have just done, here in the room, the very thing they came to talk about.
III. ReconstitutionAt the end
Stepping back into your role with what the day showed you: time alone to write down what surfaced, then one specific commitment for the month, said to the group and witnessed by it, and a last round in which each person names one thing they are taking with them and one question they are still holding.
Between gatherings
A private thread for the twelve, for the questions you cannot put to your board or your team. No reading lists, no homework.
Before Italy
A private conversation with one or both of us, so that you arrive knowing what you are there to work on rather than spending the first day finding out.
Italy, four days
The circle forms at the Badia di Valfabbrica, a monastery that has stood in the Umbrian hills for a thousand years, on the old road between Assisi and Gubbio. Away from the office, twelve senior people become a group. Short inputs from us open each part of the day; the rest is the room, and walking and thinking in the hills. Long dinners together. By the end, people are known by what they say and do in the room, not by their position.
After Italy
A private conversation with one of us, to turn what surfaced in Umbria into something you run in your own role and organization.
Dubai, ten gatherings
One full day a month, the same twelve. The year moves outward. First you: how you use authority, and what you do under pressure. Then the people around you: power, trust and rivalry. Then the organization: what it asks of you, and what it avoids. The last months come back to you: what you keep doing, and what you stop. The order adapts to what the circle needs. The April circle breaks for July and August.
The end
The circle closes after the tenth gathering, as agreed at the start. The thread, and what the twelve choose to continue, carry on.
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.
Comparable authority, comparable exposure. No client and supplier pairs, no direct competitors, nobody junior in the room. We check this before anyone is accepted.
- —You hold real authority: when you change, an organization feels it.
- —Or you have built and exited, and want to think at that level among people who want nothing from you.
- —You are curious about your own part in what keeps recurring around you.
- —You can say “I don’t know” in front of peers.
- —You have done the executive programs. The returns have flattened, and another course will not move you.
- ×You need the room to know how senior you are.
- ×You want advice, a framework or a certificate for your team.
- ×You are looking for a network, an audience or a stage.
- ×You would change the people around you, but not yourself.
- ×You cannot protect fourteen days across the year, four in Italy and ten in Dubai, plus travel. A missing member changes what the room can do.
Umbra is not for everyone. These two lists are here so you can tell before we speak.
We never publish who is in a circle, before, during or after. Nothing said in the circle is repeated outside it, by us or by its members; everyone agrees to that at the outset. Whether you mention Umbra to anyone is entirely your own affair.
Two people convene the circle, and they came to this work from opposite directions: one from inside global companies, the other from inside government.
Both trained at INSEAD in systems psychodynamics, the study of what drives people and groups beneath what they say and do. Both are in the room for all four days in Italy and every gathering in Dubai. Not a faculty. Not associates. Us.
Thirty years with large multinationals, across nine 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.
More than twenty-five years transforming organizations 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.
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.
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.
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.
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.
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.
Massi advised us through a period of serious transformation in how we develop our people. What I valued was his ability to see the whole picture, to pull the pieces together, and to put the path in front of leaders in language they could act on. He listens differently. He hears what is not being said and has the courage to name it, gently and without flinching.
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.
Wissam listened to the challenges we were facing and was able to identify patterns that were reinforcing certain behaviors and outcomes that we were trying to change. He has an ability to read the system around the problem. He also says those things in a way that enables us to act rather than defend.
A circle only works if it stays whole.
Twelve places in each circle. We speak with every person, and we turn people away, because getting the twelve right matters more than getting to twelve.
- 1Request the details. The fee and the practical details come with them.
- 2A private conversation with one or both of us. Nothing is sold on it; we answer whatever you need answered, and both sides decide whether it fits.
- 3If it fits, a place is offered.