Leaders I work with

I don’t work with everyone.

I work with people who have already done the hard yards:

serious universities, demanding professional designations, and at least a decade in roles where the numbers and the stakes are real.

Think:

  • Degrees from places like Cambridge, Oxford, LSE, Rotman, Ivy League, top European or Asian schools

  • Designations such as CFA, FSA/FCIA, CPA/CA, JD, PhD, PEng, CBV, AIC, MRICS

  • Careers built in crucible cities like Toronto, New York, London, Hong Kong, Singapore, Zurich, Frankfurt

  • Or in outposts of major capital: Abu Dhabi, Doha, Luxembourg and similar

You’re already operating in serious systems: asset management, pensions, private markets, risk, corporate finance, regulation, advisory. You know what it means to be accountable.

And yet, for all of that, you still feel weirdly unseen.

You are my people if any of these three situations feels familiar.

1. Not (yet) in the seat, but clearly capable

On paper, you’re the dependable expert.

In reality, you’re starting to wonder: “Is this as far as I go here?”

You might:

  • Have 15–20 years at the same institution, carrying the heaviest work while others get the titles

  • Be the quiet person everyone runs to when things are complex or on fire

  • Watch consultants and louder colleagues influence decisions you quietly know how to improve

Common variations here:

  • The overlooked expert

    You assumed that if you kept solving the hardest problems, someone would tap you for real leadership. Instead, you’ve plateaued. The org relies on you, but doesn’t quite see you.

  • The “first in the family” professional

    You already did the impossible compared with where you started. Part of you feels ungrateful even imagining a different role or city. The weight of expectations makes every decision feel higher risk.

  • The loyal lifer

    One firm, many rotations. You know the plumbing end-to-end, but succession planning never seems to include you. The only way “up” looks like waiting for someone else to resign, retire, or be pushed out.

You’re not looking for motivation slogans. You’re looking for a clear, honest map of options, and a way to move without blowing up what you’ve built.

This is where we work together: unpack what you actually want, what your skills are worth on the open market, and what a realistic next step could look like in or out of your current firm.

2. In the seat, still doubting you belong

Here, you have the title: director, VP, MD, head of something, sometimes a C-role.

The comp is good. The responsibilities are real. The org chart says “leader.”

Inside, you’re less sure.

You might:

  • Feel that every mistake will confirm the quiet suspicion that you’re not “really” leadership material

  • Over-prepare obsessively, then still leave meetings replaying every sentence you said

  • Carry perfectionism, impostor feelings, or a harsh inner critic that never shuts up

Variations in this group:

  • The political casualty (fired, restructured, or sidelined)

    You’ve already been pushed out once. The new role is good, but the scar tissue is real. You’re wary, watchful, reluctant to trust senior colleagues again. Part of you is waiting for the next axe.

  • The values-conflicted leader

    You lead teams or capital, yet you’re increasingly uneasy about product, culture, or incentives. You worry that staying means slowly becoming someone you don’t respect.

  • The introverted leader forcing a persona

    You’ve been told to be “more visible,” “more charismatic,” “more like X.” You can perform that act for a while, but it’s draining and feels false. You’d like to lead in your own way without shrinking or pretending.

In this work, I’m not trying to turn you into someone else.

We look at:

  • How much of your doubt is internal habit vs external context

  • Where your quieter strengths actually serve the institution better than the loudest person in the room

  • How to speak, present, and influence in a way that fits your temperament, not a stage character

You may already have a therapist for trauma, anxiety, or family history. That’s important work. What I offer sits alongside that: a confidential, technically fluent thinking partner focused on your leadership, career, and the human costs of staying where you are.

3. At the apex, asking “Is this it?”

You’ve reached what younger you once dreamed of:

  • C-suite, partner, founder, senior owner, or substantial board responsibilities

  • Enough money that the spreadsheet says you’re “set”

  • Public markers of success: titles, deals, awards, sometimes acrylic plaques in atriums of downtown office towers or at university campuses

And yet there is a quiet question you don’t say out loud:

“Is this it? Is this what I traded my life for?”

You might:

  • Struggle to enjoy any win for more than a day before the next issue claims your mind

  • Notice hairline fractures at home: strained marriage, children who barely see you, no real friends

  • Be surrounded by people with agendas: staff managing up, peers competing, investors watching their IRR

Sub-types here:

  • The founder who outgrew their role

    The firm’s success is undeniable. Your joy in it is not. You’re still in every decision, yet increasingly suspect you’re not the right person to be in all of them.

  • The board-level or ICD-trained director

    You sit in judgement on management, sign off on risk, and feel the personal liability keenly. You wonder whether staying on certain boards is worth the long-tail reputational and ethical risk.

  • The exiled expert in a far-flung hub

    You run serious capital or teams in a place that looks glamorous on paper but feels isolating. You question how long you want to remain “on assignment” before something inside you hardens.

Here the work is less about climbing and more about reorienting:

  • What do you actually want the next decade to be about?

  • Which roles, boards, or business lines still deserve your time?

  • What are the real costs of staying on every committee and plane, and what would it look like to step back without disappearing?

This is not life coaching. It is sober, technically informed, morally serious conversation about the gap between your CV and your inner life.

A note on who you are

Across all three groups, my career and leadership clients tend to share a few traits:

  • Introverted or quietly intense. You think deeply, speak carefully, and often feel misunderstood in extroverted cultures.

  • Highly educated, often “first” in some way (first in the family to reach this level, first from your background in the room).

  • Rarely satisfied with shallow narratives. You care about how your work affects people, not just numbers.

  • Either under-celebrated or politely commoditized: everyone says you’re “valuable” but treats you like a row in a spreadsheet.

You may have tried therapy, coaching, or leadership programs. Some helped; some didn’t.

What you haven’t often had is a long-term, confidential confidant who:

  • Understands the technical side of your world

  • Respects the pressure of crucible cities

  • Is not shocked by what you actually think and feel

  • Has no agenda to sell you a formula, only to help you see more clearly and act more honestly

If you see yourself in any of this, you’re the kind of leader I quietly sit with.