Stewardship & Succession

For people whose decisions outlive their job title

At a certain point in a career, “what’s next?” stops being a question about your CV and starts being a question about everything.

You are not just thinking about a move. You are thinking about what happens to a firm, a book of clients, a mandate, or a team if you stay, step back, sell, or walk away. You are thinking about staff who trusted you, clients who rely on you, successors who may or may not be ready, and a lifetime of work that cannot simply be thrown on a spreadsheet and traded.

This is the territory of stewardship and succession. It is demanding country. You do not need a pep talk. You need a place to think clearly, with someone who understands both the numbers and the human cost of getting this wrong.

When your role is more than a role

If you are considering this kind of work, you probably sit at or near the top of something real:

  • A practice or firm you built and now need to hand on, sell, or reshape.

  • A large book of business in wealth, pensions, insurance, or advisory where clients know you, not just the logo.

  • A senior executive or CIO role where your exit will leave a genuine gap.

  • A key position inside a pension, insurer, asset manager, sovereign vehicle, family office, or regulator where decisions ripple through workers, retirees, and communities.

You know how to make financial decisions. You have done it for years. This is different. This is the intersection of:

What you owe to others.

What you want the rest of your life to be like.

What happens to the thing you’ve been entrusted with after you are no longer in the room.

There are no clean models for that.

The questions you can’t delegate

The conversations that belong here sound more like:

  • How long can I keep carrying this responsibly, in this body, in this season of life?

  • If I sell or merge, who actually wins and who quietly loses?

  • Who should follow me, beyond the obvious political choice?

  • What am I willing to trade for price, and what am I absolutely not selling?

  • How much of my identity is tied up in this role or practice, and who am I if I’m no longer “the one in charge”?

  • How do I step back without abandoning people who trusted me or clinging on long after my time is really done?

Bankers, lawyers, and internal stakeholders will each have their angle. The pressure will be to move quickly, keep things tidy, and “get the deal done.”

You are allowed to want something more honest than that.

Why have a partner in this

My role here is not to tell you what to do. You already live in a world full of strong opinions.

What I bring is a long view and undivided loyalties in your favour:

I understand mandates, funding, regulation, capital allocation, and how large systems behave under stress.

I also understand hairline fractures: spouses who have waited years for you to slow down, children who barely know what you actually do, staff who fear what happens when you leave, younger leaders who are half-ready and half-terrified.

I am not on anyone’s transaction fee, bonus pool, or internal promotion list.

We map your situation carefully: assets, obligations, promises, politics, health, family, faith, and the parts of you that are simply tired. We name the elephants out loud: pride, guilt, fear of irrelevance, resentment, duty, greed, love. We look at the decisions you are facing as a series of long-term trades, not just this year’s income statement.

The standard of success is not whether a press release looks good. It is whether, years from now, you can still tell the story of what you did without wincing.

How the work happens

This is not quick work, and I do not pretend it can be.

We usually begin in longer conversations, online or in person, where you are off-stage and fully off-record. No slides. No spectators. Just time to lay out the landscape as it really is.

From there, we move between three kinds of thinking:

Mapping

Clarifying what is truly fixed and where you have more room to move than you assume. Distinguishing between legal constraints, market realities, and stories you have told yourself for so long they sound like facts.

Scenario-testing

Thinking in decades, not quarters. If you stay. If you sell. If you step back gradually. If you say no to options that look attractive but do not sit right in your gut. Looking at second- and third-order effects on people, capital, and your own future life.

Commitment

Turning all of that into real-world moves: conversations with partners or boards, boundaries with buyers, clear messages to staff, and a plan for your own next chapter that is more than “I’ll play golf and see.”

Sometimes this work also involves a period of quiet shadowing. I may sit in on selected meetings, read your board packs and briefing notes, watch how decisions are framed and how people respond to you. Not as a judge, but as a detective: looking for patterns, blind spots, unspoken fears and loyalties that no dashboard will ever show you.

In parallel, you become a detective in your own life. You pay closer attention to what the people closest to you are already saying with their words and their silences: a spouse’s tiredness, a child’s offhand comment about “when you’re home,” a deputy’s nervous joke about succession, a colleague’s relief or dread when retirement is mentioned. You ask a few careful questions. You listen more than you defend. You start to see how your role really lands on the people around you, not just how it looks in your head.

We keep circling back to three questions:

  • Does this honour the people involved?

  • Does this honour the promises you’ve made?

  • Can you live with this when you are no longer the one signing?

Sailboat conversations

For some stewards, the thinking itself needs a different setting.

When it makes sense, we take this work out of meeting rooms and onto my classic blue-water sailboat on Vancouver Island for a private working retreat. It is not a luxury cruise. It is a quiet, weather-dependent space where:

Your phone is off or silenced.

There is nowhere to perform.

You are reminded, physically, what it is to live at human speed: wind, tide, daylight, fatigue, rest.

Time on the boat is for extended conversation, long silences, honest reflection, and emerging with a few clear decisions rather than a dozen half-hearted maybes. It is for leaders who understand that the next choices they make will shape other people’s lives long after they are gone and want to choose in a state of real alertness, not exhaustion.

These retreats are rare, scheduled carefully, and priced separately by agreement. The point is not the scenery. The point is the seriousness with which you give attention to what comes next.

A high bar for both of us

I do not offer this kind of high-trust assignment lightly. If it ever starts to feel routine to me, I will stop.

This side of my practice is for people who understand that stewardship and succession are not back-office topics. They are the culmination of a life’s work.

You bring your history, your responsibilities, your doubts, your hopes, and your willingness to think and act like a steward, not just an owner.

I bring my experience, my independence, my ability to see patterns and risks, and my commitment to stay with you until the decisions in front of you are fully faced and honestly made.

If you read this and feel recognised as someone who carries more than a job, and who wants to leave something coherent, not just maximised, this may be the right room.

From there, the next move is simple: we talk, we see whether we can work together at this depth, and if we can, we begin.