In a monarchy, there is rarely a leadership vacuum. The principle is simple: one ruler leaves, another is immediately in place.

It may not be a perfect comparison for business succession but I’ll argue that it’s a useful one. The best organizations do not just prepare for the next leader but for the next several leaders, and for the world those leaders will inherit.

What struck me in the conversation with McGill management professor Karl Moore, a former teacher, is that not all CEOs really think about legacy. Great CEOs and entrepreneurs do.

It is not a given that leaders will properly think about their immediate replacement, let alone two generations down.

Karl is a CEO whisperer of sorts, a brilliant prof who brings business leaders into the classroom to inspire students. He’s host of The CEO Series radio show and podcast, and was recently honoured in the Canadian Senate for his “enriched public discourse... translating rigorous research into accessible insight”. He’s written more books than I’ve managed to keep track of, and his latest is We Are All Ambiverts Now: Introverts, Ambiverts, and Extroverts in the C-Suite.

He feels too many leaders still underestimate the youth.

This is where thinking like a monarch can make some sense. It is not just: what happens when I die? It is closer to: this kingdom has existed for a long time, and the work is to make sure it can continue long after me.

For businesspeople, succession planning is usually treated as a late-stage exercise, something to revisit once the company is larger, the children are older or retirement is closer. Framing estate planning in a legacy-planning context can help organizations build generational resilience, not unlike royals.

Why Family Businesses are Stronger

Moore’s broader point is that legacy-building is not passive.

One of his observations is that family businesses often outperform because they are forced to think in longer time horizons. Public companies and non-family firms are generally more sensitive to market or stakeholder pressures. Family businesses tend to think beyond the quarter and take responsibility for people they’ve never meet or haven’t been born.

“The big advantage of the family business is the long view,” and it can be as strategic as it is sentimental. Many of these companies are trying to preserve something that will matter to children, grandchildren and future stewards of the business.

Business succession and estate planning are therefore tightly connected, or at least should be. If the company is truly meant to outlive one person, the plan cannot only be personal but structural.

Double Down on Youth

His argument is not that youth should automatically run the show but that younger employees often see change earlier, and more clearly, than those at the top.

“You need to listen to young people, frontline troops, who are dealing with the harsh realities of today’s world,” he said, adding that businesspeople mustn’t be “cut off from reality” if they expect their organizations to remain agile.

That is where his emphasis on reverse mentorship becomes so pertinent, especially with the rise of AI and sophisticated media platforms that are totally foreign to GenXers like me.

Since succession planning is about developing a deeper layer of leadership, in practical terms, that means involving younger leaders before a transition becomes urgent, listening to them seriously in executive meetings and giving them the chance to shape the business rather than merely inherit it.

This is also where the monarchy analogy has limits. In business, continuity cannot only mean preserving the institution exactly as it was. As we recently explored with the Armani estate, some estate plans protect families while keeping them away from business operations.

The New ‘VUCA’ Economy

Moore describes today’s economic environment as a “VUCA World”: one defined by volatility, uncertainty, complexity and ambiguity. It is a useful framework because it captures why old leadership habits are becoming less reliable.

In a VUCA economy, it is no longer enough to have a fixed plan and a commanding executive style. Leaders of our generation need more agility than ever.

“I think a number of CEOs fall short that way,” Moore said, “because they’re a bit stuck in the old way of doing things. Partly because when they were young, that’s what a CEO did… you looked at the person above you and did what they did, because that’s what a CEO did. But in a world that’s moving… we’ve got to be a bit different than we were 10, 20 years ago.”

This may be one of the harder lessons for founders: The habits that built the business may not be the habits that preserve it.

Knowing Karl first as a professor and then later speaking in his CEO class was quite the honour. What he has built is not only a brilliant academic career but platforms with an almost infinite source of material, relationships and learning, while also giving leaders a structured way to spread their own learnings.

Karl, to my knowledge, did not inherit a monarchical structure to manage his professional legacy. Over decades, he put the work in and created one; an information ecosystem that serves students, executives, institutions and future researchers. He has become a king among Canadian business thinkers, and deservedly so.

When Giorgio Armani and partner Sergio Galeotti decided to sell their Volkswagen Beetle to finance a startup design house in 1975, it’s safe to assume that estate planning was not top of mind.

Half a century later, Armani would be mourned as one of the most successful and culturally impactful fashion moguls in history, leaving behind an empire worth more than $10 billion US across clothing, home furnishings, perfumes, cosmetics...

The estate plan now being watched by experts is not a simple one. It restricted the list of potential buyers and created guardrails around how beneficiaries could sell their shares.

Is this ultimately what he would have wanted, or a case of over-planning? The jury is still out. The structure may prove to be genius, or it may also hurt the value of the assets.

Armani’s estate plan feels like part of Italian cultural heritage, and artisan-run businesses may not fit nearly into the estate models shaped by European and North American capitalism. Rather than maximize value, sell to the highest bidder and move on, there can be a more complex mechanism to attempt to preserve continuity after an exit of some kind.

For David Lenok, senior editor at WealthManagement.com and host of the podcast Celebrity Estates: Wills of the Rich and Famous, the Armani story stands out because it isn’t the usual cautionary tale.

Listen to David Lenok on The End Game podcast

“I’m always happy when I get to do an episode that’s not about an estate failure,” he said, breaking down Armani’s plan on The End Game. Often, “if a plan works, you don’t hear about it.”

Intentional Design

A pioneer of the power suit, Armani’s estate interestingly did not reflect his trademark minimalism.

Some experts are already warning not to emulate its complexity. Lenok’s overall takeaway is that Armani’s intentionality wasn’t simply about preserving control from beyond the grave; it was about building a structure that could survive real-world pressures after the founder’s death in September 2025.

One practical example he highlighted was how the plan offered various options for beneficiaries to sell their shares but included guardrails, like details on how to sell and to whom. Rather than dictating a single outcome, the structure offered flexibility inside defined perimeters:

· Scenario Planning: Not a template but a deliberately pre-engineered organizational roadmap.

· Defined end-state: Setting the direction without locking successors into a predetermined transaction with one buyer.

· Stewardship by competence: Family members were given shares in the business without full control, ensuring that brand continuity is operational, not just symbolic.

Armani’s plan, in Lenok’s telling, emphasized placing “trusted friends in charge instead of family members.” Stewardship wasn’t assigned by default. It was assigned to people with the credibility and likely the competence to protect the brand and its culture.

Separating Family from Business

Armani’s planning is also a window into an emerging trend among high-net-worth families: separating who benefits financially from who controls the enterprise.

Lenok described “this idea of bifurcating the control of the company from what’s funding the livelihood of your family and your other heirs.” In Armani’s case, the family still profits but their support is not tied to managing the brand or holding a controlling stake. Instead, “there was a separate amount of money set aside for them… to make their lives easier, and to show his love for them.”

These structures are gaining in popularity since many estate conflicts are about more than money. They can also be about identity, authority and status. When business control is automatically distributed among heirs, families can inherit a governance problem while they are grieving.

Lenok’s view is that this bifurcation strategy is gaining steam as a best practice, even if it is emotionally difficult for founders.

“It’s hard… especially for first-generation wealth creators who think of these businesses as their children… to make that sort of severance,” Lenok said. But he also called it “a really elegant way to sidestep a lot of the problems of ending up with… people in positions where they don’t necessarily belong.”

The scalable takeaway for entrepreneurs is straightforward: if the business is your legacy vehicle, consider governance as a separate discipline from inheritance. You can support your family without forcing them to run your company or fight over it.

Design the plan with the same seriousness used to design the company.

Two Pillars of Successful Estates

Lenok joked that, on his podcast, “no matter what crazy estate we’re talking about… it always just kind of comes down to… we could have avoided all this by just talking to each other?”

Armani’s plan is unique in its scale but it cannot yet be deemed a success. After 100+ podcast episodes and estate investigations since 2019, Lenok said he is able to condense the lessons learned into two categories:

• Flexibility: Acknowledging that an estate plan is a living document because life happens and things change—“without any sort of changes or flexibility, it is a little ridiculous on its face.”

• Communication: Considering the human complement to that legal architecture—estate conflicts are “a lot more of a psychological affair than… a dollars and cents one,” and that managing expectations is often the real work.

The caution for business owners is not that complexity is wrong. Some businesses require complex structures. The caution is that if there is going to be a transition, it is usually better to start before you die. Otherwise, you may simply be prolonging the difficult part and making it more painful for the people who have to handle it.

If true business legacy is important, it is usually planned decades in advance. It is structurally embedded through governance, ownership, leadership development and communication. The will may not be the right mechanism to create a business legacy from scratch.

Armani’s estate may prove to be a rare public case where design, governance and communication were handled with the same level of care as the founder’s business operations.

For now, it remains a fascinating test case.

Five years ago, I decided to shake up my career, and joined Alex and Pascal at the helm of a little Canadian fintech startup making one very bold statement: We must take end-of-life planning seriously.

We have always been completely unserious, even chaotic in the management of the final phase of life. You and I as individuals, our governments, our financial institutions…

With this historic neglect, we have been in effect creating post-facto burdens for ourselves as seniors, and later for our surviving children, spouses, siblings and other loved ones during some of the most difficult moments of their lives.

As I reflect this summer on lessons learned along the journey thus far, one important bit of wisdom came from emergency medicine and critical care expert Dr. Daren Heyland.

Quoting the country singer Tim McGraw, Dr. Heyland suggests very bluntly that we “live like we’re dying”. And administratively plan for it.

After years of seeing the consequences of incomplete estate planning first hand, Dr. Heyland founded the Plan Well Guide to improve communication tools around serious illness. During COVID, after struggling to change the healthcare system from within, he went public with a pledge to help “capacitate you,” so people could better understand ICU care, the decisions that are made, and how to avoid serious pain and discomfort.

Listen to Dr. Daren Heyland on The End Game podcast.

Avoiding “Pull the Plug” Dilemmas

The phrase “pull the plug” often evokes scenes of heartbreaking, distressing and seemingly rare healthcare scenarios involving critical end-of-life decisions that have to be made by family members.

For others, the phrase may bring cold comfort: Don’t worry about my estate plan. If anything happens, just tell them to pull the plug.

Estate planning is not just for the dying.

Parts of an estate plan are meant to serve someone who is alive but incapacitated; unable to express their preferences, unable to explain how or where they want to be cared for, and unable to guide the people suddenly asked to speak for them.

Pull the plug is not a plan. For seasoned physicians like Dr. Heyland, who in fact teaches aspiring emergency physicians at Queen’s University, these scenarios are common and much more complex than anyone expects.

In an emergency, families may be pushed toward decisions framed as a yes/no choice: continue treatment or stop. But Dr. Heyland argues the better question is: what would the patient have wanted, given the trade-offs?

He notes that without preparation, families and clinicians “struggle to discern… the voice of the patient,” especially when multiple relatives must agree or disagree under stress.

Planning helps here in a couple of ways: it identifies who should speak, and it equips that person with the patient’s values and preferences. Without that, clinicians may rely on vague cues (she’s a fighter!) without knowing whether the family understands what “fighting” may actually mean in a medical context.

A person may want every possible intervention. Another may prioritize comfort and dignity if recovery would mean a life they would find unacceptable. Someone else may accept significant pain or dependency if it means more time with children or grandchildren.

Those preferences may also change over time, which is why we consider an estate plan that has gone without updates for over three years to be out-of-date.

The view one has at 30 may not be the view one has at 50 or 70. That is why this planning needs to be refreshed, and why the conversation matters as much as the document; we recently launched The End Game podcast series as well on this premise.

Elements of an Advance Serious Illness Plan

Unfortunately, effective incapacity planning cannot be accomplished with one signed form or a will template. It is a structured way to document values and preferences.

A practical plan should include:

● Decision-maker(s): Who will decide medical care and personal care if capacity is lost.

● Quality-of-life preferences: What outcomes feel acceptable, and what outcomes would be “worse than death,” in the patient’s view.

● Values under uncertainty: Preferences that hold even when no one can predict the outcome—because “there’s always this risk…”

● A “dear doctor” letter (optional): A plain-language summary of the person’s priorities: what matters most, what they fear, and what they would trade to extend life or preserve quality of life.

These questions do not require medical knowledge, just some foresight, effort and honesty.

Face Death Like an Adult

If you could no longer recognize the people you love, would you still want every possible medical intervention? If you could live longer but needed full-time care, would that be acceptable? What would make a life feel meaningful enough to keep fighting for?

These are tough questions that aren’t especially pleasant to contemplate but they should be considered part of our basic duties as adults, like doing your taxes.

We’re going to attempt, through our writing and podcasting, to push people to tackle end-of-life issues head on. Storytelling can be a powerful device to further these reflections, especially when the stories are true.

Early in his career, Dr. Heyland recalled caring for a man who went to work one day, suffered a catastrophic brain aneurysm and ended up comatose in the ICU, on breathing machines, with an extremely poor prognosis.

His wife was devastated, not only by the prognosis but by the fact that they had argued that morning. She had said hurtful things as he left for work. And she would never have the chance to say she was sorry, or that she did not mean it, or that she loved him.

The lessons Dr. Heyland drew were both practical and philosophical: relationships matter.

Yes, it is about instructions, wishes, documents and decision-makers. But it is also about goodbyes, unresolved conversations and how we treat the people around us before a crisis removes the chance to say what needs to be said.

Incapacity planning is not pessimism. It is personal risk management. It protects families from medical miscommunication, conflict and unnecessary heartache. It also protects the person at the centre of the plan by making sure preferences are captured, and that the final phase of life is lived in a way they would have wanted.

The lesson seems obvious but it is worth saying plainly: incapacity planning, estate planning, have to be done before incapacity. Afterwards, it is just too late.