The AI Reckoning Is a Culture Shock. Every Leader Is an Expat Now.

Every Leader Is an Expat Now

The first time I led a team outside Canada, I packed my leadership style in the same suitcase as my winter coat. Neither turned out to be much use in Indonesia.

I started my leadership career in Canada. I knew how things worked there: how people disagreed in meetings, how decisions got made, what "yes" actually meant. I also knew how to use sarcasm, which Canadians treat as a second official language. That style worked. So when I got the chance to lead a large team in Indonesia, I assumed it would work there too.

It didn't. Not all of it, anyway. Sarcasm, for one, doesn't always survive the flight. What I meant as a joke could easily be taken literally.

The moment that really drove it home came early. I held an informal brainstorm with my leadership team. I enjoyed the discussion and thought nothing more of it. Six months later, reviewing the projects the team was working on, I found several fully funded initiatives that had come straight out of that session. What I'd thought of as thinking out loud, the team had heard as direction. I needed to be far more prescriptive about what was an idea and what was a decision.

The feedback came too, though not always in the form I expected. Early in my tenure, one of my team members pulled me aside and told me I was being too nice, and that people were more comfortable with a directive style. They didn't want me to turn mean or angry. But I had to adjust.

Those two moments shaped what came next. I developed a clearer, more directive communication style. I worked with the team on getting comfortable pushing back on me, so we could meet in the middle. And I spent more time understanding how the culture worked by simply asking people. Some of what made me effective in Canada travelled fine. Some of it had to be relearned from scratch. Figuring out which was which turned out to be the actual job.

I think about that assignment a lot right now, because every leader I talk to is being posted somewhere new without moving house.

The new posting

AI agents are changing how work gets done, and with it, how leadership works. It's a new culture, with its own norms, its own language and its own ways of making decisions. Most of us are arriving with a playbook written for the old one.

That's where the anxiety comes from. And it looks different depending on where you sit.

At the top, the anxiety is about getting it wrong in public. Boards want an AI strategy, preferably yesterday. In a 2026 survey by the enterprise AI company WRITER, 75% of executives admitted their company's AI strategy is more for show than real guidance. That's a lot of people nodding confidently in meetings about a plan they privately don't believe in. Most of us have done the nodding.

For leaders coming up, the anxiety is more personal: will there still be a seat for me? The numbers aren't soothing. Middle managers made up roughly a third of white-collar layoffs in 2023, up from about a fifth in 2018, according to a Bloomberg analysis of Live Data Technologies data. Amazon cut 14,000 corporate roles in late 2025, citing fewer layers. Gallup reports the average manager's team grew from 10.9 people to 12.1 in a single year.

Fewer managers, bigger teams, and a new set of tools nobody fully understands yet. If you're a senior manager wondering whether you're next, you've read the room correctly.

What the expat years taught me about this moment

1. Your home playbook feels universal until it isn't. In Canada, I didn't think I had a leadership style. I just had "leadership." It took a different culture to show me that my way was only one way. AI is doing the same thing to a lot of leaders right now. A big chunk of what many of us called managing (chasing updates, routing information, building the status deck) turns out to be coordination. Agents are getting very good at coordination. If that's where most of your week goes, better to learn it now than from a restructuring memo.

2. The locals see it before you do. My team in Indonesia saw my blind spots long before I did. I was used to an empowering, hands-off style of leadership, and I thought it was working. They knew I needed to be clearer and more directive, and they were right. The same is true now. Someone on your team is already using AI in ways you haven't figured out, and they probably have opinions about how you're handling it. Ask them, and mean it.

3. Some things travel. Some don't. What travelled from Canada to Indonesia: I wasn't going to compromise on being kind to people, or on helping them learn to speak up when I needed to be told what had to change.

What didn't travel, at least not at first: my expectation that the team would innovate and bring their experience to the table on their own. The same split applies with AI. The mechanics of managing work are changing fast. Judgment, accountability, developing people and holding the culture don't hand off to a machine. Microsoft's 2026 Work Trend Index found that organizational factors such as culture, manager support and talent practices account for 67% of AI's real impact, versus 32% for individual behaviour. The human part of leading is the part that carries.

4. You have to learn the new language. Leading in Indonesia meant learning Bahasa, but also the cultural nuances, the superstitions, and even Big Two, the card game. Leading alongside

AI has its own vocabulary: who decides what, when an agent acts on its own and when it checks with a person, and who owns the result when something goes wrong. Most organizations haven't answered those questions yet. That's a gap, and gaps are where leaders earn their keep.

5. The assignment ends. What you built shouldn't. Expat postings are temporary by design. Everyone knows you're leaving. So the real measure of the job is how things run after you're gone. By the end, my team had the confidence to speak their minds and push back when it made sense. And I'll admit I smiled when some of my shyest, most junior team members started making respectful, sarcastic comments at my expense. Some things travel both ways.

That's the principle I keep coming back to in this AI moment: build a system that survives you. For a leader today, that means redesigning your team for a world where some of the work is done by agents.

Decide what agents handle, what people handle, where the human check sits, and who answers for the outcome. Do it before someone does it to you. Leaders who propose the new operating model get to shape it. Leaders who wait tend to get reorganized by it.

If you own the business

Owners are usually the wise locals, like the people I depended on in Indonesia to give me direction and show me the lay of the land. In this new posting, even the locals are new arrivals.

The owner's version of the anxiety is quieter, and it tends to show up in the middle of the night. AI is moving faster than most of us can follow. A competitor that didn't exist last spring can launch with three people and a stack of agents, and undercut you on the work you've always been known for. You think you know what your business is worth, but you're less sure what it's worth if the ground keeps shifting. You suspect AI could save you money or open new doors. You also suspect it could quietly make part of what you sell less valuable. And you're not entirely sure which parts are which.

Then there's the question nobody has asked you yet, but someone will: a buyer, a successor, a banker. What does AI do to this business? Is this a company using these tools to get stronger, or one about to be disrupted by them? If you can't answer that, they'll answer it for you, and price it in.

Most of those worries come back to the same few questions. Where does our value actually come from? How much of it depends on me? What would a competitor with better tools find easy to copy? Those are the questions a buyer asks, AI or no AI.

You don't need to understand every tool to start answering them. You need to know which parts of your business would hold up and which wouldn't.

And every task you hand to an agent has to be explained first: what good looks like, who decides, what happens when it breaks. You can't delegate to an agent what only exists in your head. You couldn't delegate it to a person either, which is exactly why buyers discount businesses that run on their owner.

So the work that gets a company ready for AI is mostly the work that makes it worth more. Decisions written down. Ownership clear. Knowledge spread past the two people who've been there forever. A clear reason customers choose you, one a new competitor can't copy over a weekend. The Value Builder System™ calls these Hub & Spoke and Monopoly Control, and Curtis Scaplen put both under the magnifying glass last week. AI didn't create these risks. It just made them harder to hide.

The reckoning

We're at a leadership reckoning, and I use that word on purpose. Some leaders will lose roles no matter how good they are, because a lot of flattening is about cost, not merit. Being relevant isn't the same as being safe.

But the anxiety has a direction. I arrived in Indonesia with the wrong style. Most people in a new culture do. What mattered was how quickly I was willing to listen and adjust.

Arriving naive is forgivable. Staying naive is the problem.

Next week we discuss: if AI does the first drafts, where does the next generation of leaders learn judgment?