Where a leader’s vulnerability actually begins
In my experience, a leader’s vulnerability rarely begins as a choice. It usually begins when something breaks them: a serious illness, the loss of someone they love, a life event large enough that they can no longer look away from who they have become. The harder truth is that most leaders feel it long before that, and spend years making sure the moment never arrives.
That is the uncomfortable starting point for everything I believe about leadership in an AI world, because the willingness to be seen as you really are is the foundation the rest of it sits on. So it is worth being honest about where that willingness actually comes from.
It usually takes a crisis, and it is usually late
Most of the leaders I have watched reach real vulnerability got there in their fifties or sixties, after something shattered them. A diagnosis, their own or one belonging to someone they love. A loss. An event that made them stop and admit, often for the first time, that they were not the person they had spent decades convincing the world they were, and that they did not much like who they had become.
And it nearly always comes late. If that same honesty had been there in their thirties, think of what they could have built, and who they could have spared. By their fifties and sixties there is a great deal that cannot be undone. That is the quiet tragedy I see most often: not that leaders never face themselves, but that they wait until the cost of avoiding it is higher than the cost of doing it.
It is not only men
It is not only men. I have met women at the top carrying the same thing, having proved themselves in rooms built to doubt them, and having given up a great deal to do it. The common thread across all of them is simple and sad. They do not like the life they ended up with, even as they work hard to make sure no one can tell.
The emptiness most of them already know
They will tell you, and tell themselves, that they like who they are. But in the quiet moments, when the celebrating stops and the house goes silent, many find very little underneath. Not much that is truly theirs, and a short list of people who are there when things are not going well. They sign thousands of paycheques and can call almost none of those people when they need a hand, or a hug, or simply someone to talk to.
In my experience, most leaders sense this about themselves. What it takes to make them act on it, even to begin thinking about it honestly, is usually a life event big enough that avoidance stops being an option.
The decisions they never talk about
Part of what they are avoiding is a quieter account than the public one. The ideas they said no to. The risks they declined. The changes they could have backed and did not. We reward leaders for the money they save by saying no, and we almost never ask what saying yes would have built, or who it would have reached. That is the question I have watched leaders work hardest to avoid: in that meeting, that year, had I said yes instead of no, would things be different now?
Why this is the root of AI strategy, not a detour from it
This is not a soft tangent away from AI. It is the root of it. A leader still protecting the performance asks the safe questions, of their people and of the technology, the ones that keep the story intact, which is the surest way to end up asking AI everything except what actually matters. A leader who has faced themselves can ask the real ones. That honesty is also what tells you who is actually fit to lead the work, and it is how the people who should be leading start to step forward. The person who genuinely does not mind being seen as they are is the one who gets something real out of this technology. The one still performing will use it to protect the performance.
If you are a leader who feels this and would rather not wait for the event that forces it, that is the work I do with a limited number of senior leaders each quarter. Work with Thomas
Questions this article answers
When does a leader usually become vulnerable enough to change? In most cases I have seen, not by choice, but after a life event large enough to break through the performance: a serious illness, a loss, something that forces an honest look. The willingness is rarely chosen in good times; it is usually forced in hard ones.
Do most leaders sense something is wrong before a crisis forces it? Yes. In my experience most leaders quietly know that the life they built has little underneath it, and that they do not much like who they have become. They simply spend enormous energy making sure no one sees it, themselves included.
Is the cost of avoiding this only personal? No. The same avoidance shows up in the decisions, in the ideas and risks a leader says no to in order to stay safe and unseen. The personal account and the professional one are the same account, which is why facing it changes both.
Why does this honesty usually arrive too late? Because the longer a leader performs, the more they have invested in the performance, and the higher the perceived cost of dropping it. By the time a crisis forces the reckoning, decades of decisions have already been made on the old terms, and much of it cannot be undone.
What does a leader’s vulnerability have to do with AI? Everything. A leader protecting an image asks AI and their people the safe, self-protecting questions. A leader who has faced themselves can ask the real ones, which is the only way the technology produces anything beyond a polished version of the past.
Thomas Anglero is a Strategic AI Advisor (MerkabaPhi AS, Oslo), with 450+ keynotes across 30+ countries. Enquiries: anglero.com.
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