This today is a very personal story; one I experienced during my senior management years in an EMEA role. It serves as a flashback triggered by recent conversations with many senior leaders who have scheduled coaching sessions with me.
The boarding gate closes behind you. Dubai fades into the amber haze below as you press your forehead against the cold oval window. Suddenly, the inevitable thought surfaces: "Was that the last time?"
You've just spent three days in your regional office. Back-to-back sessions, a town hall, dinner with the leadership team. On the surface, everything ran smoothly. But beneath the restructuring rumors that have circulated for six months, you felt them in the room. In the careful phrasing of questions. In the eyes of those who depend on you, to whom you have built an everlasting relationship, the whisper in the boardroom isn't subtle anymore: the operating model is being redesigned, AI is rewriting the efficiency calculus in real time, and headcount decisions are being made at a speed that would have been unthinkable two years ago.
And so, the question lodges itself, not dramatically, but quietly, like a stone in a shoe:
"Is this the last time I will walk through that office? Is this the last time this team will look to me as their leader?"
It doesn't stop there. Next week, you board a flight to the global leadership summit. You've attended for nine years. You know the agenda, the politics, the seating. But the new VP, brought in from outside, with an unclear mandate and a personality still being decoded, will be in the room. In this era, a hero-to-zero can happen between leadership cycles. One wrong read of the room. One misaligned priority. One restructuring PowerPoint that renders your division redundant before the coffee gets cold. Will this be the last leadership summit I attend as part of this team?
Then there's the quarterly business review. You've survived seventeen of them. But survival isn't the same as certainty. The models have changed. The metrics have changed. The board is asking questions that didn't exist eighteen months ago, questions shaped by AI-generated scenario analyses and geopolitical stress-testing that no amount of human intuition can fully outsmart. Your numbers are solid. But in this climate, solid is no longer a shield.
And somewhere between the Quarterly Business Review prep and the Dubai debrief, a quieter, more personal question surfaces, the one that carries the most weight of all: Would losing this job be the worst thing that's ever happened to me? Honestly? Probably not. And yet the thought of it feels unbearable. Why?
The Psychological Sandwich
Senior executives today are caught in what might be called a psychological sandwich, compressed from both sides at once, with little room to breathe in between.
From above comes structural pressure: geopolitical volatility that reshapes supply chains, market access, and investor appetite without warning. AI models are not merely automating tasks but actively re-engineering the logic of what organizations need and who needs to do it. Boards are demanding efficiency gains measured not in years but in quarters, and increasingly in weeks. The rules of the game are being rewritten mid-match, and the referee is an algorithm.
From below comes the human pressure: teams who are frightened and looking upward for signals of safety. Direct reports who read every micro-expression for clues. Stakeholders who need confidence even when confidence feels like a performance. The executive is expected to radiate certainty from a position of profound uncertainty, which, when you consider it plainly, is an almost impossible ask.
Caught between those forces, the internal erosion begins. It doesn't announce itself. It accumulates. The 'last time' questions are its symptom, the mind scanning the horizon not out of curiosity but out of dread. And beneath the dread lies the real threat: the loss not merely of a role but of identity, purpose, financial stability, and social standing. For many executives, the job and the self have been so thoroughly fused over decades that the prospect of separation feels existential, because, functionally, it is.
This is not a weakness. This is what happens when high-performing human beings operate under sustained, compounding pressure without adequate internal resources to process it. The weight grows week by week, not because the executive is getting weaker, but because the environment keeps adding to it.
So, what do you do with it? You cannot outperform your way out of existential anxiety. You cannot strategy-deck your way to self-worth. What you can do, what, in fact, is required, is to engage with the right questions.
Three Questions to Reclaim the Weight
These are not questions with neat answers. They are questions designed to disrupt the loop, to interrupt the automatic cycle of anxiety and avoidance that keeps executives trapped in the weight of 'what if'. Each one has a specific intent.
Q1 "If this role ended tomorrow, what would remain of me?"
My Intent: This question prompts a rare separation between an executive's identity and their role. High performers often unconsciously tie their self-worth to their position, team, or title. When threatened, the fear isn't losing a job but losing self-identity. Asking what remains without the role helps executives rediscover skills, values, and relationships independent of organizational titles. This isn't about comfort but diagnosis, often revealing surprising and richer insights. The realization that the role is merely a vehicle, not the destination, shifts the weight of self-perception.
Q2 "What am I protecting, and what is it actually costing me?"
My Intent: Fear of loss of status, income, or influence drives behaviors that hinder executives under pressure: defensive posturing, over-controlling teams, and avoiding bold decisions due to risk. This question prompts executives to identify what they're trying to protect and the cost of that protection. Often, protecting their position costs more than losing it. Spending energy managing perception and playing it safe degrades performance and well-being. Recognizing this protection helps dissolve it, enabling leadership that is clear, courageous, and not hostage to survival needs.
Q3 "What would I do differently in the next 90 days if I knew this chapter was ending?"
My Intent: This isn't about resignation, but about liberation, aimed at bypassing uncertainty and helping leaders reconnect with their core values, what they've postponed, and their leadership identity beyond restructuring plans. The best leaders in volatile times act from values, not outcomes, with generosity, not self-protection. They make necessary, even tough, decisions because they aren't driven by fear. This question doesn't eliminate uncertainty but repositions leaders relative to it, distinguishing those burdened by 'last times' from those quietly shaping the future.
The Weight Is Information
The 'last time' questions are not the enemy. They are data. They tell you something important about where you have placed your identity, what you have fused your worth to, and the gap between the leader you are performing as and the leader you want to be.
The environment will not slow down. AI will not pause its disruption out of professional courtesy. Geopolitics will not wait for the next planning cycle. The question is not whether the rules will keep changing. They will. The question is whether you will face that reality from a position of clarity or from one of quiet, accumulated dread.
The heaviest thing an executive carries is not the risk of restructuring. It is the unexamined question of who they are without the role. Answer that, and everything else becomes manageable.
The plane levels out above the clouds. Dubai is gone. The next city is waiting. And for the first time in months, you feel not certain, but strangely ready.
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