The Question I Keep Getting Wrong
I’ve been asking that question for years now — including of myself. I’m still working on the answer.
Three years ago, she arrived for our second session with the prepared version already running.
I could tell before I said anything. She sat down, arranged her bag, and looked at me with the particular alertness of someone who’d done their homework. She’d thought about what I would ask. She came ready.
“What do you want?” I said.
She answered immediately — clearly, without hesitation. It was a good answer, organized, plausible. I wrote it down. We spent forty minutes building from it: a values map, a time she’d felt genuinely engaged in work, the things she said she wouldn’t compromise on.
By the end, she looked politely exhausted. She was trying hard. She was just far from something.
The answer she gave me was real. She’d thought about it for weeks before arriving. But it had become its own kind of armor — what she could afford to want, out loud, in front of someone watching.
What she actually wanted was different. I found out later, when she mentioned it in an aside: what the work would have to feel like for her to believe it was genuinely hers. That sentence surfaced in the last ten minutes of our fourteenth session. Six months in, and it had been waiting the whole time.
“What do you want?” is not a neutral question.
It asks the person to have already arrived somewhere they usually haven’t. Made peace with how things went. Become ready to reach forward. The people who come to me — through layoffs, role eliminations, the specific disorientation of watching work built over fifteen years become adjacent to automation — are often still inside the question of whether what happened was failure or just a place they didn’t plan to visit.
Asking what they want before that’s settled is asking them to build from a floor that hasn’t been laid.
Wanting is a vulnerable act. It requires believing the want is legitimate before it arrives. If what you want turns out to be wrong — misguided, too large, somehow naive — you’ve failed in a way that’s visible. So people, before they can want something clearly, need to believe it’s safe to want it.
That safety is something specific: a belief that the current situation is not a verdict. That arriving here — over-prepared, three months out of a role they’d already outgrown — is a moment inside something longer, not the conclusion of it.
For years I treated “What do you want?” as the entry point. What I was often doing, in those sessions, was asking someone to perform wanting — to produce a coherent desire — before they’d had permission to settle.
Clarity is the easier problem. Permission takes longer.
Permission, in practice, has a recognizable shape: it’s the moment someone stops explaining how reasonable they’ve been about what happened — the measured recounting, the fair accounting — and says something unguarded instead. A sentence that didn’t go through review first. An answer they couldn’t have given to the same question an hour earlier.
I’ve watched clients shift from a rehearsed version of themselves to something truer in twenty minutes. The questions before that moment had been doing the real work — making it safe enough to stop performing clarity they didn’t have.
The question I lead with now is something like: “What did you come in having already half-decided?”
In a session it’s usually simpler — “What’s the thing you’ve almost said?” or “What did you half-decide on the walk here?” What I’m pointing at: the real material is usually already present, in formed shape, before the person sits down. They’ve been carrying it. My first question has shifted from what do you want to something closer to what are you protecting from yourself.
This is a harder question to ask, in a specific way: it requires trusting that the answer is already in the room. The work has become about making it safe enough for what’s already there to surface.
Three sessions ago, a client was walking me through his situation in careful, organized detail. The precise ordering of someone filling space, keeping the real question at a distance.
He ran out of things to say. A pause settled in the room.
Then: “I think I already know what I want to do. I just don’t know if I’m allowed to want that.”
The question I’d been planning to ask had already answered itself. Once there was room, he arrived without me. He sent an email the next morning. He’d already started looking.
This is simpler than coaching methodology, maybe. Most of the people I work with can reach what they want, once they believe it’s safe to reach for it. What’s harder to find is permission — not from anyone external, not from circumstances or whatever their former manager said on the way out. Whether the person has given it to themselves.
When that shifts, the question I used to lead with tends to answer itself.
That afternoon, after the client had gone, I sat in the consulting room for a while. The geraniums through the window. My notebook open to a blank page.
I wrote the question at the top: What did you come in having already half-decided?
The ink dried. The geraniums again. The sound from the courtyard.
I’ve been asking that question for years now — including of myself. I’m still working on the answer.
— Tiago
This is a newsletter about the inner experience of the AI transition. If this found you at the right moment, share it with someone who might need it.
If you’re new here: I’m Tiago Villares, a career coach based in Lisbon. I’ve spent the last three years working with people navigating career transitions in the age of AI — and writing about what that actually feels like from the inside. My first book, “After the Wave,” is out now.
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