Why New Leaders Avoid Asking the Obvious
It usually hits you before you’ve even finished updating your email signature — that odd, slightly metallic pressure that creeps in the moment you “become” a leader.
Suddenly you’re meant to have answers lined up like a supermarket queue. Encyclopaedic, evergreen, ready-to-deploy solutions for anything from API design to why Dave looks miserable in the stand-up.
It makes perfect sense. When you’ve spent years as an IC, the whole economy of your worth is built on knowing stuff — or at least wrangling it convincingly. Fix the bug, untangle the knot, be the one who can take a Friday-afternoon panic and turn it into a Monday-morning commit. That muscle memory doesn’t disappear just because someone hands you a different badge.
But leadership has this sneaky way of rewriting the rules when you’re not looking. It turns the whole game sideways. It’s no longer about being the sharpest tool in the box but finding ways to help other sharpen their tools. A leader’s power — their actual, proper leverage — shows up in the questions they lob into the room, not the answers they hoard.
And yet, simple questions terrify people.
“Won’t I sound dim?”
“Isn’t that too basic?”
“Shouldn’t I… already know this?”
We’re so conditioned to fake omniscience that anything plain risks puncturing the balloon. Complexity sounds clever; simplicity sounds, well, naked. And risky. And like you might reveal that you’re still human, which is apparently some sort of crime in certain companies.
But simple questions are dangerous for a better reason: they cut straight through the theatre. No velvet curtains, no polite throat-clearing, just a clean line into whatever’s actually going on. Which is why they land with such force.
I remember one meeting — tense, stuffy, the sort of architectural debate where half the energy goes into Excalidraw diagrams and the other half into territorial vibes. Everyone talking past each other. I sat there, sipping lukewarm coffee, whilst wondering which market stall to get lunch from. Eventually, I said:
“What problem are we actually trying to solve?”
Silence. It felt almost too obvious to speak aloud. But it rewound the entire room to the beginning. It turned out the two loudest factions were optimising for completely different outcomes.
Ten minutes later, the whole thing unclenched. Decision made. Shoulders dropped. Someone even laughed. It wasn’t my brilliance (which, frankly, was dedicated to finding the ideal lunch baguette). It was the question they hadn’t thought to ask because they were too busy performing expertise for one another.
Across the rather different places I’ve worked, it’s always the same pattern: the leaders who impress are rarely the ones with the grand monologues. They simply ask the candid, direct question at precisely the moment the room needs it.
The higher you climb, the simpler your most powerful questions become. Not because you know less, but because you’re finally confident enough to stop pretending you know everything. Those questions have a way of stripping out the story everyone’s clinging to and revealing the thing itself, sitting quietly in the middle of the table.
Leadership, when you stop playing oracle, gets a lot lighter. You don’t need a brain like the British Library. You need curiosity, a bit of presence, and the nerve to ask the question everyone’s been dancing awkwardly around.
More often than not, it’s the simplest question — almost embarrassingly simple — that opens the door.