When I was recruiting for on-site roles, there were a few questions that always stood out to me in interviews. Questions about culture, company DNA, or career paths.
I appreciated them. At the time, they felt like a signal of maturity. The candidate was thinking beyond the role itself and trying to understand the environment they were about to step into.
For on-site hiring, that made sense. Offices carry a lot of invisible context. You pick things up just by being around people. Culture fills in many of the gaps.
So when candidates asked those questions, I took it as a good sign.
When I started recruiting remote engineers, I carried that same assumption with me. Those questions still sounded familiar and important.
But over time, something didn’t add up.
Candidates were asking those types of questions, but they felt rehearsed, as if they came from a checklist or an AI tool that advised how to prepare for an interview.
I noticed there was no real correlation between the candidates who asked what I considered to be the “right” questions and the ones who actually made it through the process, or performed well once hired.
The people who passed consistently were asking very different things.
Engineers with real remote experience tended to skip the abstract questions altogether. Instead, they focused on how work actually happens, where things get stuck, what’s written down, and what isn’t.
They asked about sync versus async.
About documentation.
About how decisions get made when people aren’t online at the same time.
About what “flexibility” actually means in practice.
Engineers who had actually worked remotely weren’t trying to sound smart. They were trying to avoid surprises and understand how work really runs.
Culture still matters, but it shows up through systems: how work is documented, how decisions are made, and how disagreements get resolved when they don’t happen face to face.
At some point, I stopped paying attention to whether a question sounded “good.”
I started paying attention to whether it sounded useful.
That difference changed how I listen in interviews and what I trust as a real signal.
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