A CTO I know had two finalists for a Head of Engineering role.
Candidate A: ten years at a well-known enterprise company. Impressive CV. Every box ticked.
Candidate B: smaller teams, a two-year career gap, but sharp in every conversation. Asked questions in the technical round that nobody else thought to ask.
The board leaned toward A. Fair enough. Clean references, and nobody could say they hadn’t done the checks.
They hired A.
Six months later, the CTO called me.
Candidate A had spent his first three months building process. Documentation. Governance frameworks. Team rituals.
The team was fourteen people trying to ship a product under serious delivery pressure. They didn’t need more process. They needed someone who could make fast decisions and keep engineers unblocked.
A had never operated without a structure already in place. He genuinely didn’t know he couldn’t. And nobody tested for it during the interview.
Candidate B, they checked, went to a competitor. Helped them ship three major product updates in his first quarter.
The CTO didn’t make a bad hire. He made a hire that looked right on paper and cost him most of a year of delivery.
An interview rewards people who explain well. They’re easy to like, so nobody looks further. And “we” hides a lot.
So when someone tells me “we delivered the migration”, I want to know what they carried. What decision was theirs when there wasn’t an obvious answer? What went wrong? What did they personally have to fix?
I’m not after the best storyteller. I’m after who carried it.
