It's been a minute, right? A lot has happened in the last couple of years, both in the world and at a personal level. AI is everywhere now, hell, my team is building AI at scale 😄 I was considering whether to use AI at least to clean up or polish this blog post and I decided not to use it. These days I'm much preferring that personal touch in writing, not everything you read needs to sound like an English class, amirite?

Turns out I've been doing a lot of interviews lately and that means speaking to a lot of candidates. One of the things I've started doing is doubling down on the behavioral interview for candidates, especially for more senior roles. Whereas before I was treating it more like a pass/fail type of interview, today I've structured it in such a way that I extract a lot of signal from the conversation. How I do this is a topic for another time maybe, but today I want to tell you about something else, something that I realized over the past year or so.

So here's the thing. I ask all candidates variations on the same two ideas:

Tell me about yourself. Tell me about your most exciting work in the past year.

Everyone expects these. Bread and butter. But when I reviewed my notes, most answers were… fine. Too normal. Not wrong—just unconvincing about why I should hire this person.

Let me give you an example. I was hiring senior+ engineers to bootstrap a strategic initiative. I wanted people who were hungry, had strong judgment, and showed growth. A recommended tech lead from a big tech company came through—great promo history, pretty strong in the technical rounds. In our chat, he gave textbook answers. His “most challenging” story was a complex migration with cross-team alignment. Another high-stakes project, similar arc. Competent. But nothing about learnings turned into systems, no big bets, no initiative outside the assigned role, no creative problem-solving that changed the trajectory. For a standard senior role on a steady team? Solid. For what I needed? Not enough. I passed.

Great senior-level interview stories don’t just recap tasks—they show how you changed the trajectory. Set the stakes in concrete terms (what was on the line, for whom), then name the hard choice you faced and the options you weighed. Describe the specific calls you made, how you created momentum across teams, and the one or two creative moves that unlocked progress. Tie it to outcomes that matter—users, reliability, revenue, risk—with evidence where you have it. Close with what you learned and how you turned it into something reusable (a checklist, practice, guardrail) so the impact lasts beyond the project. If others later reused your approach, say so. That’s the difference between “I shipped” and “I raised the bar.”

If you’re interviewing for senior+ roles, remember this: your stories must signal more than experience. At top companies, you’re screened for judgment, initiative, innovation, and growth. You can usually see this in the JD, even if it’s buried under generic text.