Driver, Not Doer

My teams are fully remote. There is no one looking over anyone's shoulder, and I do not want there to be. That model only works with people who take initiative by default, set their own direction inside a goal, and close the loop without being chased.

Because these are senior positions, I also need someone who can explain the why and the how, not just the what. "I built the payments service" tells me nothing. I want to hear the trade-offs they weighed, why they chose one approach over another, what they would do differently, and how they reason about a system they have never seen before.

That is what separates a senior engineer from a mid-level one with a longer resume. Both of those candidates defaulted to listing accomplishments rather than reasoning through them, and when I pushed on the why, the depth was not there.

• Evidence of true ownership. They drove a project or feature from problem to production, not just contributed to one that someone else was steering.
• A track record of thriving with minimal direction. Autonomous or distributed settings, where nobody was assigning the next step.
• Depth of reasoning. Ask them to explain a past decision and why, then see whether they go beyond the what. Push twice. The second push is where the answer gets honest.
• Scope and impact they personally drove, not team accomplishments they were adjacent to.
• Willingness to disagree with me in the interview. If a candidate cannot push back on a technical premise during a conversation, they will not push back on a bad architectural call in month four.

I would rather see two candidates who clearly clear that bar than ten who match the keyword list.