One Question I Ask In Almost Every Mentoring Session

One question I ask in almost every mentoring session:

"Tell me about a recent technical decision you made. What did you consider but decide against?"

The answer tells me exactly where someone is in their growth.

Mid-level engineers describe the solution they picked. They walk me through the implementation, maybe mention it's working well in production.

Senior engineers describe the battlefield. They tell me about the option that would've been faster to build but harder to maintain. The approach that worked great at their last company but didn't fit this team's strengths. The "right" answer they rejected because the timeline didn't support it.

The difference isn't experience or intelligence. It's that seniors have learned to think in tradeoffs instead of solutions.

I've noticed the same pattern shows up everywhere:

When I ask "what's something your team does that you disagree with," mid-level engineers vent. Senior engineers tell me whether they've raised it, what happened, and what they learned about picking battles.

When I ask "when's the last time you were wrong about something technical," mid-level engineers struggle to find an example. Senior engineers have one ready and can tell me how it changed their approach.

Mid-level engineers tell stories while senior engineers share reflections.

If you're trying to make the jump, start noticing the options you're discarding. That's where the growth happens.

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