"When ‘I don’t know what to do’ is a step forward"

“I don’t know what to do.”

That was the refrain in my 1:1 with a principal engineer.
They weren’t confused about a system or a bug. They were confused about themselves.

Their instinct told them to get back into the code. That’s what had always worked before. But it didn’t feel right either. We agreed, that’s what a senior or mid-level engineer does. Their new role was something different. Less prescriptive. More impactful.
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Here’s the thing: when we’re unsure, we retreat to the familiar. For a software engineer, that often means coding. It feels safe, productive, measurable. But at higher levels, the value isn’t in doing the work directly, it’s in shaping the conditions for others to do it well.

That transition was disorienting. For them, “not knowing” felt like failure. But it wasn’t. It was a sign they’d crossed into new territory, the place where impact comes not from what they built, but from what they made possible.

The instinct to go back was natural. The challenge was helping them to sit in that space long enough to move forward.

Until next time,
Dermot
The Messy Middle.

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