Don’t Take Your Laptop

September 23, 2026

From Alex Rosario, OpenNova.

In May, in a team meeting at a company we work with, a technology leader told an engineer heading out for a week: don’t take your laptop. If something breaks, I’ll call you.

He was honest about it. The team wasn’t yet trained to cover that engineer’s work, and a call was still possible. What he wanted was for the team to stop depending on one person’s vacation availability, and he told them why.

His argument wasn’t about rest. It was about careers. If you’re the only one who can do one thing, you’re stuck doing that thing. Holding on to it can feel like job security. His point to the team was that it works against the person holding on. As people get more senior, he said, their value stops being only the code. It becomes architecture, domain knowledge, and the judgment about what can ship and what shouldn’t. That’s hard to grow into while you’re the only one keeping a service running.

I’m not going to tell you we see this everywhere. We saw it clearly once, and it has stuck with us, because it flips the usual framing. Key-person dependency usually gets described as a risk to the company. He described it as a ceiling on the person.

So here’s the test I use, and I’d use it on my own team.

A senior person or a manager leaves for a couple of weeks and things still get done. Not everything, and not perfectly, but the important stuff moves. If the honest answer is that a few things would sit until that person gets back, that isn’t a vacation problem. That’s a dependency the team hasn’t solved yet.

And the runbook doesn’t count. Written down is not the same as covered. Coverage is someone else who can do the job, and the only way to find out is to let them try while the first person is still around to take the call.

We don’t know how this one ends yet. The engineer took the week.

Coming soon: Executive Spotlight. Short conversations with executives, operators and experienced leaders about a decision, a lesson, or a challenge they’re still working through.

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