May 1, 2025

Side-Skilling

When I was a PM at CustomInk we were growing fast, which meant hitting new bottlenecks every few months or so.

At one point our product teams were sharing UX resources, and design wasn’t able to keep up with development. Rather than slow down our team I started pushing pixels, leaning heavily on writing from Jared Spool and Steve Krug to crystalize and make explicit knowledge of what had been mostly been intuition.

Later, as data requests starting queuing up for weeks, I complained to my manager. He said I could probably pick up SQL in a week and grabbed a small reference book of his shelf. He was right, and our team was off to the races again.

Each sidestep kept the team moving and added a new tool to my belt. That pattern still matters, but the reasons have changed.

Side-skilling vs Up-skilling

Up-skilling digs deeper into your current lane. A frontend engineer becomes proficient at animation and motion design. An ops manager goes deep on Six Sigma. A general ledger accountant masters driver-based forecasting. Up-skilling sharpens a single blade.

Side-skilling extends outward, picking up neighbouring competencies that let you diagnose and unblock the whole system. It turns the blade into a multi-tool.

Why it matters now more than ever

LLMs can cover the first draft of almost any specialised task. What’s left is judgment: knowing which outputs to trust, which follow-ups to run, when to switch perspective. Good judgment requires a view across functions, not just down one lane.

Why it’s easier than ever

The learning curve for a new domain has collapsed. You can pair with an LLM on SQL, ask it to critique a Figma mock, or have it explain logistics KPIs, then test what it shows you. Curiosity plus a few focused sessions often gets you to “good enough to unblock the team.”

Working practice

1. Identify the nearest constraint outside your role.
2. Learn the minimum skill to relieve that pressure.
3. Repeat as constraints move.

Specialisation anchors your craft; side-skilling broadens your map of the system. Both are becoming table-stakes.