Ask Work — hard questions, short answers

100+ hard questions about work and tech-at-work — digital skills, balanced AI, future of work, fun, and retro office. Tip of the hat to Jack Schofield Ask.

Q. Our CEO says we’re “AI-first”. Our backlog says we’re ticket-first. Which do I believe?

Believe the backlog. Strategy is a speech. Work is a queue. If models aren’t in the critical path of how tickets close, you’re AI-adjacent — which is fine, just stop embroidering cushions about it.

Q. Should I put “prompt engineering” on my CV in 2026?

Only if you can explain evaluation, failure modes, and when not to use the model. Otherwise it’s like listing “Google Search” under skills. Everyone can type. Few can judge.

Q. Hybrid policy: three days in office. Nobody’s there on Friday. Enforce or surrender?

Decide what the office is for. If it’s collaboration theatre, Friday emptiness is data — redesign the days that matter. If it’s control cosplay, enforcement will “work” and retention won’t. Pick a purpose before you pick a badge swipe.

Q. My agent writes better first drafts than I do. Am I cooked?

You’re cooked if your value was first drafts. You’re promoted if your value is taste, risk, and the sentence that says “we’re not shipping that”. History is littered with tools that embarrassed craftsmen into becoming editors. Annoying. Survivable.

Q. We banned ChatGPT, then bought Copilot. Staff just use both. Lecture them?

Lecture the policy. Shadow IT is a requirements document written in guilt. Publish an approved path that is faster than the forbidden one, or enjoy your double life.

Q. Honest answer: will my kids have jobs?

Yes. Different ones. Worse titles, better leverage — if we teach judgement alongside tools. The unforgivable failure isn’t automation. It’s raising a generation that can’t tell when the machine is wrong.