Planning for 2026: Why the Holiday Season is the Best Time to Think About AI and Technology Strategy
By the third week of December the phone mostly stops. Clients are away, nobody is booking anything, and the inbox fills up with out-of-office replies. For a lot of New Zealand businesses the work doesn't properly start again until the middle of January.
I used to treat that stretch as dead time. Now I think it's the most useful three weeks of the year, and not because I spend them working. It's the only point in the calendar where you can think about your own business without something else pulling at you.
You don't get that in February. From then until November you're delivering, and the thinking gets squeezed into whatever gaps are left. Which is why, for most people, it never happens at all.
What the quiet is actually good for
Not a strategy document. If you come out of January holding a twelve-month technology roadmap, you've probably written fiction.
What it's good for is noticing. You've just finished a year, so you know which jobs ate your time, which ones your team complained about, and where things fell over. That knowledge is sharp in December and mostly gone by March.
Write it down while you still have it. An honest list of what annoyed you this year is a better starting point for technology planning than any framework I could hand you.
Start with where you actually are
Before you decide what to buy, work out what's already happening. Ask your people whether they use AI at work, what for, and whether they check what it gives them. Ask in a way that can't get anyone in trouble, or you'll get the answer you want rather than the one that's true.
You'll find more than you expect. People are already using these tools, and most of them haven't mentioned it because nobody told them they could.
That's your baseline. Not a maturity score, just an honest picture of what is already going on in your business.
Pick one thing, not a transformation
The temptation in January is to plan something big, and it's worth resisting. Pick one workflow instead. Something that runs regularly, that more than one person touches, and that nobody in the room will defend. Month-end reporting. Quoting. Onboarding a new starter.
One workflow done properly will teach you more about what these tools can do in your business than a year of reading about them. It also gives you something concrete to point at when someone asks what you've actually done, which matters more than it probably should.
Decide now what you'll measure
This is the part everyone skips, and it's the part that decides whether next December feels any different from this one.
Before you change anything, write down how long the job takes today and who does it. A rough number is fine, and a rough number you wrote down in January beats a precise one you estimated in June. Without it you end up arguing about whether things feel better, and that argument has no end.
If you can't say what you'd measure, you're not ready to start. Finding that out in January is cheap.
What to carry into February
Three things. The honest picture of what your team is already doing, the one workflow you've chosen, and the number you wrote down before you touched anything.
That fits on a single page, which is the point of it. The plans that fail are the ones that need another quiet week to get going, and you won't get another quiet week until next December.
