IT planning works when it is a boring quarterly meeting.
The companies that do this well don't run an annual offsite or buy a slide deck once a year. They have a 90-minute meeting every quarter where the same five people review the same roadmap, decide what shipped, and pick what's next. Everything else is consequence. The discipline is unglamorous on purpose: small, regular decisions compound into a stable technology base, while big once-a-year bets tend to age badly.
We bring the technology view: what's stable, what's risky, what's getting expensive, and what's quietly approaching end of life. You bring the business view: what you're growing into, what you're shutting down, where you're hiring, and what auditors are asking for. The roadmap is what's left after both views meet, and a good chunk of its value is the items it tells you not to do, or not to do yet.
This view also makes the rest of your IT spending make sense. The roadmap sets the priorities that your day-to-day operations execute against, decides where security investment goes first, and keeps the largest line items, often Microsoft 365 and infrastructure, from drifting. Strategy without operations is a wish list; operations without strategy is just reacting forever.
"The roadmap line that helped most was the one that said 'do not do this in Q3.' That kind of advice is rare."