Year-End IT Planning: Questions to Ask before January

In September, a client forwarded us an annual invoice for a subscription they were locked into by an old provider and asked "is this right?" It wasn't. They were being billed for more than they needed and the cost per unit had gone up, it came out to almost $1000 extra. To add to the frustration, it had to be corrected with the vendor last year.

A year-end IT review is a few hours spent asking that kind of question about everything your business pays for and depends on, in November or December so you can start the new year fresh with a plan.

Why Late in the Year Is a Good Time for an IT Review

• ✓If any of your annual software plans or security subscriptions renew at year-end/beginning, reviewing them now gives you time to drop unused licenses or compare other options.
• ✓If you plan to hire in the new year, equipment ordered in December arrives ready to set up. Equipment ordered the week before a start date may not arrive in time.
• ✓By December you have a full year of invoices and support requests to look back on, which shows what the business actually used and where the problems were.

Questions about Your Hardware

Start with the equipment people use every day.

• ?How old is each computer, and when does its warranty end?
• ?Is every machine on a supported version of Windows? Windows 10 reached end of support in October 2025. Any machine still running it either needs an upgrade or is relying on extended security updates, which are temporary.
• ?Which machines are slow or unreliable enough that people have started working around them?
• ?Is a spare laptop ready if one fails or a new hire starts early?
• ?Are your firewall and wireless access points still receiving security updates?

The goal is a replacement schedule. Replacing a few machines every year is easier on the budget than replacing everything in a pinch when they start failing during a busy time.

If you don't have a hardware inventory yet, a spreadsheet is enough to start. List each device, who uses it, when it was bought, and when its warranty ends. Add printers and network equipment too. They tend to get forgotten until they stop working and a firewall with no new updates is a security problem on top of a hardware problem.

Questions about Software and Subscriptions

Subscriptions are easy to add and easy to forget. Pull the last few months of invoices and company card statements, then ask:

• ?Are any licenses still assigned to people who no longer work here?
• ?When does each annual plan renew, and how much notice does the vendor need before you can reduce seats or cancel?
• ?Are two tools doing the same job? File sharing and video meetings are common places for overlap, especially when different departments picked different tools.
• ?Did anyone buy software on a personal or department card that IT doesn't know about?
• ?Which tools did you pay for all year and barely use? Some of them need training more than they need canceling.

Notice periods deserve their own column. Some annual agreements renew automatically and only let you reduce seats during a short window before the renewal date. Miss that window and you pay for another year of licenses nobody uses.

Write down what you find, along with each renewal date. That list becomes most of your software budget.

Questions about Security and Access

Access piles up over a year. People change roles, and a contractor or vendor keeps access long after the work is done because nobody remembered to remove it.

• ?Does everyone who can get into your systems still need to? Former employees and finished contractors are the first place to look. Our offboarding checklist covers what to remove.
• ?Is anyone sharing a login? With a shared account, you can't tell who did what. We covered that in “One Login For Five People? That's A Problem.”
• ?Have your backups been restore-tested this year? A backup job that reports success shows the job ran. A test restore shows you can get the data back.
• ?Is multifactor authentication (MFA) turned on for every account that supports it, including admin accounts and remote access?
• ?Who controls your domain name, and when does it renew? If the answer is "a web designer we used four years ago," fix that before the renewal date.
• ?When does your cyber insurance renew? Applications ask detailed questions about MFA and backups, and those are easier to answer after a review than in the middle of one.

For firms that handle regulated client data, like CPAs and medical practices, this section overlaps with compliance obligations. Documenting the review now gives you a record to point to if a regulator or insurer asks.

Questions about Your IT Support

Look back at the year's support requests, whether they went to an outside provider or to the person in the office who knows computers.

• ?Which problems came up more than once? Repeat issues usually point to something that should be fixed properly instead of patched again.
• ?Is your setup documented anywhere other than one person's memory?
• ?What does your support agreement cover, and what gets billed separately? Projects and after-hours work are the usual surprises.
• ?If your IT person or provider were unavailable for a week, would anyone know where the vendor contacts and admin accounts are recorded?

Questions about Next Year's Plans

IT planning works best when it starts from the business plan. Talk to whoever runs each department and ask what's changing.

• ?Are you hiring? When? Each new person needs equipment and licenses ordered ahead of their start date.
• ?Is an office move or a new location on the calendar? Internet installation usually needs to be scheduled well before move-in day.
• ?Is a department planning to adopt new software? New tools will have setup and training work beyond the license cost.
• ?Are any client contracts or regulations changing in a way that affects how you handle data?

Turning the Answers into a Budget

Once you have the answers, most of next year's IT budget is already sketched out. The hardware on your replacement list, the subscriptions you're keeping, the projects departments asked for, and a reserve for things that break all become line items.

A January Plan, Week by Week

Decisions made in December still need someone to carry them out. A simple January schedule keeps them from slipping.

Year-End IT Checklist

None of these items takes long on its own. Spread across a few afternoons in November and December, the review means January starts with decisions already made and orders already placed.