The Yearly IT Checkup: A Season-by-Season Checklist for Business Owners

Technology problems rarely arrive out of nowhere. The laptop that dies in July was slow in March. The former employee who still had access in October left in May. A yearly rhythm of short checkups catches these while they're cheap to fix. Here is the one we recommend, spread across the seasons so no single month is a big project. This is the same rhythm we follow with our managed IT clients.

Every month, in ten minutes

• Confirm updates installed on every computer, and that last night's backup succeeded.
• Glance at who joined and who left, and make sure accounts match.
• Read any security alerts your IT provider flagged, and close the loop on each.

Winter: January to March

• Review every account: who has access to what, and who has admin rights. Remove anything that doesn't belong.
• Check that multi-factor sign-in is on for everyone. New accounts are the ones that slip.
• Clean up passwords: move shared and reused passwords into a password manager.
• Warn the team about tax-season scams, especially whoever handles payroll and W-2s.
• Fix the small daily annoyances that slow people down: slow logins, a flaky printer, a shared drive nobody can find. Small fixes add up to hours a week.

Spring: April to June

• Test a backup restore. Pick a real file or folder and bring it back. This is the only proof a backup works.
• Clear out old files, unused apps and accounts for services you stopped using.
• Check the age of every computer. Plan to replace anything past four to five years, or that can't run the current version of Windows.
• Get ready for seasonal staff: accounts, devices and access set up before their first day, and a plan to turn it all off when they leave.

Summer: July to September

• Do a midyear reality check: what changed since January? New software, new people, new locations, new vendors with access to your systems.
• Run a short security training or phishing exercise before vacation season.
• Check that battery backups and surge protection work on your network equipment and servers. Summer storms are hard on equipment.
• Before anyone leaves for vacation, agree on who covers what, and on the rule that payment details don't change while key people are away.

Fall: October to December

• Build next year's IT budget: hardware replacements spread across the quarters, renewals, and any projects.
• Review software subscriptions and licenses. Cancel what nobody uses.
• Check your cyber insurance questionnaire against reality before renewal. Every "yes" should be true.
• Walk through your incident response plan with the people named in it.

New hires and leavers, all year

The first week is where small IT mistakes become habits. A new hire who waits two days for an account starts by borrowing someone else's password. Have accounts, a set-up computer and the right access ready on day one, along with a ten-minute security introduction. When someone leaves, turn off every account, license and shared password that same day.

Signs you're due for more than a checkup

• Computers take minutes to start, and people keep restarting them.
• The same problems come back every few weeks.
• Nobody is sure the backups work, or when they were last tested.
• One person holds all the passwords and knowledge.
• You can't answer your insurer's security questions with confidence.

If two or more of those sound familiar, it's worth a conversation. If you'd like a second set of eyes, we'll walk through this checklist with you.