Put your IT on the same calendar as your business
Most small offices make technology decisions when something breaks or a renewal notice arrives. The result is spending that surprises you, upgrades that land in your busiest week, and tools nobody quite remembers buying. A little planning, done a few times a year, keeps your technology pointed at what the business is actually trying to do.
Start with the business calendar
Mark the weeks your office can’t afford disruption: tax season, renewal periods, year-end close, trial dates, open enrollment. Those are the weeks to avoid migrations, new phone systems and anything else that changes how people work.
Then mark the quieter stretches. That’s when upgrades, training and cleanup belong. When technology work is scheduled around the business, your team notices the improvement instead of the interruption.
Connect every cost to a job
List what you pay for each month: Microsoft 365 licenses, line-of-business software, backup, security tools, phones and internet. Next to each, write the job it does and who uses it.
Anything without a clear job is a question to ask. Paid seats for people who have left, two tools that do the same thing, and features nobody has turned on are common, and they add up quietly.
Plan replacements before they become emergencies
Keep a simple list of every computer, its age and its operating system. A machine that has to be replaced next year is a budget line. A machine that fails in the middle of your busy season is a crisis.
Operating systems have end dates too. Microsoft stopped providing security updates for Windows 10 on October 14, 2025, so any office computer still running it should be on this year’s replacement or upgrade plan.
Know what clients, insurers and regulators will ask
Cyber-insurance applications, client security questionnaires and regulations increasingly ask the same things: Do you require multi-factor authentication? Are backups tested? Is there a written security plan? Having the answers ready is part of running the business, not a separate IT project.
If you prepare tax returns or offer other financial services, the FTC Safeguards Rule likely applies to you and requires a written information security program. Plan for it the way you plan for any other compliance deadline.
Make it a short, regular conversation
Once a quarter, spend 30 minutes on four questions: What slowed the team down? What is changing in the business, such as new hires, a new location or new software? What is getting old? What will it cost over the next 12 months?
Write the answers down and keep a one-page plan. Purple Bunny holds these reviews with clients and turns them into a 12-month technology roadmap and budget. If you’d like a starting point, our free 21-Point Office IT Review shows where your office stands today.