Year-End IT Checklist For 2025

A Year-End IT Checklist for Small Business Owners

Like many of you, our normal operations tend to slow down for us this time of year, leaving space to reflect on what’s working, and plan for what’s ahead. Here are just a few of the tech cleanup and planning items we are working through over the holidays:

Email Setup & Security

Most of us are now using multiple channels to communicate and coordinate with our clients and partners, but email remains one of the most important ones in our business. A quick check on these items can help to keep you out of trouble:

• Inbox Limits: If you are on a modern email platform, chances are good you have a lot of space to work with. But if you are on an older platform or get a bunch of email with big attachments, you need to stay on top of the clutter.
• Spam Filter Settings: These settings are tricky. Make them too loose and the hacker-attack emails will slip through. Make them too tight and an important email could be flagged and dropped into the spam folder abyss.
• Antivirus Protections: The antivirus tools are often your last line of defense against a ransomware attack. In a perfect world you should have at least two antivirus checks for each email that you receive, so make sure your antivirus tools are paid up and active.

Revisiting Cybersecurity Protections

I’ve already mentioned cybersecurity for our emails, but the threats evolve continuously and the attacks can come in from many other channels besides email. The biggest challenge is that cybersecurity is very easy to ignore, at least until there’s a problem. Be proactive:

• Password Management: There’s no one-size-fits-all solution to password management. I wrote a blog post about this recently, and the main point is to think about what you are doing and make sure it still makes sense for your business.
• Multi Factor Authentication: MFA is still one of the most effective tools in the toolkit to keep hackers at bay. Nobody likes doing it, but it needs to be enabled until we find an easier way to keep things safe.
• Unauthorized Apps: If you let your team install whatever they want to install on their PCs and phones, and then let them connect those tools to your business, you almost certainly have a cybersecurity risk.

Audit Backups and Syncs

The starting point here is to make sure you understand the difference between data sync services and backups. Both are great tools to have, but they serve two very different roles, so you need to be sure they are working properly.

• Sync Services: OneDrive and Google Drive are the two most popular sync services, and they continue to get better every year. Sync services do a great job at keeping our information available to us, but the one area where they come up short is making it easy to recover from a disaster like a fire, flood, or cyberattack.
• Backup Your Stuff: Having a separate, complete copy of every computer and server environment is the best insurance policy you can have. All computers fail eventually, and a good backup solution can have you back up and running quickly if things get crazy.

Prepare for Power or Internet Outages

Winter and summer are the seasons when power grids are stretched thin, so it’s a good idea to make sure you are ready for the moment when the power goes out.

• UPS Systems: Test the battery backups for the uninterruptable power supplies that support your computers, routers, servers, phones, all of them.
• Internet Failover Plan: Most offices grind to a halt when the internet goes out, so having a plan to keep going is essential. A small office might be able to get away with using a cellular hotspot in a pinch, but if you have a bigger team or downtime isn’t an option for your business, it may make sense to invest in a second, backup internet provider.
• Remote Work Capability: If the primary office has a long-term issue with power, internet, safety, or some other problem that forces everyone to work from home, make sure that you have everything set up in advance to keep the business going until you can get the main office back on track.

Implement AI. Carefully.

If you are in a professional-services business and you haven’t already started dabbling with AI, you are probably falling behind your competition. That being said, AI is still very much in its infancy, so it’s important not to get ahead of where the technology is.

You don’t need to overhaul your business to begin benefiting from AI. Consider:

• Pick An AI Anchor: Our business uses the Microsoft productivity tools, so we are starting to train Copilot on our business so that it can add real value in 2026. If you are using Google Workspace, then Gemini may be the best tool to start with.
• Augment As You Go: We still find that ChatGPT to be better general knowledge tool than Copilot, although my guess is that reality will slowly shift as Copilot gets more familiar with our business.
• Get Specific: We are also training a hyper-specific AI tool on our IT support operations, with the intention of having the tool begin to augment our human team in customer support sometime in the future.
• Stick To Baby Steps: We find that the AI tools that we are using right now are routinely overconfident in the self-assessment of their knowledge and skills, so we do not let them do anything unsupervised. It’s tempting to think that these tools are going to make our lives easier, and they probably will eventually, but for now you are better off thinking of them as a junior-level assistant that needs constant supervision and training.

Pulling It All Together

Taking the time to tighten up your IT systems and to think carefully about how you will use technology in 2026 is a good use of time. If you’re not sure where to start (or want a second opinion), feel free to schedule a conversation with me. I’m always happy to learn more about you and your business, and to help you step into the new year with confidence.