Start with how small businesses actually get hurt. Most incidents begin with a stolen password, a fake invoice or a phishing link, and the worst ones end with ransomware on every machine and the backups encrypted too. That points to a short list of controls that matter most: multi-factor login on email and remote access, protection on every laptop and server, filtering for mail, and backups that an attacker can't reach.
Next, decide who will watch the alerts. This question matters more than any feature. A good EDR tool raises alerts, and someone has to read them, often at night or on a weekend. If you have no security staff, look at tools with a managed option, where the vendor's analysts review detections and act on them, or work with a managed service provider that runs the tools for you. A powerful product nobody looks at protects less than a simpler one that someone checks every day.
Count what you already own. Microsoft 365 Business Premium includes Defender for Business, Defender for Office 365 Plan 1, Entra ID P1 and Intune. Google Workspace has its own mail filtering and login controls. Turn on and tune what you are already paying for before you add another agent or console, then buy to fill the gaps.
Be specific about the AI. In this field it usually means one of a few things: models that judge whether a file or process is malicious, models that learn normal email or login behavior and flag what breaks the pattern, and assistants that summarize alerts or answer questions in plain language. Ask the vendor which of these applies, what data the model sees, whether your data trains it, and how often it flags something harmless.
Check how the pieces fit together. Each agent you install uses memory and needs updates, and two antivirus products on one machine can fight each other. Ask whether a new tool replaces something you run today or sits beside it, and whether it can send alerts to the place your team or MSP already looks.
Test your backups before you need them. Keep at least one copy offline or immutable, so it cannot be deleted from a stolen admin account, and restore a full machine on a schedule. Backup is the tool that decides whether a ransomware attack is a bad week or the end of the business.
Finally, plan for people. Awareness training and a password manager only work if staff use them, so pick tools that are easy for non-technical people, explain why they are being added, and make it simple and safe to report a mistake.