UP Small Business Technology Readiness Checklist

01 //Ownership & Documentation

Your business — not an individual employee or outside vendor — is the registered owner of your domain name and it renews to a company-controlled account.

You have a current, written inventory of the software, cloud services, and hardware your business depends on.

Admin credentials, license keys, and account recovery details are stored somewhere the business can access without any one specific person.

If your current IT support left tomorrow, someone else could get the documentation needed to keep the business running.

02 //Identity & Access

Multi-factor authentication (MFA) is turned on for email, banking, and any system holding customer or financial data.

Nobody shares a single login across multiple staff members for an important system.

You have a written process for removing access the same day someone leaves the business.

Passwords are unique per system and stored in a password manager, not a shared spreadsheet or sticky note.

03 //Endpoint & Security

Every business computer runs current antivirus/endpoint protection and receives security updates automatically.

Personal, unmanaged devices are not used to access core business systems or customer data.

Staff have had phishing awareness training within the last 12 months.

Your Wi-Fi network separates guest traffic from the network your business systems run on.

04 //Microsoft 365 / Data

You know who has admin rights in your Microsoft 365 or Google Workspace tenant, and that list is current.

Shared mailboxes, Teams/SharePoint sites, and shared drives each have a clear owner, not an "everyone has access" default.

You have reviewed which third-party apps are connected to your email or file storage in the last year.

05 //Backup & Restore

Backups run automatically and are stored somewhere separate from your primary systems (a different account, location, or provider).

You have actually tested restoring a file or system from backup — not just confirmed that a backup job ran.

You know how long a full restore would realistically take, and whether that's acceptable for your business.

06 //Onboarding & Offboarding

New hires get a documented, repeatable process for account and equipment setup — not an ad hoc one.

Departing staff have every account, device, and access credential deactivated or returned as part of a checklist, not from memory.

07 //Internet, Phones & Continuity

You know what happens to phone calls and email if your internet connection goes down.

You have a basic written plan for continuing to operate through a multi-hour outage or hardware failure.

08 //Vendors

You have a current list of every vendor with access to your systems or data (IT, payroll, POS, industry software).

You know what each vendor is responsible for securing, and what you are responsible for — in writing, not assumed.

09 //Cyber Insurance

You know whether your business carries cyber insurance, and what security controls the policy requires you to maintain.

You could produce evidence (screenshots, reports, policies) of your current controls if an insurer asked at renewal.

10 //Public AI Use

Staff have written guidance on what business or customer information may not be pasted into public AI tools.

Before enabling an AI assistant connected to your files or email, someone has reviewed what it can actually access.

// How to Use Your Results

This checklist is a prioritization tool, not a pass/fail test, and checking every box does not mean your business is "compliant" or "secure" — no checklist can promise that.

A practical way to use it: count the unchecked items in each section. Sections with the most unchecked items are where risk is currently concentrated, so start there. Treat unchecked items in Identity & Access and Backup & Restore as the highest priority — access failures and untested backups are the two issues most likely to turn a bad day into a bad year.

If you'd rather walk through this with someone instead of self-scoring it, that's what a guided IT assessment is for.

UP Small Business Technology Readiness Checklist

// How to Use Your Results

Want a Second Set of Eyes on This?