AI readiness checklist: 15 questions to answer before you buy anything.

How to use this checklist

Go through the fifteen questions and tick each one that's true today. Don't overthink it. A rough yes counts. Your score updates as you go, and nothing you tick is saved or sent anywhere.

The work

• Someone does the same task every week. Following up on quotes, entering bills, answering the same customer questions.
• You can say roughly how many hours it takes. Across everyone involved, per week or per month.
• You know what it costs when it slips. A lost job, a late payment, an unhappy customer, a weekend spent catching up.

The data

• The work lives somewhere digital. Email, a spreadsheet, QuickBooks, a scheduling or field-service app. Not only paper or memory.
• Your key lists are written down. Prices, services, the questions customers ask most, the answers you give.
• You can export your records. Most business software can download a spreadsheet of jobs, customers or transactions.

The tools

• You've checked what your software already does. Many platforms now include AI features. See what's built into ServiceTitan, Jobber and QuickBooks.
• Your business owns its accounts. Email, files and software are in the business's name, not an employee's personal account.
• You can give someone access without sharing a password. For example, adding an accountant user in QuickBooks or sharing a folder.

The people

• One person can own it. Someone who'd approve a morning batch of drafts or check a weekly list.
• That person has ten minutes a day for it. Automations stall when nobody reviews their output.
• Your team is open to trying it. Curious beats skeptical, but skeptical and willing is fine.

The rules

• You know which AI accounts your team uses today. And they're business accounts, not personal ones. See Is ChatGPT safe for company data?
• You know what can't go into an AI tool. Card numbers, Social Security numbers, health details, and anything under a confidentiality agreement.
• If you text customers, you have their consent on file. Or you don't text customers at all.

What your score means

• 12 to 15: You're ready to automate something. Pick the task from "The work" that costs the most hours and start there.
• 7 to 11: You're close. The gaps are usually in "The data" or "The rules," and fixing them is useful even without AI: a written price list, business-owned accounts, a one-page AI policy.
• 0 to 6: Start with the basics. Choose one business AI plan, move your team onto it, and write down the lists that live in your head. Come back in a month.

Any score is a fine place to start a conversation. The first call with us is free, and these are the same questions we'd ask. If there's a fit, the $999 AI Assessment turns your answers into a ranked plan with estimated hours saved. For ideas on what to automate first, see 24 tasks a small business can automate with AI.