The Small Business
AI Readiness Checklist.

Map the work your team actually does.

To build the picture:

• List every recurring task by role — intake, drafting, reporting, follow-ups.
• Note frequency and estimated hours per week for each.
• Flag the ones that repeat daily and require low judgment.

Pick three workflows worth automating.

To prioritize what's worth it:

• Rank by hours spent × repetition × low judgment required.
• Start with three — not thirty. Ruthless focus beats ambition.
• Common wins: document drafting, client intake, status updates.

Baseline your numbers first.

To make ROI measurable:

• Capture today's hours per task, response times, cost per client.
• Save one timestamped snapshot you can diff against in 90 days.
• Without a baseline, any "it feels faster" claim is just vibes.

Discuss concerns openly with your team.

To address change head-on:

• Ask where people feel threatened, curious, or skeptical.
• Be explicit: AI augments this work; we're not cutting headcount to do it.
• Invite one "AI skeptic" into the pilot — they make the best stress-testers.

Get your data out of people's heads.

To give AI real context:

• Centralize SOPs, templates, FAQs, and client info in one reachable place.
• Kill the "only Sarah knows" single points of failure.
• AI is only as useful as the context you can feed it.

Clean up your customer & contact records.

To stop garbage-in, garbage-out:

• Deduplicate your CRM; standardize fields; archive the dead.
• Fix the 10 fields your team actually queries — not all 80.
• This is the single biggest readiness lever for most SMBs.

Write a one-page AI use policy.

To use AI responsibly:

• List approved tools; specify what data is off-limits (PII, client confidential).
• Require human review before any AI output reaches a client.
• Keep it one page — longer policies don't get read.

Audit the tools you already pay for.

To avoid buying what you already own:

• Your CRM, email, docs, and accounting stack likely ship AI features you haven't switched on.
• Compare built-in capability vs. a new subscription before you buy.
• Create a one-line "what we need from AI" spec to filter demos.

Train your team. Name an internal owner.

To build a culture of AI literacy:

• Run one 2-hour prompting session using your real documents — not toy examples.
• Name one internal owner (not a committee) for roadmap, questions, and momentum.
• Subscribe the owner to one AI newsletter and one industry report per quarter.

Run one small pilot. Measure it. Decide.

To turn readiness into results:

• Pick the highest-ROI workflow from step 02. Ship it in 30 days.
• Compare hard numbers against your baseline (step 03).
• Expand what works; kill what doesn't. Repeat quarterly.