AI readiness checklist for service businesses
Thirty questions in five groups: phones, intake, systems, people, money. Answer them in a room with the people who do the work. The gaps are the first project.
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Who it is for
Owners and office managers deciding whether the business is ready for an AI project, and which one to do first.
Readiness is thirty questions in five groups: phones, intake, systems, people, money. Answer them in a room with the people who do the work, from records where they exist, and write down every question nobody can answer. The gaps are the first project. Nobody needs a good score to start, only to know which group the project depends on.
What does readiness mean for a service business?
Not whether you are technical. Not whether you have a data team. Readiness for a service business is whether the thing the AI would do is measurable, whether the systems it would touch can be trusted, and whether one person inside the business will own it. Those three are what a failed project is usually missing, and none of them costs money to fix.
The thirty questions below sort into five groups of six. Each question has the answer a ready business gives. Score each group by counting the clear yes answers, and read the scores as a map, not a grade. The group that scores lowest is not a reason to do nothing; it is the list of what to fix before you start, and the fix is usually a tally sheet, a field, or a decision.
What should I ask about the phones?
Question 1. Do we know how many calls we miss in a month? The ready answer is a number from the phone system's log, after-hours calls included, and the date it was pulled. If the answer is a guess, the fix is a call log or a one-week tally sheet, and it is the first thing to do. Where we have a measured deployment that started with the call log, its number reads Timeline set in the working session.
Question 2. Do we know what callers want? The ready answer is a short list, in the callers' own words, from a week of listening: book, quote, where is the tech, emergency, billing. If nobody has written it down, spend a week writing it down; every agent you might ever build starts from that list.
Question 3. What happens to a call after hours today? The ready answer names the voicemail, the answering service, or the owner's cell, and says what happens to the message on Monday. If the honest answer is "nothing until Monday," the money group will tell you what that costs.
Question 4. Can the phone system send a call somewhere else? The ready answer is yes, with the name of the phone provider and whether it can forward, ring a group, or hand a call to a webhook. A phone system that cannot forward is a phone system to replace before an agent is built, not after.
Question 5. Is there a recording or a transcript of any real call? The ready answer is yes and here is where they are kept. Real calls are how an agent is tested before it talks to a customer; a business with no recordings tests on imagination.
Question 6. Who answers the phone, and what do they do when it rings while they are on another call? The ready answer names the person and describes the overflow. If the overflow is "it rings out," that is the missed-call count on question 1, seen from the other side.
What should I ask about intake?
Question 7. Where do requests arrive? The ready answer is a list: phone, web form, text, email, a marketplace, a referral partner. Every door counts. A door nobody watches is a leak.
Question 8. Does every door land in one place? The ready answer is yes, one queue, one system, with a timestamp on arrival. If requests live in three inboxes and a notepad, the first project is one queue, and it is not an AI project.
Question 9. How long from request to first reply? The ready answer is a measured number, by door, from the timestamps in question 8. If it cannot be measured, it cannot be improved and it cannot be committed to.
Question 10. How long from request to quote? The ready answer is measured the same way, from the request timestamp to the sent-quote timestamp. Expect this number to be larger than anyone in the room believes.
Question 11. Is there a written list of what a quote needs before it can be priced? The ready answer is a checklist: the measurements, the photos, the access notes, the material choices. If the list lives in the estimator's head, the estimator is the bottleneck by definition.
Question 12. What happens to a quote that is not answered? The ready answer is a follow-up rule: who, when, how many times, through which channel. If the answer is "we wait," the quote-turnaround playbook is the next thing to read.
What should I ask about systems and data?
Question 13. What is the system of record for customers, for jobs, and for money? The ready answer names one system for each, ServiceTitan or Jobber or Housecall Pro for jobs, QuickBooks or its equal for money, and says which one wins when two disagree. Three answers that are all "the spreadsheet" are a fine answer; three answers that are "it depends" are not.
Question 14. Does the system of record have an API, and does someone here have admin rights to it? The ready answer is yes to both, with the person named. An AI tool connects to a system through its API on a credential an admin issues; without both, nothing connects.
Question 15. Are the customer records trustworthy? The ready answer is that a phone number finds one customer, not two, and an address is in the address field, not the notes. Open the system and look up ten customers by phone while you answer. Duplicates are how an agent books the wrong person.
Question 16. Where does something get re-typed from one system into another? The ready answer is a list of every place a person copies a value by hand. Each one is a place a tool could read or write instead, and each one is a place where the two systems already disagree.
Question 17. Is the pricing written down anywhere a machine could read? The ready answer is a price book in the system, a rate card, or a spreadsheet with rules, not a person. If the pricing lives in one estimator's head, no quote tool can be built until it is written down, and writing it down is worth doing whether or not a tool follows.
Question 18. Is there history? The ready answer is a year or more of jobs, quotes and calls in the system of record, with dates. History is what a tool is tested against and what a baseline is taken from. A business that switched systems last month has a systems score, not a data score, and should say so.
What should I ask about people?
Question 19. Who owns this inside the business? The ready answer is one name, with the hours per week that person can give it, written on line 5 of the worksheet. A project with no owner inside the business is a vendor's project, and it ends when the vendor's attention does.
Question 20. Who will be in the room every week? The ready answer is the owner from question 19 plus the person whose work changes, the dispatcher for a dispatch tool, the estimator for a quote tool. If the person whose work changes is not in the room, the tool will be built to how the owner thinks the work is done.
Question 21. Has the team been told, and what were they told? The ready answer is that the people whose work changes have heard, from the owner, what the tool will do and what it will not, and that their jobs are the exceptions the tool cannot handle. A team that hears about the tool from the vendor assumes the worst.
Question 22. Who handles the exception? The ready answer names the person a tool hands off to when it is unsure, and says how they are reached at night. Every tool worth building hands off; a tool with nobody to hand off to has to be right every time, and nothing is.
Question 23. Has anyone here run a change before? The ready answer is a story: the last time the business changed a system or a process, what went wrong, and what they would do differently. A business that has never changed a system is not unready, but it should plan for the change to take longer than the build.
Question 24. What will you stop doing? The ready answer names the manual step that goes away and who agrees it goes away. A tool added on top of a process nobody stops is more work, not less, and the office will quietly go back to the old way.
What should I ask about money?
Question 25. What is the loudest problem worth, in dollars a month? The ready answer is a number with a method: missed calls times average ticket times close rate, or quotes lost to slow turnaround times the average quote. Use the missed-call worksheet on this site. A problem with no number attached is a feeling, and feelings do not survive an invoice.
Question 26. Is there a baseline, with dates? The ready answer is the number from question 25 counted over a stated period, written down before anything is built. A baseline taken after go-live is not a baseline.
Question 27. What is the budget, and is it fixed or hourly? The ready answer is a fixed figure the owner will spend on a defined scope, and a monthly figure for running it. An hourly budget on a project with unknowns puts the unknowns on you.
Question 28. Who pays for the phone, message and model usage each month? The ready answer names the lines: telephony, messaging, model usage, hosting, and who holds each account. Usage bills that arrive on the vendor's card are a surprise later; usage bills on your card are a line item now.
Question 29. What happens if it does not work? The ready answer is written: the metric, the review date, and what the vendor does if the number misses. The written ROI commitment guide on this site is the template. A project with no answer to this question has no way to end well or badly; it just fades.
Question 30. What is the next project after this one? The ready answer is one sentence. A business that can name the second project is doing this for the business; one that cannot is doing it for the first project, which is fine, as long as everyone knows.
How do I score it and pick the first project?
Count the clear yes answers in each group and write the five counts on line 1. Then look for the group that scores lowest, and list the fixes on line 2: the call log, the single queue, the price book written down, the owner named. Those fixes are small, they cost time rather than money, and they make every later project possible. Do them first.
The first project is chosen by two things: the problem with the biggest number on question 25, and the groups that problem depends on. A voice agent depends on the phones and systems groups; a quote tool depends on intake and systems; a dispatch tool depends on systems and people. If the biggest number sits on a problem whose groups scored low, the first project is the fix list, and the AI project is the second. Write the project on line 3 and the baseline on line 4.
Where does this go wrong?
The owner answers every question alone, and every answer is a yes. The office answers alone, and every answer is a complaint. The systems questions are answered from memory with the system closed. The money question gets a number with no method, and the number is the one the owner wants. The checklist is run once, after the vendor is chosen, to confirm a decision already made.
The fix for all of those is the same: the right people, one hour, phones off, the system open, and the sheet filled in before any vendor is in the room. Bring the sheet to a working session and we will tell you which line the project you have in mind depends on, and whether it is the right first project.
Step by step
- 1
Get the right people in the room
The owner, whoever answers the phone, whoever builds quotes, whoever runs the schedule, and whoever does the books. One hour, phones off. The person who does the work answers the question about the work; the owner listens. Most of what an AI project needs to know lives in those people's heads, not in a system.
- 2
Answer the phone and intake questions
The first two groups are about what comes in and what happens to it. Answer from records where records exist, the call log and the form inbox, and from a tally sheet for a week where they do not. Write the answer, not the feeling. Where nobody knows, write that down; it is the most useful answer on the sheet.
- 3
Answer the systems and data questions
The third group asks what software the business actually runs on and whether the data in it can be trusted. Open the system while you answer. A field that exists but nobody fills is a field that does not exist. Name the system of record for customers, jobs and money, and note every place a person re-types something from one system into another.
- 4
Answer the people and money questions
The last two groups ask who will own the project inside the business and what a result is worth. Name one person, not a committee. Put a rough dollar figure on the loudest problem, using the missed-call worksheet or the quote-turnaround playbook, and be honest about how much of the owner's time the project can have.
- 5
Score it and pick the first project
Count the answers per group that are a clear yes. A group with the fewest is not where you start; it is what you fix before you start. The first project is the one whose group scores well on the questions it needs and whose problem carries the biggest number from the money group. Write the baseline for that number, with the date, before anyone builds.
Worksheet
- Line 1. The five group scores, each the count of clear yes answers out of six.
- Line 2. The three gaps you found that have to be fixed before any project starts, each with a name and a date.
- Line 3. The first project, in one sentence, and the group score it depends on.
- Line 4. The metric the first project is measured on, and the baseline for it with the dates it was counted over.
- Line 5. The person inside the business who owns the project, and the hours per week they can give it.
- Line 6. The date you will run the checklist again.
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Common questions
Do I have to answer all thirty questions?
Answer all of them once. The point is not the score, it is the conversation in the room when someone says they do not know. A question you skip is usually the one that would have stopped the project in month two. After the first time, re-run only the group your next project depends on.
What is a passing score?
There is no pass. A group where most answers are a clear yes is ready to carry a project; a group where most are no is a list of things to fix first. A business can score badly everywhere except the one group the project needs and still be the right business for that project.
Does a bad score mean we should not do anything with AI?
It means the first project is smaller than you thought. A business with no call log cannot measure a voice agent, so the first project is the call log. That is not a failure; it is the cheapest useful thing you can do this month, and it makes the next project measurable.
Who should fill this in, the owner or the office?
Both, in the same room. The owner knows what the business is trying to become; the office knows how the work is actually done, and the two are never the same picture. An answer the owner gives alone is a plan; an answer the office gives alone is a complaint. You want the overlap.
Can I use this to evaluate a vendor's proposal?
Yes. A proposal that does not ask for your answers to the money group and the systems group is a proposal written before anyone looked at your business. Hand the vendor your sheet and ask which lines their project depends on. A good vendor will name them.