TL;DR
An AI readiness assessment for a 5 to 50 person company comes down to five questions about how the business runs, with no technology audit involved: can a computer see your customers and jobs, is the work repeatable, will anyone use what gets built, can your tools talk to each other, and who checks what the machine says before a customer reads it. Our free 20-question scorecard scores those five areas out of 100 in your browser. Under 40 means fix the customer list and the phone first; 40 to 69 means one fixed-price build from $1,000 will pay off and a program will not; 70 and up means a 90-day program will stick. The Census Bureau's own survey puts AI use at 17 to 20 percent of US businesses and under 20 percent of firms with four or fewer employees, so a low score is the norm, not a verdict.
Every AI readiness assessment ranking on Google is a consultancy's intake form. You answer thirty questions, a salesperson calls, and the answer is a six-figure roadmap. That is the right product for a hospital system. It is the wrong product for a plumbing company with eleven people, a Jobber account and a group text that runs dispatch. This guide is the assessment we run on the first call with a contractor or a professional firm, with the scoring shown and the prices attached to each result, so you can run it on yourself before anyone calls you.
What readiness means when you have eleven employees
The enterprise version measures model governance, data lakes and a chief AI officer. None of that is on the table under 50 people, and pretending it is produces the two failure modes we see most: the owner who buys an AI phone agent before the leads are logged anywhere, and the owner who hires a consultant to write a strategy for a company whose quoting lives on carbon paper. Readiness at this size is whether the next automation will have anything to automate.
The numbers say most small companies are early. The Census Bureau's Business Trends and Outlook Survey, collected December 14, 2025 to May 3, 2026 and published May 26, 2026, found overall AI use hovering between 17 and 20 percent of US businesses. Thirty-seven percent of firms with 250 or more employees use it. Fewer than 20 percent of firms with four or fewer employees do, and use did not change significantly among firms under 20 employees over the period. The Federal Reserve's April 3, 2026 note on the same survey puts the year-end 2025 figure at about 18 percent, with professional services near 33 percent and accommodation and food service near 8 percent. One caveat the Census publishes with the data: the question changed in November 2025 from "producing goods or services" to "any business function," so the jump from earlier years is partly the wording. Two things follow from those figures. Most of your competitors are not using AI either, so there is no urgency premium. And what separates a four-person shop from a 250-person company is that the bigger one already has its data in one place.
The five areas, and why each one is a gate
1. Data: can a computer see your business?
Four questions. Where a new lead's name ends up. Where quotes, jobs and invoices live. How long it takes to pull last month's leads, booked jobs and revenue. Whether inbound calls are logged anywhere. A company that scores under 8 here cannot automate follow-up, because there is nothing to follow up from, and cannot build a dashboard, because there is nothing to display. The fix is cheap and boring: one CRM every lead source feeds, a tracking number on the website and the Google listing, and the job software connected to QuickBooks. Our guides to CRM for contractors and which CRMs sync two ways with QuickBooks cover the choice. None of it is AI, and all of it is what the AI will read.
2. Workflows: is the work repeatable?
Whether the path from lead to booked job is written down. What happens when a quote goes quiet. How a job gets from the office to the crew. Whether you can name one task three or more people do the same way every time. Software can only repeat something that already repeats. If the quote follow-up depends on who remembers, an automated sequence will fire into a process nobody owns, and the first time it texts a customer who already paid, it gets switched off. The lead follow-up system is the written version of the first workflow most contractors need, and eight tasks you can automate today is the list to pick from once one path is written down.
3. People: will anyone use it?
Who owns the software. Whether anyone has used ChatGPT, Claude or Gemini for work this month. How long a new office hire takes to learn the systems. What happened the last time you changed a tool. This area kills more projects than the other four combined, and it is the one no vendor assesses, because the honest answer costs them the sale. A company where the owner is the only person who can change a setting is a company where every automation becomes the owner's problem at 9 pm. If the score here is low, the right first purchase is four sessions with the people who will run it, before any software, which is what the AI and Automation Coaching Sprint is for at $1,000, and the one shared AI platform decision comes before any build.
4. Tools: can your software talk to anything?
Whether the CRM has an API or at least a Zapier or Make connection. Whether the phone system logs calls and can text. Whether accounting and the job software sync. How many logins the office uses before lunch. This is the area owners expect an assessment to be about, and it is the fourth gate, not the first. A CRM with an API is worth nothing if the data in it is incomplete. The common pattern at a 60-point company is a good tool set wired to nothing: Jobber, QuickBooks, a VoIP line and a website that each hold a piece of the customer and never compare notes. The build that fixes that is usually the cheapest one on our list.
5. Risk: who checks what the machine says?
Whether you have a written AI use policy. Who sees an automated message before a customer does. Where customer data lives and who can reach it. How you would find out a tool broke at 2 am. Small companies skip this area because it sounds like compliance. It is operations. We have watched a missed-call text back fire on 200 callers who had just spoken to the owner because one callback URL was wrong, and nobody knew for 17 days because nothing was watching. A policy at this size is one page: what the team may paste into an AI tool, what must never leave the CRM, and who approves anything a customer reads that a person did not write. That page is the AI policy template, a free Word download.
Score it: the 20 questions
Each question scores 0, 2, 3 or 4, and 5 for the best answer. The scorecard tool does the arithmetic live and shows the two weakest areas with the first fix in each. The table is the same twenty questions with the 0-point and 5-point answers, so you can score it on paper in a truck.
| Area | Question | 0 points | 5 points |
|---|---|---|---|
| Data | Where does a new lead's name and number end up? | Someone's head or a text thread | A CRM, every lead, every source |
| Data | Quotes, jobs and invoices live in | Paper or a phone's photo roll | One system, synced to accounting |
| Data | Time to pull last month's leads, jobs and revenue | Days, and someone has to build it | Ten minutes, one screen |
| Data | Inbound calls are | Not logged anywhere | Logged, recorded, tied to the customer |
| Workflows | Is lead to booked job written down? | No, it depends who picks up | Written and followed |
| Workflows | A quote goes quiet. What happens? | Nothing, unless they call back | An automatic sequence with a human at the end |
| Workflows | How does a job reach the crew? | A group text or a call | Dispatch software, no side channel |
| Workflows | One task three people do the same way | Cannot think of one | Most of the office runs that way |
| People | Who owns the software? | Nobody | A named person with time for it |
| People | Anyone used ChatGPT, Claude or Gemini for work this month? | No | Most of the office, shared account |
| People | A new office hire learns the systems in | Months, by shadowing | Days, from written steps |
| People | Last time you changed a tool, the team | Kept the old way | Asked for it |
| Tools | Your CRM or field service software | Does not exist | Has an API you already use |
| Tools | Your phone system | Is a cell phone | Logs, records, texts, talks to the CRM |
| Tools | Accounting and job software | Re-keyed by hand | Sync both ways |
| Tools | Logins before lunch | Eight or more, some shared | One or two, single sign-on |
| Risk | Written AI use policy? | No | Written, signed, reviewed this year |
| Risk | Who sees an automated message before a customer? | Nobody, it just sends | A person approves anything not a template |
| Risk | Customer data lives | In texts, photos, personal email | In the CRM, with roles |
| Risk | A tool breaks at 2 am. You find out | When a customer complains | That night, from an alert |
| Total | Under 40: fix data and the phone. 40 to 69: one build. 70 and up: a 90-day program. | ||
Score yourself in four minutes
The scorecard runs in your browser, no email needed. Leave one if you want Alex to read your answers and reply with what to buy first, or that you need nothing yet.
What each score should buy
This is the part the consultancy assessments leave out, because their answer is always the same. Ours changes with the number, and every price below is on our pricing page.
Under 40: not ready, and that is fine
Automating a process that lives in a group text automates the mess. The first month is a $100 Jobber or Housecall Pro seat if you have neither, a tracking number with missed call text back, and one CRM every lead goes into. That is a month of office work, not a project, and most companies can do it without us. If the phone side is the blocker, Essentials at $350 a month includes call tracking, the text back and the review funnel on a site we build. Do not buy an AI phone agent, a dashboard or a consultant at this score. There is nothing for them to read.
40 to 69: ready for one build
Enough is in place to automate one thing well, and not enough for three. Pick the leak that costs the most. For most trades it is quotes that go quiet, which is a follow-up sequence; for an office that re-keys invoices, it is the QuickBooks sync; for a company missing calls, it is the AI phone agent. One fixed-price build from $1,000, scoped in writing, done in two to four weeks, and you see it on screen before it is built. A company at 55 that buys a 90-day program spends the first month doing the data work it could have done itself.
70 and up: ready for a program
The data is in one place, the work repeats, someone owns the software and the tools already connect. This is the company the Systems Sprint was built for: a custom CRM in month one, a proposal system in month two, an owner dashboard in month three, $2,500 a month for three months or $6,750 up front, and you own all of it. After that, $500 a month keeps it running and builds the next thing, or you run it yourself with the documentation. At this score the risk is scope rather than the build, which is why each month ships before the next one is paid for.
Three things that fake readiness
A ChatGPT subscription. The owner uses it daily, so the company "uses AI." The Census question is about business functions, and a chat window on one laptop does not qualify. Count it as a good sign for the People area and nothing more.
An expensive CRM nobody fills in. ServiceTitan at $400 a month with half the leads in it scores lower on Data than a $29 Jobber seat with all of them. Every assessment that asks "which software do you use" instead of "where does a lead end up" gets this backwards.
A consultant's roadmap. A 40-page document with phases and a maturity model, for a company that cannot pull last month's revenue in under a day. Strategy at this size is the order of operations above. If a proposal does not start with the customer list and the phone, it was written for a different company.
What a 90-day plan looks like at each score
The question we hear after the score is "then what, in order." Three plans, one per band, each a month per line.
| Band | Month 1 | Month 2 | Month 3 |
|---|---|---|---|
| Under 40 | Pick the CRM, move every lead source into it, put a tracking number on the site and the listing | Turn on missed call text back and the review request; write down lead to booked | Connect accounting; re-score. Most companies land in the 50s. |
| 40 to 69 | Scope one build in writing, see it on screen | Ship it, train the two people who touch it | Thirty days of fixes; measure the leak it was meant to close |
| 70 and up | Systems map in week one, then the CRM build | Proposal system, chased until paid | Owner dashboard, training, documentation, hand over the keys |
Want the score read by a person?
Thirty minutes. We tell you whether you need a build, a program, or a software seat you can buy yourself this afternoon. If it is the seat, we say so.
Frequently asked questions
What is an AI readiness assessment?
A structured check of whether a business can get value from automation or AI before it spends on either. For a company under 50 people the useful version measures five things: whether the customer and job data is in one system, whether the work is repeatable, whether anyone will own the result, whether the tools can connect, and whether someone checks what automated systems send to customers.
What is a good AI readiness score for a small business?
Seventy or above out of 100 on our scorecard means a 90-day program will stick. Forty to 69 means one well-chosen build will pay off. Under 40 means the customer list and the phone come first. Given that fewer than 20 percent of firms with four or fewer employees use AI at all, by the Census Bureau's count, most honest scores land under 60.
How is this different from an AI audit?
An AI audit reviews systems you already run: what the tools do, what they cost, where they fail. A readiness assessment runs before anything is bought. If you already have automations in place and want them checked, that is a different call, and the scorecard's Risk area is the place it overlaps.
Do I need an AI strategy before I automate anything?
Not a document. For a company this size the strategy is the order of operations: data in one place, then the phone, then one build, then a program. The score tells you which step you are on, and the plan table above is the whole roadmap.
How much does AI readiness consulting cost?
Enterprise firms charge $10,000 and up for an assessment and roadmap. Ours is free in the scorecard and 30 minutes on a call. The paid options after it are a $1,000 Coaching Sprint of four live sessions, one build from $1,000, or the Systems Sprint at $2,500 a month for three months.
Does the scorecard send my answers anywhere?
No. The score is computed in your browser. If you leave an email, your twenty answers go to Alex and you get one reply, not a sequence.