October 8, 2026
Questions an AI consultant should ask you
The questions a competent AI consultant asks before quoting: the work, the systems, your Ontario headcount, personal information, and when to stop.
Sheet 41 A/9 · Southern Georgian Bay Ed. 2026
Ontario · Assessment $999
Statistics Canada asked businesses that skipped AI why. Cost came fourth, at 10.6%. Security came third, at 13.4%. First, at 40.0%: AI is not relevant to what they do. That is almost never true. It is what not knowing where to start sounds like on a survey.
$999 Once. In 10 business days you know the three jobs to automate, and what each one is costing you now.
Credited in full against any automation project you go ahead with.
Survey of the territory
19.2%
of Canadian businesses used AI in Q2 2026
Up from 6.1% two years earlier. Statistics Canada.
Source: www150.statcan.gc.ca40.0%
of non-adopters said AI is "not relevant" to them
The top reason given, ahead of security at 13.4% and cost at 10.6%.
Source: www150.statcan.gc.ca9.9%
adoption among rural businesses, against 21.0% urban
An eleven point gap inside the same economy.
Source: www150.statcan.gc.ca$15,000
available to Ontario SMEs for a digital adoption plan
Ontario Centre of Innovation, DMAP, first come first served.
Source: oc-innovation.caSurveyed by www150.statcan.gc.ca, oc-innovation.ca. Every figure on this sheet links to the release it came from.
What I do
The assessment comes first, always. It is the only one of these I will sell to somebody who has not already decided what they want, because the other three are builds and a build aimed at the wrong job is the most expensive thing on this page.
The one product
Every service above is an engagement: scoped, quoted, delivered, finished. Windfall is the exception and it is sold by the month, because the work it does is the work that repeats. It is listed separately rather than as a fifth card, because a subscription and a project are different commitments and putting them in one grid hides that.
Marketing Automation for Small Business
The posting, the email, the follow-up on an enquiry that went quiet, and the monthly report. Running on a schedule, with your approval before anything goes out.
$3,500 then $600 to $1,500
Setup once, then monthly. Channels and volume drive it
How Windfall worksFind your job
The starting point decides the engagement, and the wrong starting point is expensive. Find the one that sounds like your week. It maps to what is causing it and to the work that actually addresses it.
None of these quite right? Book the 15 minute call and describe the week instead. The pattern is usually obvious to somebody who has seen it before and invisible from inside it.
Where I work
A Brampton logistics firm, a Waterloo software company and a Sault Ste. Marie contractor are not running the same business, and the automation that pays in one is dead weight in another. Each city page below says what the local economy actually runs on and which of the four services fits it.
Latest notes
October 8, 2026
The questions a competent AI consultant asks before quoting: the work, the systems, your Ontario headcount, personal information, and when to stop.
October 4, 2026
What to write down before you meet an AI consultant: who decides, every system you pay for, your worst hour, three counted jobs, and where personal data sits.
October 3, 2026
A savings figure before anyone has watched the work, a product before a problem, nothing marked skip. The signs of an oversold AI pitch, and how to test one.
Ten business days of work ending in a written document and a 60 minute walkthrough. Inside it: an inventory of every repeated task in your business that a machine could do, the three worth doing first, an hours-per-week and dollars-per-year figure against each, the specific tools each one needs with their real subscription costs, a build estimate for each, and the ones I recommend you do not do. It is written to be handed to another supplier. If you take it elsewhere and get the work done cheaper, the document did its job.
If you go ahead with any automation project with me after the assessment, the full $999 comes off that project. Not a discount code and not a percentage. The whole fee. So the real choice is $999 for the diagnosis alone, or nothing extra if you also want the work done.
Canadian consultancies that publish rate cards put a readiness assessment at $1,500 to $5,000, and several open at $2,000 or $3,500. Two things make $999 work. The scope is fixed rather than open, so there is no discovery phase billed by the hour. And the assessment is how I find build work, which means it does not have to carry a consulting margin on its own.
Both, and the report is written so you can take it to somebody else. Most builds land between $2,500 and $12,000 depending on how many systems have to talk to each other. The Canadian agencies publishing numbers quote $2,000 to $8,000 for a single workflow and $2,500 to $25,000 for a project, so this is the same market rate, quoted before you have paid me anything.
Statistics Canada measured 19.9% adoption among businesses with one to four employees against 27.8% among businesses with 100 or more. The gap between the smallest firms and the largest is under eight points, which is a much smaller gap than most owners assume. Small businesses adopt at close to enterprise rates because one person wearing four hats has more repeated work per head, not less.
It depends entirely on which tools, and this is a real question rather than a formality. In May 2026 the Privacy Commissioner of Canada found that OpenAI's initial training of ChatGPT did not comply with Canadian privacy law. PIPEDA applies to personal information in prompts, in retrieval corpora and in model outputs exactly as it applies to a database. Part of the assessment is saying which of your processes can use a consumer chatbot and which need something that keeps the data inside your own systems.
Possibly, and it is worth checking before you pay me. The Ontario Centre of Innovation runs a Digital Modernization and Adoption Plan worth up to $15,000 toward exactly this kind of planning work, for Ontario for-profit SMEs with one to 499 employees, on a first come first served basis while funds last. Eligibility, timing and the application are yours to run, not mine, and I will not claim an approval I cannot control. Tell me on the call if you are applying and I will write the assessment so it lines up with what that application asks for.
Then it says that, and you have saved a five figure build. It happens most often with businesses under about five people, where the repeated work is real but does not yet add up to enough hours to pay back a build, and with businesses whose actual problem is that nobody has written down how the work is done. You cannot automate a process that only exists in one person's head.
You are here
Tell me how many people work there, what the busiest hour of the week looks like, and which task everybody complains about. That is usually enough to say on a first call whether an assessment is worth your $999 or whether you have one obvious problem that needs one obvious fix.
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