AI & Automation
AI Readiness Assessment
Before you buy anything.
An AI readiness assessment is a structured review of four things, your data, your file permissions, the processes you might automate, and the licences you already own, ending in a written, ranked answer about what is worth doing and what should wait. happier IT runs it for Canadian organizations of roughly 15 to 200 people, and it frequently concludes that the first job is not an AI job.
Who it's for
People arrive here holding a quote, or holding a worry.
The assessment answers both, because they turn out to be the same question: who can see what, and which work is consistent enough to hand over.
You have a licence quote and no way to judge it. Someone demonstrated a tool, the demonstration was genuinely good, and there is no internal person whose job it is to say whether it would work here. That is a reasonable position to be in.
You suspect the data is not ready. Files in three places, an old server that was migrated by copying everything, and nobody quite sure who can open what. That instinct is usually right, and it is exactly what this measures.
A board or an owner has asked for a plan. Not a strategy deck: a short list of what to do, in what order, with numbers against it. That is the deliverable.
Staff are already using AI and you would like to get in front of it. Approving one good tool tends to work better than blocking twenty, and the assessment is where the approved list gets decided. See AI governance and policy.
The one-minute version
happier IT publishes a nine-question self-assessment that takes about a minute and returns a readiness rating with recommendations, followed by a consultation if you want one. It is free and there is no obligation attached to it.
It is a starting point, not the engagement below. It tells you roughly where you stand; the full assessment tells you what to do.
What's included
What we look at, and what you get back.
Most of the effort goes into permissions and process. Very little of it is about choosing a model, which is the part people expect.
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A permissions and oversharing report
Microsoft states that Copilot only surfaces organizational data a user already has at least view permission to. So an AI assistant does not create oversharing, it makes existing oversharing findable. We report on broadly shared sites, "anyone with the link" sharing, and permissions inherited from an old file server.
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A data-quality read on the systems that matter
Duplicate customer records, inconsistent naming, mandatory fields nobody fills in, and documents whose current version is genuinely ambiguous. This is the single most common reason an AI project disappoints, and it is visible before you spend anything.
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A process inventory with volumes against it
What repetitive work happens here, how often, how many people touch it, how consistent it is, and how often the exception path is taken. Frequency and consistency decide what is worth automating. A painful task done twice a month rarely is.
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A licence audit before anyone buys anything
Organizations routinely already own capability they have not switched on. We check what your current Microsoft 365 plans include, whether Copilot Chat is already available to your staff at no additional cost, and what a paid add-on would genuinely add.
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A shadow-AI check
Which AI services staff are already signed in to, on which accounts, and with what data. Not to discipline anyone, to work out what people actually needed, because that is the most honest requirements document you will ever get.
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A written, ranked recommendation
Every candidate scored on value, effort, and risk, in one table, with the ones we recommend against listed too and the reason given. If the answer is "fix the permissions first and revisit in six months", the document says that.
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A costed pilot proposal for the top one or two
Scope, timeline, price, the measure of success agreed in advance, and the date you decide. Written so you could take it to another provider, which is the point.
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A walkthrough with whoever has to decide
An hour, with the document open, answering questions in plain English. A report nobody reads is not an assessment. It is a PDF.
How it works
Two weeks, three conversations, one document.
Deliberately short. An assessment that takes a quarter has become a project of its own.
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Read-only look at the environment
With your permission, a read-only review of your Microsoft 365 tenancy, sharing, site sprawl, licence allocation and identity setup, plus a look at whichever line-of-business systems hold the work. Nothing changes during this.
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Talk to the people doing the work
Short conversations with three or four people who actually run the repetitive processes, not only with management. What takes time is nearly always something different from what the org chart predicts, and this is where the useful candidates come from.
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Rank it, price it, present it
Findings become a ranked list with effort and risk against each item, a costed pilot for the top one or two, and an hour with you to go through it. You own the document and can act on it with anyone.
What it costs
Fixed price, and worth buying on its own.
It is scoped so you can buy it without committing to a build, and so that the output is useful even if you never work with us again.
Two things move it: how many Microsoft 365 sites and how much content arrived from an old file server, and whether you hold regulated information that needs a closer look.
The free IT assessment and the nine-question AI self-assessment cost nothing and answer a smaller question. Use them first if you are not sure this is what you need.
If you go on to a build, the assessment fee is not a deposit and we do not discount it into a project. Keeping it separate is what lets us recommend doing nothing.
What "not ready" actually means
It almost never means your business is behind. It usually means one of three ordinary things: permissions inherited from a file server migration, a process that varies by who runs it, or records that disagree with each other.
All three are fixable with normal IT work, on a normal budget, and none of them require an AI project to fix.
Why us for this
The assessment we would want if we were buying.
The reason this page exists as its own service is that the alternative is a vendor assessment, and a vendor assessment tends to conclude that you should buy the vendor’s product. Ours is priced as its own piece of work so that "wait" is an available answer.
Two things we will look at that a licensing conversation will not. First, whether the knowledge you want searchable is even inside Microsoft 365: often it is in a line-of-business system, and that is an integration question, not a licence question. Second, whether the process is consistent enough to automate at all.
Our Microsoft certifications are listed in full on our awards and certifications page.
Go deeper
- Microsoft 365 Copilot deployment Where a readiness answer usually leads next.
- Business process automation The candidates the process inventory turns up.
- Free IT assessment The wider, no-cost version.
Questions
What people ask before they sign anything.
What is an AI readiness assessment?
It is a structured review of whether your organization can get value from AI tools yet, covering four areas: file permissions, data quality, process consistency, and the licences you already hold. The output is a ranked written list of what to do and what to leave, with costs. It is not a technology selection exercise, choosing a product is the easy part and comes last.
How do we know if we are ready for AI?
Three questions answer most of it. Can you say who has access to each folder of sensitive material, without checking? Is the process you want to automate done the same way by everyone who does it? Do your key systems agree with each other about basic facts like a customer’s name and status? Three yeses means you are ready to pilot something. One no is worth fixing first, and it is ordinary IT work rather than an AI project.
How long does an AI readiness assessment take?
About two weeks for an organization of 15 to 200 people, most of which is scheduling rather than analysis. The environment review is a couple of days, the staff conversations are three or four hours in total, and writing it up takes a few days. If a provider proposes a three-month assessment for a company your size, ask what happens in months two and three.
What does an AI readiness assessment cost?
There is also a free nine-question self-assessment that takes about a minute and returns a rating with recommendations, which is a reasonable place to start if you are not yet sure the paid piece is worth it.
Will you just tell us to buy Copilot?
Sometimes, because for organizations whose work genuinely happens in Microsoft 365 and whose permissions are tidy, it is the shortest route to value and it requires no build. But the assessment regularly concludes something else: that the knowledge people need lives in a line-of-business system Copilot cannot see, that two small automations would save more time than a fleet of licences, or that the permissions need three weeks of attention before anyone should be buying anything.
Do you need access to our systems to do this?
Read-only access to your Microsoft 365 tenancy for the review, granted by you and removed at the end. Nothing is changed during the assessment. For line-of-business systems we usually work from a screen share and a conversation with whoever administers them rather than asking for credentials. If you would rather we saw nothing directly, we can run a reduced version from exports, and the report will say which parts were less certain as a result.
Is this the same as the free assessment on your site?
No. The free version is a nine-question self-assessment taking about a minute, returning a readiness rating and recommendations, with an optional consultation. This is a paid engagement with a read-only review of your actual environment, conversations with your staff, and a ranked, costed written plan. Start with the free one if you want a sense of where you stand.
Related
Where to go next.
What usually comes next
Related services
Worth reading
Want to know what this would look like for you?
A 30-minute call. No slides, no audit fee, no obligation. We ask what is breaking and tell you honestly whether we are the right fit.