Strategy & Advisory · AI Consulting

AI readiness assessment: find out what AI would see in your company

An AI readiness assessment is a look at where your company's data lives, who can open it, and how your team spends its day, so you know where AI tools like Microsoft Copilot and ChatGPT will save time and what to lock down first. It's for small and mid-sized businesses that want to use AI without it showing the wrong people the wrong files.

You get a written roadmap. You can buy it on its own, with no managed IT contract needed.

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Your written roadmap covers

  • Fix first: the gaps to close before more AI
  • Quick wins: where AI can help your team now
  • Which AI tools to keep, approve or drop
  • What isn't worth it yet, and why
  • A clear next step

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What we check

What our AI readiness assessment looks at

AI tools don't need new access to your company. They use the access your people already have. So most of the assessment is about that access.

  • Where your files actually live

    Email, OneDrive, SharePoint, Teams chats, shared drives, and the line-of-business apps your team logs into. AI can only help with information it can reach, and it can only leak information it can reach.

  • Who can open what

    We look for the folders shared with “everyone” years ago, the links that work for anyone who has them, and the accounts of people who left but were never fully shut off. These are the things an AI assistant will happily find for the wrong person.

  • The AI your team already uses

    Free ChatGPT accounts, browser add-ons, meeting note-takers that join calls on their own. Most of this was set up by staff trying to save time, not by IT. We list what's in use and what data is going into it, without making anyone feel caught.

  • The work that repeats

    The weekly report someone rebuilds by hand, the inbox that gets sorted the same way every morning, the meeting notes nobody has time to write. We talk to the people who do the work and note where AI could take some of it off them, and where it shouldn't.

  • The basics underneath

    Multi-factor authentication (a second step when someone logs in), device protection, backups, and what your Microsoft 365 licenses already include. If these aren't solid, they go to the top of the roadmap.

Microsoft 365 Copilot

Copilot readiness: why permissions come first

Microsoft 365 Copilot answers questions by searching everything the person asking is allowed to open. That's what makes it useful. It's also why a messy file share becomes a real problem the day Copilot is switched on.

A Copilot readiness assessment finds that kind of oversharing and fixes it first. Then you can decide who gets Copilot licenses, starting with the people whose work it actually helps.

For example

A quick example of how it goes wrong: a spreadsheet of salaries was shared with the whole company five years ago by mistake. Nobody has opened it since, so nobody noticed. Then someone asks Copilot “what are we paying the marketing team?” and gets an answer.

What you get

A written roadmap you can act on

At the end you get a written roadmap, in plain language, that covers:

  • Fix first: the sharing, access and security gaps to close before anyone turns on more AI.
  • Quick wins: the tasks where AI can help your team now, with the tool that fits each one.
  • Tools to keep, approve or drop: what to do about the AI apps staff are already using.
  • Not yet: the ideas that aren't worth it today, and why.
  • Next step: what we'd do next, and roughly what it involves.

The roadmap is yours. You can work through it with us, with your current IT provider, or on your own.

If you want help with the rollout, see AI consulting for the Copilot setup, AI use policy and staff training.

Signs it's time

When an AI readiness assessment makes sense

Most businesses call us because one of these just happened:

  • Microsoft keeps offering Copilot in your admin portal and you can't tell if it's worth paying for.
  • You found out someone pastes client emails or contracts into a free AI tool.
  • A customer's security questionnaire asked about your AI policy, and you didn't have one. Compliance support
  • Leadership wants an AI plan for next year's budget. IT strategy and vCIO services
  • You've got a task in mind to automate and want to know if it's safe to hand to AI.

If none of these fit yet, that's fine too. The call will tell you whether now is the right time.

Good to know

What an AI readiness assessment isn't

It isn't an audit or a certification. We don't sign off on anything for regulators or customers. If you need a formal audit, that has to come from an independent auditor, and we can help you get ready for one.

It isn't a sales pitch for licenses. Sometimes the right answer is to clean up permissions and wait. We'll say so.

Done by the engineers who manage Microsoft 365 every day

The assessment is done by Generation IX's own engineers and security team, the same people who set up and secure Microsoft 365 for businesses as part of our managed IT services and managed security. They know where permissions usually go wrong because they clean them up for a living.

Getting started

How the assessment works

  1. Schedule a call

    Tell us which AI tools you're looking at and what you'd like them to do. We'll say plainly whether an assessment is the right first step.

  2. We do the assessment

    We review your accounts, sharing and security settings, and talk with the people who do the repetitive work.

  3. You get the roadmap

    We go through it with you and answer questions, then you decide what happens next.

Trusted by businesses since 1996

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  • Shamrock Capital
  • Ehrlich Yanai Rhee Chaney Architects
  • Cronos Group
  • Light Field Lab
  • 3 Arts

Client stories

What our clients say

FAQ

Questions about AI readiness assessments

Don't see your question? Send us a message.

What does an AI readiness assessment cover?

It covers where your company's data is stored, who can open it, which AI tools your staff already use, which repetitive tasks AI could help with, and whether your security basics are in place. You get a written roadmap with what to fix first and where AI can help.

What is oversharing in Microsoft 365?

Oversharing is when files or folders are open to more people than need them, like a folder shared with the whole company or a link anyone can use. It's easy to miss until an AI tool like Copilot starts pulling those files into answers.

Do we need a Copilot readiness assessment if we haven't bought Copilot yet?

That's the best time to do one. You find out whether Copilot is worth it for your team and fix permission problems before anyone has a license, instead of after.

Is an AI readiness assessment the same as an AI audit?

No. An AI readiness assessment is a practical review to help you plan and fix things. It isn't a formal audit or certification. If a customer or regulator needs an independent audit, we can help you prepare for it.

Is an AI readiness checklist enough?

A checklist tells you what questions to ask. An assessment answers them for your own systems, for example which folders are open to everyone and which AI tools your staff are actually using.

What happens after the assessment?

You keep the roadmap and decide. You can carry it out with Generation IX, with your current IT provider, or on your own.

Want to know what Copilot would find in your files?

Schedule a call. Tell us how your team works and which AI tools you're considering, and we'll tell you whether an assessment makes sense now or can wait. No managed IT contract needed.

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