The Copilot Shift — Episode 4

Preparing Your Business for Copilot: Data, Security, and Culture

Before we all jump into the weekend here’s episode 4 and today, I’ll cover 3 critical preparation steps you won’t want to miss.

Clearly Copilot adoption doesn’t start with buying licenses. It starts with the preparation – the behind the scenes work that determines whether Copilot becomes a tool to help you make those transformations or simply an expensive disappointment. These are simple steps you can follow as a methodology for adoption.

Theres no shortage of information and guidance out there on this but in this episode I want to focus on the three pillars that I would say matter most, and put simply without all the jargon:

  • Your data – where are you maintaining it, are you maintaining it correctly, how is it’s structured, and who can access it
  • Your security – or as the industry now terms as guardrails that keep information safe
  • Your culture – What AI visibility do your employees already have within the business and what do they think about the use AI

When all three of are aligned, Copilot becomes a strategic advantage and will save you considerable time further down the line. But if they’re not, Copilot becomes confused, inconsistent, or even risky, giving inaccurate results and sometimes in the wrong hands.

Let’s look at these three in more detail.


1️⃣ Data Readiness – Regarded as the Heart of Copilot’s Intelligence

It’s all about the business data for AI and this is Copilot’s power. If your data is messy, scattered, or inaccessible, Copilot will struggle to help you effectively. Recommended approaches are:  

✔ Move your files into OneDrive and SharePoint

Copilot can only use what it can see, and it only sees data stored in Microsoft 365.

If your files are still on:

  • Local servers
  • Desktop folders
  • Dropbox
  • Google Drive
  • USB drives

…Copilot won’t be able to use them.

✔ Look to organise your files into logical structures

Copilot thrives on the clarity you create.

We all know file storage is an organic thing and it just spreads so now would be a great time to review this. If possible a simple structure works best:

  • Company-wide documents → SharePoint
  • Team documents → Team sites
  • Personal work files → OneDrive

Its not just Copilot that benefits form this too, maybe your migrating device management to the cloud and Intune. This will massively help the company in that journey too.

✔ It’s now time to lean up old or duplicate content

Copilot doesn’t know which version is “the right one.” If you have:

  • “Final_v3”
  • “Final_v3_REAL”
  • “Final_v3_UPDATED”

…Copilot will treat them all equally.

✔ Fix broken, overly broad or even unnecessary permissions

If “Everyone” has access to everything, Copilot will reflect that.

This is the #1 risk SMBs overlook.


2️⃣ Security Readiness – Implement those guardrails to Protect Your Business

Generally speaking, Copilot isn’t there to review or recommend security improvements. It will respect your existing security model, however that does mean your security must be solid before rollout.

✔ Review access permissions

Ask yourself or security managers:

  • Who should have access to what?
  • Who currently has access to everything?
  • Are there old groups or accounts still active?
  • Setup temporary access to data to limit visibility

It’s important to know that Copilot won’t leak your data, but it will surface data to users who already have access.

✔ PLEASE PLEASE Implement sensitivity labels (recommended)

Labels help Copilot understand:

  • What’s confidential
  • What’s internal
  • What’s public
  • What should never be shared

Even a simple label set makes a big difference.

Bottom Line for SMEs

For 80% of SMEs: Microsoft 365 Business Premium license gives you everything you need for sensitivity labels (using Microsoft Purview). Users can manually classify documents, and you get encryption and visual markers.

You only need E5 if: You need AI to automatically classify documents based on content, or you have regulatory requirements for automated DLP.

Start simple: I recommend deploying manual labels first. If you later discover you need automation, then upgrade specific users to M365 E5 Compliance add-ons.

✔ Enable MFA and Conditional Access

This will protect your environment from unauthorised access – which is especially important when AI tools are involved.

✔ Review your Teams and SharePoint governance if used

If your Teams environment is chaotic, Copilot will unfortunately inherit that chaos.


3️⃣ Cultural Readiness — Preparing Employees for the Shift

Theres a whole industry built around AI adoption. Let’s be clear though, this isn’t just technical. It’s behavioural.

Employees will need to understand:

  • What Copilot is
  • What it’s good at, its strengths
  • What it’s not good at and to avoid
  • How to use it responsibly, always
  • And Importantly – How to write effective prompts (Follow the series for more on this)

✔ Start with a pilot group – Typically 3–5 people in an SME who:

  • Are curious
  • Are open to change
  • Represent different roles
  • Communicate well

You want these people to become your internal champions.

✔ Set expectations early

Copilot is:

  • A productivity tool
  • A creative partner
  • A time‑saver
  • A draft generator

Copilot is definitely not:

  • A replacement for expertise
  • A source of absolute truth
  • Or your decision‑maker

✔ Provide simple prompt templates

Learning how to talk to AI is an art that you learn, so providing guidance early on will be well received. Provide simple examples to start with like:

  • “Draft an email based on this document…”
  • “Summarise this meeting and highlight actions…”
  • “Create a proposal using the attached files…”
  • “Analyse this spreadsheet and identify trends…”

✔ Encourage experimentation

It’s very much like many things in life, the more people use Copilot, the more value they unlock and benefits you see as a company.


4️⃣ The Copilot Readiness Score (Quick Self‑Assessment)

Here’s a quick readiness assessment. Like the other surveys, answer them honestly and keep a note of these for later reference. Rate each area from 1–5:

AreaScore 1–5Notes
Data is stored in OneDrive/SharePoint
File structure is clean and logical
Permissions are accurate and up to date
Sensitivity labels are in place
Teams/SharePoint governance is healthy
Staff understand what Copilot is
Staff know how to prompt
Pilot group identified

If your total score is 28 or higher: You’re ready for rollout.

If your score is 20–27: You’re fairly close so concentrate on fixing the gaps first.

If your score is below 20: Clearly more preparation is your priority before licensing.


🧭 Episode 4 Summary

Thanks for reading. In my experience I would have to say that implementing these changes to prepare your business for Copilot is the most important step in the entire journey. The stricter you can be with these, the better the results.

  • Clean, accessible data
  • Strong, sensible security
  • A culture that embraces AI

Get these right, and Copilot becomes a strategic advantage. Skip them, and Copilot becomes frustrating or ineffective.


📘 Coming Next Week: Episode 5

The Copilot Adoption Stages — A Clear Roadmap for SMBs

This is where I’ll map out the full journey from awareness to optimisation.

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