The Copilot Readiness Assessment: 12 Questions to Ask Before You Spend ~$360/User/Year

Helen Jones
February 4, 2026

Stop. Put the credit card down.

Microsoft Copilot is an incredible tool, but buying 50 licenses on a Monday doesn’t mean you’ll have a productive team on Tuesday. Whether you are looking at the $21/user/month (SMB) promo or the standard $30/user/month (Enterprise) add-on, the bill adds up fast.

For many businesses, a hasty rollout just means a $1,500+ monthly bill and a team wondering why "the AI" isn't doing their job for them.

Before you roll out Copilot (or if you already have and it's flopping), take this 5-minute Readiness Assessment.

Part 1: The "Oversharing" Test (Data Readiness)

Copilot respects your existing permissions. That’s the feature—and the danger.

  • The CEO Salary Test: If an intern asked Microsoft Search "What is the CEO's bonus structure?", would they find a document? (If yes, Copilot will serve it up on a silver platter).
    • (Score 1 point for NO)
  • The "Draft" Graveyard: Do you have 15 versions of "Project_X_Proposal_Final_v2_REAL.docx" saved in SharePoint? (Copilot might pull data from the wrong one).
    • (Score 1 point for NO - i.e., you use proper version history)
  • The Transcript Trap: Do your meetings have "Record and Transcribe" enabled with persistent access policies? (If not, you lose the ability to generate post-meeting summaries).
    • (Score 1 point for YES)
  • The Labeling Habit: Does your team use Sensitivity Labels (Public vs. Internal vs. Confidential) consistently?
    • (Score 1 point for YES)

Score (0-4): ______ If you scored <3: You are effectively weaponizing your own messy data. Fix permissions first.

Part 2: The "Blank Page" Test (People Readiness)

The tool is only as good as the operator.

  • The Prompt Cap: Can your average employee write a prompt longer than 6 words? (e.g., "Write a report" vs. "Act as a Project Manager and draft a status report based on these 3 files...")
    • (Score 1 point for YES)
  • The Skepticism Index: Does your team blindly trust computer output? (Copilot will hallucinate. If they don't catch it, you have a liability).
    • (Score 1 point for NO - i.e., they fact-check active)
  • The "Notion" Factor: Is your team used to "working out loud" (writing things down)? (Copilot can't read minds; it needs written context).
    • (Score 1 point for YES)
  • The Time Investment: Is leadership willing to let productivity dip for 2 weeks while people learn? (If you expect instant wins, you will be disappointed).
    • (Score 1 point for YES)

Score (0-4): ______ If you scored <3: Your team isn't ready for a Ferrari; they’re still learning to drive stick. Training isn't optional.

Part 3: The "Business Case" Test (Value Readiness)

What are we actually solving?

  • The Specificity Use Case: Can you name 3 specific, repetitive tasks that should be automated right now? (General answers like "email" don't count).
    • (Score 1 point for YES)
  • The "Math of Inaction": Do you know how much your "busy work" is currently costing you? (You can't calculate ROI if you don't know the Cost of Inaction).
    • (Score 1 point for YES)
  • The Champion: Do you have one person (not IT) who is obsessed with making this work? (You need a "Copilot Captain").
    • (Score 1 point for YES)
  • The Definition of Done: Do you know what "success" looks like in 30 days? (e.g., "Meeting time reduced by 20%").
    • (Score 1 point for YES)

Score (0-4): ______ If you scored <3: You are buying a solution looking for a problem.

The Verdict

Total Score: 0 - 6 (The Danger Zone) Status: NOT READY. If you deploy now, you will likely see data leaks, frustration, and an eventual cancellation of licenses. Save your money. Focus on "Digital Housekeeping" first.

Total Score: 7 - 10 (The Caution Zone) Status: PROCEED WITH GUARDRAILS. You have the basics, but you lack a system. You will likely get "some" value, but standard usage will plateau quickly.

Total Score: 11 - 12 (Ready for Liftoff) Status: GO. Your data is clean, your people are curious, and your goals are clear.

So, how do you fix a low score?

Most companies fail at Part 2 (People) and Part 3 (Business Case). They buy the tech but forget the methodology.

At Collab365, we help and support businesses get the most out of systems that they purchase like Copilot. We offer training courses, advice, and information to ensure you maximize your investment.

If you want to move from "Danger Zone" to "Liftoff," we have two paths:

  1. For Teams: Join the Microsoft 365 Copilot Business Challenge. It’s a hands-on sprint designed to fix the "Blank Page" problem and build real business use cases in real-time. Click here for more information.
  2. For HR Leaders: Check out our Build an HR Copilot Agent course to see how to maintain governance while automating the heavy lifting of HR queries. Click here for more information.

If you are a Collab365 Academy Platinum Member, these courses are available for you at no extra cost. 

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