Common warning signs
What You Will Get
This free checklist walks you through 15 questions that separate a proper managed service from reactive break-fix support — in plain English. Every question includes what to ask, what a good answer sounds like, and red flags to watch for.
This checklist gives you a structured way to separate the premium managed service from the break-fix provider in a tie-dye t-shirt.
Why focusing on price alone is the wrong MSP selection strategy.
15 questions across 4 categories — each with "what to ask", "good answer", and red flags.
Coverage & Scope: what is included in the fixed monthly fee, platform coverage, response times.
Proactive vs Reactive: monitoring, reviews, patching cadence.
Security & Compliance: base security vs premium add-ons, Cyber Essentials support, incident response.
Continuity & Commercial Fit: backups, restore process, contract terms, references, realistic expectations.
75-point comparison scorecard with interpretation bands (60+ strong, 40-59 worth deeper conversation, below 40 red flag).
Provider comparison table (3-column layout for scoring multiple suppliers).
Notes and follow-ups table.
Final decision summary with CTA to book a free Security Triage Call.
Download Your Free MSP Comparison Checklist
The checklist is a printable, fillable PDF that you can work through at your own pace. It takes about 20 minutes and gives you a document you can take to any provider — or use to pressure-test the one you already have.
Do I need technical knowledge to use this checklist?
No. The checklist is written for owner-managed SMEs who are not IT-literate. Every technical term is explained in plain English, and each question includes what a good answer sounds like so you know what to look for.
Is this checklist specific to Microsoft 365?
The checklist covers IT support providers broadly, but uses Microsoft 365 as its primary example since most of our readers use it. The principles apply to any technology stack.
Does completing this checklist commit me to anything?
No. The checklist is a free resource you can use however you like — to evaluate your current provider, compare potential suppliers, or simply understand what a proper managed service looks like. There is no obligation.
What happens after I download the checklist?
You get the PDF instantly. If working through it reveals gaps you are not sure how to close, you can book a free Security Triage Call to discuss your findings with Infinite Cloud IT. There is no obligation.
I am in Kent or Sussex. Can you help with our specific setup?
Absolutely. The checklist is designed to be useful wherever you are, and we regularly work with SMEs across Kent, Sussex and the South East. Book a free Security Triage Call to discuss your situation specifically.
