Free Guide · 2026 Edition
21 Questions to Ask Before You Trust Anyone With Your IT
Every IT company promises to be proactive, responsive and secure. This free guide gives you the 21 questions that reveal which ones actually are, what a good answer sounds like, and the red flags that should make you walk away, before you hand anyone the keys to your systems.
16-page PDF · Instant download · Free
In this guide, you'll learn:
- The 21 questions that separate a dependable IT partner from one that will cost you time, money and sleep.
- What a good answer sounds like for each question, and the red flags that should make you walk away.
- The "not included" trap: how to find out what will trigger an extra invoice before you sign.
- Six costly misconceptions about cybersecurity, backups, Microsoft 365 and cyber insurance.
- A printable scorecard to compare up to three IT providers side by side.
The 21 Questions
Part 1 · Questions 1–5
Support & Responsiveness
Part 2 · Questions 6–11
Proactive Management & Accountability
Part 3 · Questions 12–13
Contracts, Onboarding & Leaving
Part 4 · Questions 14–18
Cybersecurity
Part 5 · Questions 19–21
Backup, Recovery & Continuity
Plus
Six misconceptions & a provider scorecard
Written by
Matt Jones, President & CTO
Matt founded Freedom Tech in 2010. The guide is written to help you evaluate any IT provider, including us, so you can make a confident decision.
Read Matt's bioFree Instant Download
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