How to Evaluate Your Current IT Company Using a Simple 20-Point Checklist
← Back to Blog
Managed IT

How to Evaluate Your Current IT Company Using a Simple 20-Point Checklist

March 23, 20255 min readSteve Condit — Founder, Simply IT
Managed IT
How to Evaluate Your Current IT Company Using a Simple 20-Point Checklist

How do you know if your IT company is actually doing their job? Most business owners in Ocala and North Central Florida do not have the technical background to evaluate their IT provider's performance, and many IT companies take advantage of that knowledge gap. This 20-point checklist gives you specific, measurable questions to ask your current IT company. Their answers — or inability to answer — will tell you everything you need to know about the quality of service you are receiving.

20
Evaluation questions
20/20
Simply IT performs all monthly
0
Reports from most reactive IT
15 min
Simply IT avg response time
20-point IT company evaluation checklist for businesses
Use this 20-point checklist to evaluate whether your IT provider is delivering genuine managed services.
// Warning
Many IT companies market themselves as "managed service providers" while delivering reactive break-fix support with a monthly subscription wrapper. If your provider cannot answer these 20 questions, you are not receiving managed services regardless of what your contract says.

Monitoring (Questions 1-5)

MONITORING
✓
24/7 monitoring with dashboard proof
✓
Average response time data for 90 days
✓
Current device inventory on demand
✓
Hardware end-of-life plan
✓
Proactive fixes documented monthly

Security (Questions 6-10)

SECURITY
✓
MFA on all accounts
✓
Recent security risk assessment
✓
Current endpoint protection on all devices
✓
Security awareness training + phishing simulations
✓
Documented incident response plan

Patching (Questions 11-14)

PATCHING
✓
All workstations on supported OS with patches
✓
Critical patches within 24-48 hours
✓
Current firmware on network equipment
✓
Third-party application patching

Backup + Communication (Questions 15-20)

BACKUP + COMMUNICATION
✓
Backup tested with full restore
✓
Defined RTO and RPO
✓
Offsite/cloud backup separate from production
✓
Full environment rebuild capability
✓
Regular reporting on IT activities
✓
Strategic planning sessions for technology roadmap
DOWNLOAD THE FULL CHECKLIST
Get the printable version of this 20-point evaluation to use with your current IT provider.
Download Checklist →

Simply IT vs. Reactive IT Providers

CategoryReactive IT ProviderSimply IT
MonitoringNone24/7 with alerts
ReportsNeverMonthly detailed
Response TimeHours/days15 min average
Patch ManagementWhen requestedAutomated weekly
Backup TestingNever testedMonthly verified
Security ReviewsNoneQuarterly assessment
Strategic PlanningNoneQuarterly roadmap sessions
DocumentationMinimal/noneComplete and current

Scoring Your IT Company

ScoreRatingAction
18-20 answeredExcellentKeep your provider
15-17 answeredGood with gapsDiscuss improvements
10-14 answeredSignificant gapsConsider alternatives
Under 10Not managed servicesTime to switch
// Did You Know?
A genuine monthly IT report should include: devices monitored and their status, patches applied, security alerts and resolutions, backup verification results, tickets opened and resolved, and recommendations. If your report is a one-page summary with no specifics, it is a template — not a report.
"Documentation is proof of work. If your IT company cannot show you exactly what they did last month — what they monitored, patched, secured, and backed up — then for all practical purposes, they did not do it."
Simply IT

Simply IT is happy to walk through this checklist with any business owner in North Central Florida who wants an honest second opinion on their current IT situation.

Download the Free Network Assessment Checklist →
Steve Condit — Founder of Simply IT, Ocala FL
// Written By
STEVE CONDIT
Founder & Owner, Simply IT · US Marine Veteran · 30+ Years IT Experience

Steve Condit founded Simply IT to bring enterprise-grade IT management to small and mid-sized businesses across North Central Florida. With over 30 years of IT experience and a background in the US Marine Corps, Steve built Simply IT around the principle that local businesses deserve the same quality of technology partnership that large companies take for granted — without long-term contracts or national call center support.

// More From Managed IT

KEEP READING

Blog Article · Managed IT
Break-Fix vs. Managed IT for Florida Small Businesses — Which IT Model Actually Costs Less?
Break-fix IT support feels cheaper because you only pay when something breaks. But Florida small businesses that calculate the ...
July 8, 2026 · 8 min read
Read →
Blog Article · Managed IT
What's in a Managed IT Services Agreement? What Florida Small Businesses Need to Know
Most Florida small business owners sign a managed IT services agreement without fully understanding what they're committing to....
June 25, 2026 · 7 min read
Read →
Blog Article · Managed IT
IT Services for Gainesville Nonprofits — Microsoft 365 Nonprofit Pricing, Donor-Data Security & On-Call Support
Gainesville and Alachua County nonprofits run lean — tight budgets, heavy volunteer turnover, and donor data that has to stay p...
June 3, 2026 · 8 min read
Read →
// Continue Reading

RELATED SOLUTIONS & SERVICE AREAS

SolutionManaged IT Services →SolutionHelp Desk Support →Service AreaManaged IT in Ocala, FL →Service AreaManaged IT in Gainesville, FL →

READY TO SOLVE YOUR IT CHALLENGES?

Get a free technology assessment and find out exactly where your business stands.

Get a Free Assessment →See Our Pricing →