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

May 9, 20235 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
VIDEO COMING SOON
Simply IT — Evaluating Your IT Company — Simply IT Assessment

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.

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