The best way to compare IT support companies is to ask the same questions to each and listen carefully to the answers. Here are the questions we recommend Boca Raton businesses ask, and what a good answer sounds like.
Support and Response
1. Who answers when my team calls? Look for a real help desk with trained technicians and tracked tickets, not a voicemail box or one person’s cell phone.
2. How quickly do you respond? A good provider has defined response targets by priority and puts them in writing. An office-wide outage should be treated very differently from a single printer issue.
3. What happens after hours? Ask what is monitored around the clock, how emergencies are handled at night and whether a 24/7 help desk is available if you need it.
4. When do you come on-site? Most issues are fixed remotely. Ask how on-site visits are scheduled and how far away the team is.
Security and Backups
5. What security is included? Antivirus alone is not enough. Look for endpoint detection and response, 24/7 security monitoring, email security, multi-factor authentication and staff training.
6. How do you know our backups work? The right answer involves regular restore tests and reports, not just confirmation that backup jobs ran.
7. What would you do if we were hit by ransomware? Listen for a clear plan: containing the threat, involving your insurer, restoring from protected backups and fixing how it happened.
Pricing and Agreement
8. What is included in the monthly price? Ask for a written list of what is included and what is billed separately, such as projects and new equipment.
9. How long is the agreement, and how does it end? You should understand the term and the exit process before you sign.
10. Who owns our documentation and passwords? They should belong to you and be handed over if you ever leave.
Planning and Partnership
11. How do you help us plan? Look for regular reviews that cover risks, priorities and budget, not only ticket counts.
12. Can I speak with clients like us? Confident providers are happy to share references.
Listen for Specifics
Vague answers, promises that you will never be hacked or reluctance to put scope in writing are warning signs. Specific, honest answers usually point to a provider you can trust. Ask us these questions, or learn more about IT support in Boca Raton.
Managed IT & Help Desk →
Proactive monitoring, maintenance and a responsive help desk, with every system documented and every vendor managed.
“I have worked with Simplitfy & Erick Solms for many years on different projects and have always been pleased with the attention to detail and response we receive when in crisis. (when you need IT it's always a crisis!)”
Frequently Asked Questions
What is the most important question to ask an IT company?
Ask how they handle security and how they prove backups work. Those answers show how seriously they protect your business.
Should an IT company guarantee we will never be hacked?
No honest provider can promise that. Look for layered security, monitoring, tested backups and a clear incident response plan.
What should we ask references?
Ask how quickly issues are resolved, how well the provider communicates and how they handled a problem or mistake.
Last updated November 2026