The last IT support company I worked with had a great sales pitch. Fast response times, proactive monitoring, “we treat your business like our own.” Three months in, a server issue took 14 hours to resolve because their “24/7 support” turned out to be an after-hours answering service that emailed a ticket to someone who checked it in the morning. Proactive monitoring? They didn’t even know the server was down until I called them.
Bad IT support doesn’t just cost money. It costs productivity, customer trust, and your sanity. When your systems go down and your provider can’t get you back online quickly, every employee is sitting idle, every customer interaction is stalled, and you’re burning money by the hour.
Good IT support, on the other hand, is invisible. Things just work. Problems get caught before they become outages. Updates happen in the background. And when something does break, it gets fixed fast by someone who already knows your systems. These 15 questions will help you tell the difference before you sign a contract.
Before You Start Talking to IT Companies
Do some homework before you pick up the phone. It’ll make you a more informed buyer and help you spot empty promises.
- Inventory your current technology. Desktops, laptops, servers, network equipment, printers, phones, cloud services. How many devices? What operating systems? What business-critical applications? An IT company needs this information to give you an accurate quote.
- Identify your pain points. Slow computers? Frequent downtime? Security concerns? Difficulty onboarding new employees? Knowing your problems helps you evaluate whether a provider can actually solve them.
- Define your expectations for response time. What’s acceptable when a system goes down during business hours? 15 minutes? An hour? Four hours? Your expectations need to match what the provider offers.
- Know your compliance requirements. HIPAA, PCI DSS, SOX, CMMC, or state privacy laws. If you have compliance obligations, you need an IT provider with specific experience in that area.
- Set a budget range. Managed IT services for small businesses typically run $100 to $300 per user per month. Know your ceiling before comparing proposals.
What to Mention or Send Beforehand
When reaching out to IT support companies, share these details so they can prepare a relevant proposal:
- Your business size (number of employees, locations, remote workers)
- A list of your current devices, servers, and primary software
- Your current IT setup (in-house IT person, break-fix provider, or nothing)
- Any recent IT issues or ongoing problems
- Your compliance and security requirements
- Whether you need help with a specific project (office move, cloud migration) in addition to ongoing support
Response Time and Support Quality
1. What are your guaranteed response times, and how are they enforced?
Response time is the most important metric in IT support. When your email goes down or your point-of-sale system crashes, every minute matters. A response time SLA (Service Level Agreement) should specify: how quickly they acknowledge the issue, how quickly a technician begins working on it, and the maximum time to resolution for different severity levels.
Get the numbers in writing. “We respond quickly” isn’t an SLA. “Critical issues acknowledged within 15 minutes, technician assigned within 30 minutes, and resolution within 4 hours” is an SLA. Also ask what happens when they miss the target. Account credits? Escalation? Or just an apology?
2. What does “24/7 support” actually mean, and who answers at 2 a.m.?
This is where the gap between marketing and reality is widest. Some providers have fully staffed operations around the clock. Others have an answering service that creates a ticket for the morning shift. A few have an on-call technician who may or may not answer their phone.
Ask specifically: Is after-hours support provided by in-house technicians or outsourced to a call center? Can after-hours staff actually fix problems remotely, or can they only log tickets? Is there a separate charge for after-hours support? What’s the average after-hours response time based on actual data, not the target?
3. How do you handle escalation when an issue isn’t resolved quickly?
Level 1 support handles basic issues: password resets, printer problems, software questions. When an issue exceeds their skills, it should escalate to Level 2 or Level 3 engineers with deeper expertise. The question is: how fast does escalation happen, and is there a clear process?
Ask for their escalation matrix. How long does Level 1 work on an issue before escalating? Who makes the escalation decision? Is there an automatic escalation trigger (for example, any ticket open for more than two hours escalates automatically)? Slow escalation is one of the most common complaints about IT support. The technician keeps trying instead of admitting they need help, and hours pass.
Pricing and Contracts
4. How is pricing structured, and what’s included?
IT support pricing falls into three main models:
Per-user pricing ($100 to $300/user/month): Covers everything for each employee regardless of how many devices they use. Simple and predictable.
Per-device pricing ($50 to $150/device/month): Charges based on the number of devices managed. Can be cheaper for businesses with few devices per employee.
Flat-rate/all-inclusive ($1,000 to $5,000+/month): A fixed monthly fee covering everything. Best for predictable budgeting.
For any model, ask specifically what’s included and what costs extra. Common add-on charges that surprise people: after-hours support, on-site visits, new equipment setup, cloud migration, security assessments, and project work (network upgrades, office moves). Get a sample invoice from a comparable client so you can see what a typical month actually costs.
5. What is the contract length, and what’s the exit clause?
One-year contracts are standard. Three-year contracts are common but risky unless you’ve worked with the provider before. Month-to-month is ideal for testing but often comes at a premium.
Read the exit clause carefully. What’s the notice period (30, 60, or 90 days)? Are there early termination fees? What happens to your data and documentation when you leave? A good IT provider hands over complete documentation of your systems, passwords, and configurations. A bad one holds your information hostage.
Proactive vs. Reactive Support
6. What proactive monitoring and maintenance do you perform?
The difference between good IT support and mediocre IT support comes down to this question. Reactive support waits for you to call with a problem. Proactive support catches problems before you notice them.
Proactive services should include: 24/7 monitoring of servers, workstations, and network equipment for hardware failures, performance issues, and security threats. Automated patch management for operating systems and applications. Regular health checks and maintenance. Disk space and backup monitoring. The goal is fewer emergency calls, not just faster responses to them.
7. How do you handle software updates and patch management?
Unpatched software is the most exploited attack vector. But indiscriminate patching can break things. A good IT provider tests patches before deploying them, schedules updates during off-hours to minimize disruption, and has a rollback plan when an update causes problems.
Ask: How quickly are critical security patches applied after release? Are updates tested in a staging environment before pushing to production? Can we schedule maintenance windows that don’t overlap with our business-critical hours? Who takes responsibility if a patch breaks something?
Security and Compliance
8. What is your approach to cybersecurity for our business?
IT support and cybersecurity are deeply intertwined. Your IT provider should be your first line of defense, not just the people who reset passwords and fix printers.
A comprehensive approach includes: endpoint protection (antivirus/EDR) on all devices, email security and spam filtering, firewall management, MFA enforcement, regular vulnerability scanning, employee security awareness training, and incident response planning. If the provider says “we install antivirus and call it good,” they’re not providing modern security. Ensure you have a UPS battery backup on critical systems so your equipment stays protected during power events, giving your IT provider time to manage shutdowns properly.
9. Do you have experience with our specific compliance requirements?
If you’re in healthcare (HIPAA), handle credit card data (PCI DSS), work with government contracts (CMMC), or serve EU customers (GDPR), your IT provider needs to understand and support those frameworks. Not “we can figure it out.” They need demonstrable experience.
Ask for references from clients in your industry with similar compliance needs. Ask about their compliance documentation process, audit support capabilities, and whether they’ll take contractual responsibility for maintaining the technical controls required by your compliance framework. A provider who doesn’t understand your compliance needs can put your business at legal risk.
Onboarding, Documentation, and Communication
10. What does the onboarding process look like, and how long does it take?
Transitioning to a new IT provider is a significant undertaking. A professional onboarding process should include: a full audit of your current environment (hardware, software, network, security posture), documentation of all systems, accounts, and configurations, transition of monitoring and management tools, setup of their help desk and ticketing system for your team, and a kickoff meeting to align on expectations and processes.
Ask for a typical onboarding timeline. Two to four weeks is reasonable for a small business. If they say “we’ll have you up and running by Friday” for a 50-person company, they’re either cutting corners or underestimating the work.
11. How do you document our systems, and do we own that documentation?
Documentation is one of the most overlooked aspects of IT support, and it’s one of the most valuable. Proper documentation includes: network diagrams, hardware inventory, software licenses, admin credentials (stored securely), vendor contacts, standard operating procedures, and configuration details for every system.
The critical question: do you own this documentation? If your IT provider is the only one who knows how your network is configured and they hold the passwords, you’re dependent on them in a way that can become very uncomfortable during a contract dispute or transition. Insist on documentation that belongs to you and is accessible to you at all times.
12. How will you communicate with us, and who is our main point of contact?
You don’t want to explain your business to a different technician every time you call. A dedicated account manager or primary contact who knows your environment saves time and reduces miscommunication.
Ask about: your primary point of contact for strategic discussions and escalations, how tickets are submitted and tracked (phone, email, portal), reporting frequency (monthly reviews with metrics), and how they communicate during major incidents (real-time updates or radio silence until it’s fixed). Monthly or quarterly business reviews where the provider walks through performance metrics, upcoming issues, and strategic recommendations are a hallmark of quality managed IT.
Scalability and Strategic Value
13. Can you support our growth, including new locations, remote workers, and cloud migration?
Your IT needs today aren’t your IT needs in two years. If you’re planning to open a second office, shift to remote work, migrate to the cloud, or double your headcount, your IT provider needs to support that growth without missing a beat.
Ask about their experience with: multi-site networking, VPN and remote access solutions, cloud migration (Microsoft 365, Google Workspace, Azure, AWS), scaling from 20 users to 100 users, and supporting a hybrid workforce. A provider that’s great for a 10-person office but has never managed a multi-location environment won’t scale with you.
14. Do you offer strategic IT planning, or just break-fix support?
The best IT support companies aren’t just fixing what breaks. They’re helping you plan technology investments, avoid costly mistakes, and align your IT strategy with your business goals.
Ask whether they provide: annual technology roadmap planning, hardware lifecycle management (planning replacements before failures), budget forecasting for upcoming IT needs, vendor management (negotiating with software and hardware vendors on your behalf), and recommendations for improving efficiency and reducing costs. If all they do is answer the phone when something breaks, you’re paying for a technician, not a technology partner. You want a partner. Keep your own workspace organized with proper cable management to reduce the clutter that makes troubleshooting harder.
15. Can I speak with two or three current clients in a similar industry and size?
References are the best reality check available to you. Any provider who hesitates when you ask for references is hiding something. Ask for clients in your size range and industry, then actually call them.
Questions for references: How responsive are they when something breaks? Have they ever missed an SLA commitment? How was the onboarding experience? Do they proactively identify and fix issues? Would you hire them again? The answers from actual clients are worth more than anything on the provider’s website.
Typical Cost Range and Factors
Here’s what managed IT support typically costs for small to mid-sized businesses in 2026:
Per-user pricing: $100 to $300 per user per month. Covers all devices per user, help desk, monitoring, security basics, and standard maintenance. Most common pricing model.
Per-device pricing: $50 to $150 per device per month. Separate fee for each desktop, laptop, server, and network device. Can be cheaper for businesses where employees have only one device.
Server management (add-on): $200 to $500+ per server per month. On-premises servers require additional monitoring, backup, and maintenance beyond standard per-user pricing.
Project work (one-time): Billed hourly ($125 to $250/hour) or as a flat project fee. Covers office moves, network overhauls, cloud migrations, and new system deployments. Not typically included in monthly managed services.
What affects pricing:
- Number of users/devices is the primary cost driver
- Complexity (multiple locations, compliance requirements, on-premises servers) increases cost
- Service level (business hours only vs. 24/7, basic vs. premium support tiers)
- Security requirements (basic endpoint protection vs. full security stack)
- Industry compliance (HIPAA, PCI add specialized requirements and cost)
- Geographic location (metro areas cost more than rural areas)
For a 25-person company on a mid-tier plan, expect $3,000 to $5,000 per month for comprehensive managed IT support.
Red Flags vs. Green Flags
| Red Flag | Green Flag |
|---|---|
| No written SLA with specific response time commitments | Detailed SLA with response and resolution targets by severity level |
| ”24/7 support” that’s actually an answering service after hours | In-house technicians available around the clock who can resolve issues remotely |
| No proactive monitoring; they wait for you to report problems | Automated monitoring with alerts that catch issues before you notice them |
| Won’t provide references or provides only hand-picked testimonials | Readily provides 2-3 references from clients in your industry and size range |
| Documentation of your systems belongs to them, not you | Complete documentation that you own and can access at any time |
| Long-term contract with no exit clause or heavy termination fees | Reasonable contract with clear exit provisions and 30 to 60 day notice period |
| No security beyond basic antivirus | Comprehensive security approach including MFA, patching, monitoring, and training |
| Different technician every time with no continuity | Dedicated account manager and consistent team who know your environment |
Money-Saving Tips
- Get at least three proposals and compare them line by line. IT support pricing varies significantly. Three proposals reveal the market rate for your area and size, and they expose providers who are padding their quotes.
- Start with the essentials and add services as needed. Basic monitoring, help desk, and security can be a starting package. Add advanced services (security assessments, strategic planning, compliance support) when the value is clear.
- Ask about discounts for annual prepayment. Many providers offer 5 to 15% discounts for paying annually instead of monthly. On a $4,000/month contract, that’s $2,400 to $7,200 saved per year.
- Bundle services with one provider. Using one company for IT support, cybersecurity, cloud management, and backup is almost always cheaper than using separate vendors for each.
- Negotiate project work rates upfront. If you know you’ll need a cloud migration or network upgrade, negotiate the hourly rate or project fee during contract negotiation when you have the most leverage.
- Use the provider’s volume purchasing for hardware and software. IT providers often get better pricing on equipment and licenses than you can get on your own. A quality ethernet cable costs less through bulk purchasing, and enterprise software licenses through a provider can save 10 to 30%.
Glossary
SLA (Service Level Agreement): A formal contract between you and your IT provider that specifies performance metrics, response times, resolution targets, and consequences for failing to meet those targets. The SLA is the foundation of accountability in a managed IT relationship.
MSP (Managed Service Provider): A company that remotely manages and monitors your IT infrastructure and systems for a recurring fee. MSPs provide proactive support (catching problems early) versus break-fix providers who only respond when something is already broken.
RMM (Remote Monitoring and Management): Software used by IT providers to monitor the health and performance of your devices and servers remotely. RMM tools detect issues like failing hard drives, high CPU usage, and missed backups before they cause outages.
EDR (Endpoint Detection and Response): Advanced security software for individual devices that goes beyond traditional antivirus. EDR monitors behavior patterns, detects sophisticated threats, and can automatically isolate a compromised device from the network to prevent spread.
ITIL (Information Technology Infrastructure Library): A framework of best practices for IT service management. IT providers that follow ITIL standards typically have more mature, consistent, and reliable service delivery processes.
Ticket/Ticketing System: A system for tracking IT support requests from submission to resolution. Each issue gets a unique ticket number with a timeline of actions taken. Good ticketing systems provide transparency, accountability, and data for measuring performance.
Helpful Tools and Resources
Protects servers and workstations from power surges and outages. Gives your IT provider time to perform clean shutdowns during power events, preventing data corruption and hardware damage.
A wired connection is faster, more reliable, and more secure than Wi-Fi for workstations and servers. Quality Cat6 cables support gigabit speeds and reduce the network issues your IT provider would otherwise troubleshoot.
Tangled cables behind desks and in server areas slow down troubleshooting and create safety hazards. A $20 cable management kit saves your IT provider time (and saves you billable hours) on every on-site visit.
- CompTIA MSP Partner Program: CompTIA’s directory helps you find IT providers with verified certifications and training. A CompTIA-certified MSP meets documented standards for technical competency.
- Clutch.co IT Services Reviews: Independent reviews of managed IT providers with detailed project information, pricing data, and client testimonials.
- Better Business Bureau (BBB): Check complaint history and ratings for any IT support company before signing a contract. Look for patterns in complaints, not just the overall rating.
Quick Reference Checklist
Use this when evaluating IT support companies:
- What are the guaranteed response times for different severity levels?
- What does “24/7 support” actually mean (in-house techs or answering service)?
- How does escalation work when Level 1 can’t resolve the issue?
- How is pricing structured, and what’s included vs. extra?
- What is the contract length and exit clause?
- What proactive monitoring and maintenance is performed?
- How are software updates and patches managed?
- What cybersecurity measures are included?
- Do they have experience with our compliance requirements?
- What does the onboarding process look like?
- How is our environment documented, and do we own the documentation?
- Who is our primary point of contact?
- Can they support growth (new offices, remote workers, cloud)?
- Do they offer strategic IT planning or just break-fix?
- Can I speak with 2-3 current client references?
Frequently Asked Questions
What’s the difference between break-fix IT and managed IT services?
Break-fix means you call when something breaks, and you pay by the hour for the repair. Managed IT means you pay a monthly fee for proactive monitoring, maintenance, and support. Break-fix is cheaper when everything works, but expensive and unpredictable when things go wrong. Managed IT is a consistent monthly cost that prioritizes prevention. For most businesses, managed IT is the better value because it reduces downtime and catches problems early.
How many IT support companies should I get proposals from?
Three is the sweet spot. It gives you a clear picture of the market rate, helps you identify outliers (both too cheap and too expensive), and gives you negotiating leverage. Make sure each provider is quoting on the same scope of services so you’re comparing apples to apples.
Can a small business manage IT without an outside provider?
If you have fewer than 10 employees, simple technology needs, and no compliance requirements, one tech-savvy person wearing multiple hats can work. But it’s risky. That person doesn’t have 24/7 coverage, may not have deep security expertise, and is a single point of failure. Most businesses with 10+ employees benefit significantly from professional IT support.
Should I choose a local IT company or a national provider?
For businesses that need on-site support (server rooms, network infrastructure, hardware issues), a local provider with reasonable drive time is important. For fully cloud-based businesses with remote teams, geography matters less. The ideal provider has local presence for on-site needs and remote capabilities for everything else. Ask about their average on-site response time for your location.
How do I transition smoothly from one IT provider to another?
Give proper notice per your contract (30 to 90 days). Demand complete documentation of your systems, passwords, and configurations from the outgoing provider. Have the new provider perform an audit before the transition date. Plan for a two to four week overlap period where both providers have access. And never let your IT documentation be held by only one party.