20 Questions to Ask an IT Support Company
Most IT support companies sound alike on a first call. Everyone offers help desk support, security and monitoring. Everyone says they’re proactive. The differences only show up when you ask specific questions and listen closely to the answers.
The most important questions to ask an IT support company are these: How do employees request help, and how is it tracked? What’s included, and what’s billed separately? What security standard do you build on? How often are backup restores tested? Who owns our admin access and documentation? How do you plan with us? What happens if we leave?
The 20 Questions at a Glance
Here is why each question matters and what a strong answer sounds like.
Questions About Fit and Experience
1. Who is your typical client?
Why it matters: A provider built around 10-person offices works differently from one built around 300-person companies. You want to be in the range they serve every day.
A strong answer: A clear description of company size, industries and the kind of IT setup they usually support.
2. Do you support businesses like ours and the software we use?
Why it matters: Industry experience matters less than familiarity with how you work. A law firm’s document management system or a manufacturer’s production scheduling tools are what your team depends on.
A strong answer: Specific examples of similar businesses or the same software. They should also be willing to say, “we haven’t worked with that platform, and here’s how we’d approach it.”
3. Can we speak with a current client?
Why it matters: A reference call tells you more than any website. Ask the reference what happened the last time something went wrong.
A strong answer: A yes, with a client similar to you in size or industry.
Questions About Day-to-Day Support
4. How do our employees request help, and how are requests tracked?
Why it matters: If requests go to one technician’s cell phone, nothing is tracked and nothing is covered when that person is out.
A strong answer: Defined channels, such as a client portal, a support email address and a business phone number. Every request should be logged, so you can see its status and history.
5. How do you prioritize issues, and what do you commit to in writing?
Why it matters: “We’re fast” isn’t a commitment. You want to know how an outage affecting the whole office is treated differently from one employee’s printer problem, and what the agreement actually says.
A strong answer: An explanation of priority levels and what the agreement commits to for each. Be thoughtful about any promise that sounds absolute. Nobody can honestly guarantee a fix time for every possible issue, and a provider who explains that is being straight with you.
6. What happens when an issue is beyond the first person who handles it?
Why it matters: Complex problems need senior engineers. You want to know how an issue moves up, and who owns it once it does.
A strong answer: A clear escalation path, and a named person or team responsible for your account on bigger issues.
7. What is handled remotely, and when do you come onsite?
Why it matters: Most support happens remotely, but hardware, network and office projects often need someone in the room.
A strong answer: A plain explanation of when onsite visits happen, the area they cover, and whether visits are included or billed separately.
8. What coverage do we have outside business hours?
Why it matters: If your team works evenings or weekends, or your systems need to run overnight, you need to know what happens when something breaks at 9 p.m.
A strong answer: A specific description of what after-hours coverage includes, which issues it covers, and how to reach it. Vague reassurance isn’t enough. Ask to see it in the agreement.
Questions About Security and Backup
9. What security standard do you build your services around?
Why it matters: Security added one product at a time leaves gaps. A recognized framework gives you a defined baseline and a way to check what’s in place.
A strong answer: The name of a real framework, such as the CIS Controls, and an explanation of what it means in practice for your business. Be careful with any answer that promises you can’t be breached or that you’ll automatically be compliant. Good security reduces risk. It doesn’t remove it.
10. How do you handle backups, and how often are restores tested?
Why it matters: A backup only matters if you can restore from it. Many businesses find out their backups don’t work at the worst possible moment.
A strong answer: Where backups are stored, which systems are covered, how often restores are tested, and how you see the results.
11. What happens if we have a security incident?
Why it matters: An incident is the moment you find out whether your provider has a plan. You want to know that before it happens.
A strong answer: A clear description of their incident process: who responds, how you’re informed, and what is included in the agreement versus billed as additional work.
Questions About Planning and Honesty
12. Who helps us plan, and how often do we meet?
Why it matters: Support keeps things running today. Planning keeps you from being surprised by aging hardware, expiring licenses or budget shocks next year.
A strong answer: A named person responsible for planning, a regular meeting schedule, and a written roadmap tied to your business goals.
13. Can you tell me about a time you advised a client not to buy something?
Why it matters: This is the most revealing question on the list. It tells you whether recommendations are driven by your needs or by what’s easy to sell.
A strong answer: A specific story. If they can’t think of one, that tells you something too.
Questions About Pricing and Contracts
14. What is included, and what is billed separately?
Why it matters: Two quotes can look similar and cover very different work. Projects, onsite visits, new equipment setup and after-hours work are common areas where agreements differ.
A strong answer: A written list of what the monthly agreement covers and what counts as separate project work, with examples.
15. How is pricing calculated?
Why it matters: Agreements are commonly priced per user, per device, or a mix of both. The model affects how your costs change as you grow.
A strong answer: A plain explanation of their pricing model, and what happens to your cost when you add or remove people. Our managed IT services pricing guide explains the common models in more detail.
16. What are the contract term, notice period and renewal terms?
Why it matters: Auto-renewal clauses and long notice periods catch a lot of businesses off guard.
A strong answer: Clear terms, stated up front, with no surprises in the fine print.
17. What happens if we decide to leave?
Why it matters: It may feel odd to ask about the exit before you’ve started, but the answer shows how a provider thinks about your ownership of your own systems.
A strong answer: A defined offboarding process, including handover of credentials, documentation and licenses, and a clear statement of whether that work is billed. If you’re leaving a provider now, our guide on how to switch IT providers covers the process step by step.
Questions About Ownership and Accountability
18. Who owns our admin access, documentation and licenses?
Why it matters: Your systems and data belong to your business. You should always be able to access them, whoever manages them.
A strong answer: Your business keeps admin access and copies of documentation. You know exactly which licenses are billed through the provider and how they would transfer if you left.
19. How do you handle your own mistakes?
Why it matters: Every IT team makes mistakes eventually. What matters is whether they tell you, fix it, and make sure it doesn’t happen again.
A strong answer: A direct answer that includes an example. A provider who claims they never make mistakes isn’t being realistic.
The Partnership Question
20. What do you need from us for this to work?
Why it matters: A good IT relationship has commitments on both sides. A provider who only talks about what they’ll do is describing a vendor, not a partner.
A strong answer: A specific list. That might include being open about problems, giving them timely access, involving them before technology decisions, and being willing to invest where it’s needed.
Questions a Good IT Support Company Will Ask You
The first conversation should go both ways. A provider who wants to understand your business before quoting will usually ask things like:
- How many people do you have, and how many locations?
- What software does your team rely on every day?
- What is frustrating people about technology right now?
- Do you have anyone internally who handles IT?
- When does your current contract end?
- Where do you see the business in two or three years?
If a provider sends a price without asking questions like these, the quote is based on assumptions, not on your business.
IT Support Company Evaluation Scorecard
Use this table to compare providers after your calls.
| Area | A strong answer | Worth probing |
|---|---|---|
| Support process | Defined channels, every request tracked | Support through one person's phone |
| Priorities and commitments | Clear priority levels, commitments in writing | Absolute promises with no written terms |
| Escalation | Named owner for complex issues | "We'll figure it out" |
| Security | A named framework with practical detail | Product lists with no plan behind them |
| Backup | Regular restore testing with visible results | "Backups run every night" with no testing |
| Planning | Scheduled reviews and a written roadmap | Planning only when you ask |
| Honesty | A real story about advising against a purchase | No example |
| Pricing | A written scope and a clear model | Vague "it depends" with no examples |
| Exit terms | A defined offboarding process | Reluctance to discuss leaving |
| Ownership | Your business keeps access and documentation | The provider holds everything |
| Accountability | Owns mistakes openly | Claims mistakes don't happen |
| Partnership | Clear expectations on both sides | Only talks about what they deliver |
If You Already Have Internal IT Staff
If you have an IT person or team, you are probably looking at co-managed IT. Add these questions:
- How do we divide responsibilities, and where is that written down?
- Will both teams work from the same documentation and ticketing system?
- How is admin access shared and logged?
- How do issues move between our team and yours?
Our guide to co-managed IT vs managed IT explains how the two models differ and how to choose.
How Datastrive Answers These Questions
We think any provider you’re considering should answer this list openly, so here are our answers to the key ones.
How employees get help: Through our client portal, by email at [email protected], or by phone at (773) 863-3868. Every request is tracked and handled by the whole team, not one person’s phone.
Security standard: Every agreement is built around the CIS Controls v8.1 framework, with Implementation Group 1 as the minimum for every business we work with. We describe what’s in place and why. We don’t promise outcomes no framework can guarantee.
Pricing: After reviewing your setup, you get a written plan in plain numbers showing what we recommend, what we don’t think you need, and what it costs.
Advising against purchases: We treat your money like it’s ours. If something isn’t worth the cost for your business right now, we’ll tell you.
Mistakes: When we’re responsible, we say so, fix it, and keep you updated. You shouldn’t have to chase us.
What we need from you: Treat our team as an extension of yours, be open and honest with us, be willing to invest in technology where it matters, and ask us for lots of help.
You can read more on our Why Datastrive page or learn about our managed IT services in Chicago.
Frequently Asked Questions
How many IT support companies should we talk to?
Two or three is usually enough to compare approaches without the process dragging on. Ask each one the same questions so the answers are easy to compare.
Should we ask about response times?
Yes. Ask how issues are prioritized, what the agreement commits to, and how performance is reported. Look for commitments that are specific and written down, rather than promises that sound impressive but aren’t in the contract.
Does it matter if the IT company is local?
It depends on how often you need onsite help. Remote support covers most day-to-day issues, but hardware, network work and office projects go more smoothly when the team can easily get to your office.
What certifications should an IT support company have?
Vendor partnerships and technical certifications can show that a team keeps its knowledge current. Ask what a certification means for your environment specifically, rather than treating a list of logos as proof of quality.
What is the biggest red flag when choosing an IT support company?
A provider who can’t clearly explain what you’re paying for, or who is reluctant to give you access to your own systems. Both usually lead to bigger problems later.
Should we ask these questions of our current provider too?
Yes. The same questions work as a check-up on an existing relationship. The answers may confirm you’re in good hands, or show you where to push for improvements.
Ask the Hard Questions Before You Sign
The right IT support company won’t mind a long list of questions. Clear answers are part of how a good partnership starts. If you’d like to hear how we’d answer them for your business, we’re happy to talk.