Questions to ask before hiring a managed service provider

The short answer: the seven questions that matter most

Before you hire a managed service provider, ask these seven questions and insist on specific answers: Who will actually be working on my computers? What exactly is included in the monthly fee, and what costs extra? What happens when I call with a problem? How do my backups work, and when did you last restore one? What security do you put on my computers and email, and what do you do when something gets through? What does the agreement say about leaving? And what do you know about businesses like mine?

Those questions sound basic. They are also the ones most people skip, because the sales conversation is usually about price and the provider is usually pleasant. The point of asking is not to catch anyone out. It is that a provider who answers clearly and in writing has thought about the work, and a provider who cannot answer will not be able to do the work either.

I answer all of these myself at the end of this article. You should hold me to the same standard you hold anyone else, and if you are comparing me to a larger company, the answers will look quite different, which is the point. Ask every provider the same list, write the answers down and compare them side by side. If you want a copy of the list to take into a meeting, ask me and I will send it.

Who will actually be working on my computers?

This is the first question because everything else depends on it. At a larger managed service provider the person who sells you the plan is not the person who fixes your printer, and the person who fixes your printer on Tuesday may not be the person who does it on Thursday. That is not wrong, but you should know it before you sign, and you should know how many people will have administrator access to your systems.

A good answer names a person or a small named group, explains how they learn your office, and explains what happens when that person is unavailable. Ask directly: if my main contact is on vacation, who covers, and do they know my setup? Ask how your documentation is kept, because the answer tells you whether the next technician will be starting from zero.

At Cross River Tech the answer is short. You deal with me, Anthony Omini. I do the assessment and the onboarding, I plan the work and I come onsite myself, and my team handles the routine monitoring, updates and day-to-day requests behind me, so nobody has to explain your setup twice and there is no ticket queue between you and the person who can fix things. The honest limits are that onsite visits are by appointment and that I work remote-first, because it is faster and cheaper for you. I keep full documentation of every office I support so that if you ever move on, the next provider gets a clean handover. I wrote more about that trade-off in a small owner-led IT company vs a big MSP.

What exactly is included, and what costs extra?

The monthly fee for managed IT should cover keeping what you have running. The disagreements start over what that means. Ask for the list of what is included and, more importantly, the list of what is excluded, in writing. If a provider only gives you the first list, ask again for the second.

A complete small-business plan in Dallas usually includes updates and patching, unlimited help desk support, antivirus and email security, managed backup, network management and documentation. The items that are most often left out or billed separately are:

• Onsite visits, or a cap on how many per month
• After-hours support, or a higher rate for it
• Servers, on per-user plans
• Projects such as migrations, moves and cabling
• Time spent on the phone with your software vendors
• Setting up new computers and new employees
• Microsoft 365 or Google Workspace licenses, which are normally passed through

None of these exclusions is unfair on its own. What matters is that you know about them before the invoice does. Ask for a sample invoice from a typical month if you want to see how the extras actually show up. I keep a full breakdown of what a good agreement contains in what a managed IT services agreement usually includes, and the pricing logic behind it in how much managed IT services cost in Dallas.

What happens when I call with a problem?

Do not ask for a response-time promise. Ask what actually happens. Where does the call go? Does a person answer, or a voicemail, or a ticket portal? Who decides whether your problem is urgent? How do you find out what is happening while you wait? What happens at 7 PM, or on a Saturday, or on a holiday?

A good answer describes a process you can picture. For example: you call a number, a person answers or calls you back, they connect to your computer remotely and fix it, and if it cannot be fixed remotely someone comes to the office. A weak answer is a number with no story attached, such as a promised number of minutes with no explanation of who is doing the responding.

Ask about remote support specifically, because that is how most problems get solved. Remote support means the technician connects to your screen over the internet, with your permission, and works on the problem while you watch. It is faster than a drive across Dallas and it is cheaper for you. A provider who insists on coming onsite for everything is billing you for windshield time.

Ask also about after-hours coverage. Remote support around the clock, including holidays, is something I offer, with after-hours rates applying for scheduled after-hours work. Whatever the provider says, get it in writing and make sure it distinguishes between an emergency you did not plan and an upgrade you would like done on a Sunday.

How do backups work, and when did you last restore one?

Backups are where the difference between a good provider and a poor one costs the most. Everyone says they do backups. The question that matters is whether anyone has ever restored from them.

Ask these, in this order: What is backed up, and what is not? Where does it go, and is there a copy away from the office? How often does it run? How long is data kept? When did you last do a test restore for a client, and how long did it take? What is your plan if the office floods, the server is stolen or ransomware encrypts everything?

A good answer covers servers, key workstations and cloud data. Many owners are surprised to learn that Microsoft 365 and Google Workspace do not back up your email and files in the way you assume; a deleted mailbox or a ransomware-encrypted OneDrive needs a separate backup to recover from fully. A good answer also includes a restore test on a schedule, not just when something breaks.

A bad answer is any version of it is all handled automatically. Automatic is fine; unverified is not. If the provider cannot tell you the date of their last test restore, assume there has not been one. My own approach is described on the cybersecurity, backup and disaster recovery page, and the short version is that I do test restores and I show you the result.

What does the agreement say about leaving?

You are asking this on the day you sign, which feels awkward, and it is still the most useful contract question there is. Ask: How long is the term? Does it renew automatically, and how much notice do I have to give to stop that? What does it cost to leave early? When I leave, what do I get back, and in what form? Who owns the passwords, the documentation, the domain name and the licenses?

The answers you want: a short term or none at all, no automatic renewal into another long term, no early-termination fee that looks like the rest of the contract, and a written commitment to hand over everything you own in a usable form. Ask specifically about administrator passwords for your firewall, your Microsoft 365 or Google Workspace tenant and your domain registrar, because those are the items that go missing most often when a relationship ends badly.

My agreement is month-to-month and you can cancel at any time. Everything about your systems is documented in your name, and if you leave you get the full documentation and every password the same week. I explain why I work this way, and when a longer contract can still make sense, in month-to-month vs annual IT contracts.

What do you know about businesses like mine?

General IT skill is necessary and not sufficient. A dental office needs someone who understands how practice management software talks to the imaging sensors and why HIPAA changes how backups and email have to be handled. A law firm needs someone who understands client confidentiality, document management and how court deadlines change what counts as urgent. An insurance agency has an agency management system and carrier portals that behave in their own particular ways.

Ask the provider to describe an office like yours that they support, in general terms, and to walk you through a problem they solved there. You are listening for familiarity with your software by name and with your working day: when your busy hours are, what stops the office cold and what can wait. You are not asking for client names, and a provider who volunteers them without permission is telling you how they will treat your name later.

I work mainly with law firms, dental and medical practices, insurance agencies and architecture and interior design firms in Dallas. The industries pages describe what I do differently for each. If your business is something else, I will tell you honestly whether I am a fit, because a mismatch costs you more than it costs me.

Red flags when choosing an IT support company

These are the signs that should make you slow down or walk away, regardless of how friendly the meeting was or how good the price looks:

1. They will not name who does the work. If you cannot find out who will have administrator access to your systems, you cannot evaluate them.
2. They will not list exclusions. A plan with no written exclusions has unwritten ones.
3. The contract is long, auto-renews and is expensive to leave. A three-year agreement is a bet that the service will be good in month thirty. You have no way to know that on day one.
4. They cannot tell you when they last restored a backup. Untested backups are a hope, not a plan.
5. They promise you will never have downtime or that you will be fully compliant. Nobody can promise either. The honest wording is that they help you meet the requirements.
6. They want to replace everything on day one. Some equipment does need replacing. A provider who cannot tell you why each item has to go, in plain words, is selling hardware.
7. They talk down to you. If the explanation is jargon and the tone is impatient in the sales meeting, imagine the support call.
8. They have no answer for after hours. Problems do not keep office hours. There should be a plan, even if it costs extra.
9. They will not give you the passwords. Anything they set up in your business should be documented in your name. A provider who keeps the keys is planning for the day you try to leave.
10. The price is far below the market. Small-business managed IT in Dallas is commonly quoted around $100 to $175 per user per month. A quote at half that is missing something, and you will find out what when it breaks.

None of these is proof of a bad provider on its own. Two or three together are.

How I answer these questions myself

Since I am asking you to put every provider through the same questions, here are my answers, in the same order, so you can compare directly.

Who does the work? I do, Anthony Omini, with over 15 years of IT experience across many industries and global organizations. I am your point of contact from the assessment onward, and my team handles the routine monitoring and updates behind me. What is included? Updates for computers and servers, unlimited remote support, onsite visits at no extra charge when remote cannot fix it, antivirus and email security, managed backup and disaster recovery, and management of your internet, firewall, switches, access points and printers. Excluded and quoted separately: hardware, licenses and projects such as moves, migrations and cabling. What happens when you call? You call (214) 612-7080; I answer or call you back, connect remotely and fix it, and come onsite by appointment if remote cannot. Remote support is available around the clock including holidays; after-hours rates apply for scheduled after-hours work. Backups? Servers, key workstations and Microsoft 365 or Google Workspace data, with a copy off-site and scheduled test restores I show you. Leaving? Month-to-month, cancel anytime, full documentation and every password handed over. Businesses like yours? Law firms, dental and medical practices, insurance agencies and design firms across the Dallas–Fort Worth area, remote-first anywhere in Texas.

The one answer I cannot give is a response-time promise, because I would rather tell you how it actually works than print a number. If those answers sound like the kind of IT support you want, get in touch and I will put them in writing for your office. The managed IT services page has the full scope.

Questions people ask

Written and reviewed by

Anthony Omini, founder of Cross River Tech

Over 15 years in IT across many industries, now running Cross River Tech, a small owner-led managed IT company in Dallas. Every article is written from his own client work and checked by him before it is published.

Ask me the same questions Bring the list. I will answer every one in writing for your office, including the ones about leaving.

Ask Anthony(214) 612-7080About Anthony