Most IT proposals are impossible to compare. Two providers quote a monthly number, both say “fully managed,” and neither document tells you what happens when your server dies on a Saturday. The pricing looks like the only variable, so people pick on price and find out what they bought eight months later.

These are the nine questions we would ask in your position. They are ordered roughly by how much money the answer can cost you.

1. What is the exit? Specifically.

Ask for the offboarding clause and read it before you read anything else. You want a stated notice period you can live with, and a written commitment that you get your data, your documentation, your license ownership, and your administrator passwords back on the way out.

Providers who hold the domain registration, the Microsoft tenant, or the firewall admin account in their own name can make leaving cost more than staying. That arrangement is common and it is not an accident.

2. What is included, and what will you bill me for?

Ask for the line between the two in writing, with examples. “Fully managed” is not a scope. A useful answer names specific work on both sides: new-employee setup included, physical cabling billable, that sort of thing.

If the answer is vague here, every surprise invoice you receive for the next three years starts in this paragraph.

3. Who answers when I call, and what happens in the first hour?

The relevant questions are: does a human respond or does a ticket number respond, what is the committed time to a first reply during business hours, and what happens at 9pm. Ask for their actual median response time last quarter, not the number in the contract. Any provider measuring themselves can produce it in a minute.

4. Is the help desk in-house or subcontracted?

There is nothing wrong with a subcontracted after-hours desk, provided you know that is what you are buying and the handoff is documented. What you do not want is to discover during an outage that the person on the phone has no access to your systems and no idea what you run.

5. When did you last restore one of my kind of systems from backup?

Not “do you do backups.” Everyone does backups. Ask when they last performed a full restore, how long it took, and whether they will show you a report from it. A provider who runs restore drills will be pleased you asked. A provider who does not will change the subject to their backup software’s brand name.

6. How do you handle an employee leaving on the same day?

This is a small question that reveals process. Same-day departures are the most common real security event at a small business. Ask what their procedure is, how fast it runs, who can trigger it, and whether it covers email, file access, phone system, VPN, and the applications you actually use, including the ones they did not set up.

7. What do you do about the things that keep breaking?

A provider paid per ticket has no reason to make tickets stop. A provider paid monthly does. Ask what recurring problem they eliminated for a client last quarter and how. If the honest answer is “we close a lot of tickets fast,” you have learned something useful about the incentive you are signing up for.

8. Who will actually be at my office, and how many other clients do they have?

You want the name of an engineer, an idea of their workload, and a plan for what happens when that person is on vacation. Ask how documentation is kept so the second engineer is not starting from zero. Small providers win on this question and then lose on it during the one week their senior person is out.

9. What will you refuse to sell me?

Our favorite question, and the one that gets the most revealing answers. Every provider has products with better margins than others. Ask them to name something they routinely talk clients out of. A provider who cannot think of a single thing is selling the catalog.

Ask us these too

We wrote our own answers down where you can check them: the scope table says what the monthly fee covers and what we bill separately, the response numbers are the ones we hold ourselves to, and the security page includes a section on what we will not sell you.

If you are evaluating providers right now, including providers who are not us, take this list into the meeting. Good ones will enjoy it.

Nine questions to ask an IT provider before you sign