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Twelve Questions to Ask an IT Provider Before You Sign Anything

The right questions to ask an IT provider are the ones a bad provider answers vaguely. Here are twelve, what a good answer sounds like, and the replies to walk away from.

By Squish··4 min read

Most people choosing an IT provider are being asked to judge work they cannot see, in language they were never taught, against competitors who all sound roughly the same. That is an uncomfortable position, and it is not your fault.

The way out is not to learn the technology. It is to ask questions where a vague answer is itself the answer. Here are twelve, with what good sounds like.

About the work itself

1. What exactly is included, and what gets billed separately? You want a plain list, not a tier name. The usual extras are project work, migrations, new starter setups, and out-of-hours calls. A good provider tells you before you ask.

2. What are your response times, and what happens if you miss them? "We aim to respond quickly" is not a commitment. Ask for hours, ask how urgency is decided, and ask what a missed target actually costs them. A target with nothing behind it is a hope.

3. Who actually picks up when I call? Find out whether you get somebody who knows your setup or a queue that starts from zero every time. This is the single biggest difference in day-to-day experience, and it rarely appears in a proposal.

4. What are your hours, and what counts as an emergency? Get the definition in writing. Yours and theirs may differ considerably at seven on a Friday evening.

About your safety

5. How do you handle backups, and when did you last test a restore? The second half is the real question. Any provider takes backups. Fewer verify them. Ask when they last restored something on purpose and what happened.

6. What security is included as standard? Multi-factor authentication, email filtering, protection on devices, and the domain records that stop somebody impersonating you. If any of that is an upgrade rather than a baseline, ask why.

7. Will you tell me when you have made a mistake? An unusual question, and a revealing one. Everyone gets something wrong eventually. The ones worth hiring say so before you notice.

About staying in control

8. Do I own my domain, my data, and my accounts? The answer must be yes, without qualification. Your domain should be registered to you, and you should hold the ultimate access to your own systems.

9. If I leave, what does that look like? Ask for the process, the timeline, and the cost. A provider confident in their work has a clean answer. A provider who has made leaving deliberately painful will get vague here, and that vagueness is the most useful thing you will learn all meeting.

10. What are you doing that I could stop paying for? Almost nobody asks this. The answers tell you whether you are talking to an adviser or a salesperson.

About them

11. Can I speak to a customer who is my size and in my situation? Not their largest client. One that looks like you. Then ask that customer the question that matters: what has gone wrong, and how did they handle it?

12. What sort of business are you not right for? A provider who claims to suit everyone has not thought about it, or is not telling you. Anyone good can describe their poor fit in one sentence.

Answers that should end the conversation

  • Anything about your own domain or data where the answer is not straightforwardly yours.
  • Pressure to sign today, or a discount that expires at the end of the meeting.
  • Jargon that survives a request for plain English. Once is a habit. Twice, after you have asked, is a choice.
  • Reluctance to put response times in writing.
  • A quote you cannot break down into what it covers.

The underlying test

You are not assessing technical skill in these meetings, and you would not be able to. You are assessing whether this is somebody who explains things straight when there is no particular advantage in doing so.

Technical competence is common. Being told the truth about what you need, including when the answer is "less than you are asking for," is not. Hire for the second one, because you can verify it in a conversation and you cannot verify the first until something has already gone wrong.

Putting this list in front of us? Good — please do. Ask Faber, or hit the chat and talk to a person, and we will answer every one of the twelve plainly. Including the ones about leaving, and including the one about what you could stop paying for.