What Questions To Ask Your IT Support Provider

What Questions Should I Ask My IT Support Provider?

I was at a Kent business breakfast meeting a few weeks back – usual scene, lukewarm bacon, somebody hijacking the room banging on about LinkedIn – when a chap I’d never met grabbed me by the elbow.

“Jacqui,” he said, “my IT contract’s up at Christmas. I’ve got three quotes lined up. What on earth do I actually ask them?”

He’d already been on Google, of course. He had a list. It was the same list everybody has. “What’s your uptime guarantee?” “What does your SLA stand at?” “Tell me about your service catalogue.” All very tidy on paper. All fairly useless in practice – and what do half the acronyms mean anyway?

So I told him what I’d ask if I were sat where he was. And then I thought – if he’s asking, plenty of others must be. So here’s the proper list. The questions that’ll actually tell you whether the firm in front of you is any good, or whether you’re about to sign up to multiple years of pain?

That’s my first question.

How long is the contract and how do I get out of it?

I’ve sat in many meetings where providers tie clients into long contracts, with limited “get out” ability – brief windows of opportunity you don’t even know about, months of notice required, and a complete change of attitude the moment you try to use them. If the contract is onerous, long, or laced with complex exit clauses, that’s an alarm bell for me. The same can be said for printer contracts, phone contracts, and any other service to be honest.

Who picks up the phone when I ring?

This second one tells you almost everything.

Some firms have a real person on the end of the line at 8.30am on a Monday. Others have a portal you log into, where you fill in a form, and somebody somewhere gets back to you in due course. Both can technically work. Only one of them will help you when somebody’s printer is jammed five minutes before a board meeting. And even then – is the person picking up a trained engineer, or a receptionist? There’s a huge difference in the level of help you’ll actually get.

If they say “we have a ticketing system,” fine. Ask the follow-up: and what happens between me logging the ticket and somebody actually picking it up? If they fudge that, you have your answer.

How fast will you actually be there?

Not “what’s your SLA.” That’s the wrong question, because every contract has a number on it and most of those numbers are nonsense – honestly, an SLA doesn’t cut the mustard when you need your internet back, or your Wi-Fi to work. I see plenty of businesses thoroughly fed up with large providers based up the country, reluctant to visit site, charging a fortune for engineer visits and hotel fees on the rare occasions they do finally leave their offices.

Ask: if my server goes down at 10am on a Tuesday, what time will an engineer have eyes on the problem? Then ask the same question for 5pm on a Friday. The honest providers will give you a different answer for each. The ones who say “four hours, every time” either don’t mean it, or they’re not telling you what “four hours” actually buys you.

What’s not included?

The single best question, in my view. Better than any of the others.

Every IT support contract has stuff that isn’t covered. Project work. New hardware. Out-of-hours callouts. Email migrations. The list runs on a bit once you start looking. If a provider tells you “everything’s included” they’ve either not read their own contract, or they’re hoping you won’t.

Ask straight out: what’s outside the contract, and how do you charge for it? A good answer is specific and short. A bad answer is “oh, well, it depends.” Run a mile from “it depends.”

Can I talk to a client of yours?

Not a logo on a website. Not a glossy case study. An actual customer. A real business owner you can ring up.

Any provider worth their salt has half a dozen clients who’ll happily spend twenty minutes telling you the truth – good and bad. If they won’t connect you with anyone, that’s not because they’re protecting privacy. It’s because nobody wants to take the call.

Where’s my data, and what happens to it if I leave?

Two questions in one, and they go together.

First: where is my data backed up, how often, and have you actually tested a restore recently? You want a clear answer. Daily. Off-site. Encrypted. Tested last month. Not “we use a backup product.” Anyone can buy a backup product. The question is whether they’ve ever pressed the restore button under pressure.

Second, and more important: if I decide to leave you in 18 months, what happens to my data and how do you give it back to me? A good provider has a clear answer because they’ve done it before. A bad one gets a bit awkward and starts talking about “exit fees.” That’s your tell.

Are you patching, or just reacting?

This is the one most small business owners don’t know to ask, and it matters more than almost anything else.

Reactive support means they fix things when they break. Proactive support means they’re updating, monitoring and patching your kit so things break less often in the first place. The price difference is meaningful. The outcome difference is enormous.

Ask: what proactive work do you do on my systems every month, and how will I know it’s been done? If they can’t tell you what they’ll do, or how they’ll prove it, they’re not really doing it.

Have you got the certifications that actually mean something?

There are about a hundred IT certifications and most of them are wallpaper. The ones that aren’t:

  • ISO 27001 – the international standard for information security. Hard to get, harder to keep. If they’ve got it, they take security seriously.
  • Cyber Essentials Plus – proper UK government-backed scheme, with an actual technical audit rather than a tick-box form.

I’d expect any decent provider to hold at least one of those two.

  • ISO 9001 – quality management. Tells you they have process discipline, not just enthusiasm.

Ask which certifications you hold and when they were last audited. Anyone can claim to be “ISO accredited.” Far fewer have actually paid the auditors recently.

Do you actually understand my kind of business?

Last one, and the easiest to forget.

If you’re a 30-person firm of solicitors in Maidstone, you don’t really want an MSP whose other clients are all 500-seat manufacturers in Birmingham. The technology might overlap. The way you work, the rules you operate under, the speed at which things have to happen – none of that overlaps.

Ask: how many businesses like mine do you currently look after, and what’s specifically different about how you support them? If they can’t tell you, they probably don’t know.

One last thing – go on your gut

After all the questions are answered, there’s one more thing to do. Sit with it for a day.

Did the person you spoke to feel like somebody you could ring at half past four on a Friday with a nasty problem and a knot in your stomach?

If the answer is yes, the rest will probably be alright. If it’s no, no amount of certification or response-time guarantees will save you.

If you’d like to put any of these questions to me directly, give me a call on 01227 371375. I’ll answer them honestly – including the awkward ones. And if I’m not the right fit for your business, I’ll tell you that too. There’s no point in either of us pretending.

Jacqui Offen IT Director, JJ Systems UK Ltd

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