Everyone asks the same questions when they choose an IT provider — and gets the same rehearsed answers. Here's what to ask instead.
Every few years, a growing business reaches a point where IT stops being something that just works in the background and starts becoming a problem. Support is slow. Things keep breaking. Nobody really owns anything. And when it gets bad enough, someone — usually the CFO or COO — gets handed the job of finding a new provider.
So they do what anyone would do. They search for IT support in London, ask around for recommendations, write a list of questions, send it to three or four suppliers, and wait for the answers to come back.
Here's the thing: the answers are always the same.
Response times? Fast. Engineers? Senior and experienced. Escalation? Clear and structured. Proactivity? Absolutely. Process? Robust and well-documented.
Every IT provider in the country will tell you what you want to hear, because the questions you're asking are the questions everyone asks — and every supplier has learned exactly how to answer them. Some are even letting AI write the responses now, which makes the problem worse. You get polished, confident, completely indistinguishable answers to questions that were never going to separate good providers from average ones in the first place.
The businesses asking those questions are doing the sensible thing. They're measuring for the pain they're in. A slow, unresponsive provider makes you ask about response times. A junior helpdesk that can't resolve anything makes you ask about escalation. A reactive provider that never flags problems early makes you ask about proactivity. The questions feel right because they map directly onto real problems.
They're still the wrong questions — because anyone can claim to fix them.
What you're really trying to find out
When a business asks about SLA response times, what it actually wants to know is: will someone pick up when something goes wrong, and will it get fixed quickly?
When it asks about named engineers, what it actually wants to know is: will someone understand our business, remember our history, and not make us explain ourselves from scratch every time?
When it asks about escalation paths, what it actually wants to know is: when something is genuinely serious, will the right people deal with it — and will anyone take ownership?
These are legitimate things to want. They're just not things you can verify by asking for them on a form.
The questions worth asking
What do your existing clients say — and can we talk to them?
This is the single most useful thing you can do. Not a written testimonial. Not a case study. An actual conversation, without the MSP present, with someone running a similar business.
Ask them what happens when something goes wrong. How long they've been with the provider, and why they haven't left. Whether anything has surprised them — good or bad. Whether they'd recommend the provider without hesitation.
A provider that is genuinely confident in its service will arrange these introductions immediately and without conditions. One that is hesitant, that wants to manage the process, or that offers written references instead — that tells you something. It's worth looking at what our clients say before you even start the conversation.
What does your team actually look like?
Not "how many engineers do you have." Specifically: who will be handling our tickets day to day? What's their background? How long have they been with you?
High staff turnover in an MSP is a serious red flag. So is a model that relies on apprentices or first-line handlers who log tickets and pass them on. You want experienced people who can diagnose and resolve on first contact. Ask directly. Push for specifics.
How do you handle recurring problems?
Any decent MSP resolves tickets. The question is what happens next. If the same issue comes back three times, what does that trigger? Who reviews it? What gets changed?
Proactivity isn't a personality trait — it's a process. If a provider can't describe it clearly, with a real example, it probably doesn't have one.
Which of your last few clients left, and why?
This will catch most people off guard, which is exactly why it's useful. A good answer sounds something like: "One was acquired and IT moved in-house. Another outgrew us and built an internal team. We've had a handful of clients for over ten years."
A bad answer is vague, defensive, or focuses on things outside the provider's control. You're not looking for a perfect record — you're looking for self-awareness and honesty.
What will the first 90 days actually look like?
Onboarding is where most MSPs let businesses down. Ask for specifics. Who runs it? What gets documented, and when? How is the handover from the previous provider managed? What does good look like at the end of it?
If the answer is generic, the onboarding probably will be too.
The thing no SLA can tell you
Response time targets are easy to write and easy to miss. What they can't capture is what it actually feels like to be a client — whether your calls get answered by someone who knows what they're doing, whether problems get solved or just closed, whether the people supporting your business feel like an extension of your team or a distant service desk.
That feeling comes from culture, not process. And culture only shows up in two places: in how a team behaves when things go wrong, and in what its clients say about it when it's not in the room.
The businesses that choose IT partners well aren't the ones that send the most thorough questionnaire. They're the ones that pick up the phone and talk to people who've already made the decision.
Before you send another questionnaire
If you'd rather assess your current setup before you start shortlisting providers, our free IT Provider Scorecard walks you through the questions that matter in about five minutes — and gives you a clear, honest read on where you stand.
Ratcliff IT supports growing businesses as their IT, cybersecurity and AI partner — senior expertise, clear accountability, and a team genuinely integrated into how you work. If you're assessing your options, we'll do the one thing the rest of this article recommends: put you in touch with our existing clients first, before you commit to anything.
Call our team on 020 3551 6262 or book a no-strings discovery call at our discovery call booking page.
