15 Questions to Ask Before Signing Your Next IT Support Contract

I sell IT support for a living, so take this with whatever pinch of salt you like. But I’ve also sat on the buyer’s side of the table often enough to know that most hospitality operators sign the wrong contract because they ask the wrong questions - or worse, they ask the right questions and accept fuzzy answers because the salesperson is charming and the slide deck is tidy.

Here are 15 questions I’d ask any MSP - including us - before handing over your estate. Each one has a version of what a good answer actually sounds like. If the provider can’t give you a clean response to all 15, you’ve got your decision.

1. What percentage of your revenue comes from hospitality customers?

This is the first question and it should be the first filter. A generalist MSP doing 5% hospitality is going to treat your payment terminal outage on a Saturday night the same way they treat a solicitor’s broken printer on a Tuesday morning. That’s not a dig at solicitors - it’s just a completely different operational rhythm.

A good answer sounds like: “Somewhere between 60 and 100%, and here are the types of venues we support - casual dining groups, pub co’s, hotel groups, QSR.” If they hesitate, or if the number is under about 30%, you’re a diversification bet for them, not a core customer. Read more about why this matters on our hospitality IT support page.

2. What’s your SLA for a “payment terminal down” ticket at 8pm Saturday?

Every MSP has an SLA document. Almost none of them have an SLA document that distinguishes between “printer jammed” and “we cannot take card payments during peak service”. If those two tickets are in the same bucket, the bucket is wrong.

A good answer sounds like: “P1, 15 minute response, engineer on the phone inside 15, remote fix attempt inside 30, onsite dispatch if remote fails, and here’s the out-of-hours rota that makes that possible.” If they start mumbling about “best efforts after 6pm”, end the meeting.

3. Who covers our account if our primary engineer leaves the firm?

MSPs lose engineers. That’s just the industry. The question is what happens to your knowledge when it walks out the door. If the only person who knows your estate is one named engineer, you’ve bought a single point of failure and paid a monthly fee for the privilege.

A good answer sounds like: “You’ll have a named primary and a named secondary, both of whom have been into your sites. Our documentation is centralised in a platform the whole service desk can access, and we do shadow rotations so knowledge isn’t trapped in one head.” If the answer is “don’t worry, Dave’s been with us ages”, worry.

4. What’s your engineer tenure - average and median?

Tenure is one of the few numbers that’s actually hard to fake. A service desk with an average tenure of 18 months is a service desk that’s constantly retraining, and retraining on your estate. You don’t want to be the training ground.

A good answer sounds like a specific number - “our service desk median tenure is three years and four months” - followed by an explanation of why. Career paths, salary bands, working patterns. If they can’t quote the number, they haven’t looked, which tells you something on its own.

5. How do you charge for out-of-hours work, if at all?

Hospitality doesn’t stop at 5pm. Neither should your support contract. But plenty of MSPs will quote a headline price that looks brilliant and then charge you £180 an hour, minimum two hours, every time something breaks on a Saturday night. Do that twelve times in a year and your cheap contract isn’t cheap any more.

A good answer sounds like: “Out-of-hours is included for P1 and P2 incidents across your core trading hours, and here’s the definition of core trading hours in the contract.” Compare it against our transparent pricing page to see what a flat, hospitality-aware contract actually looks like.

6. Do you subcontract any service desk work, and if so, where?

Some MSPs run a 24/7 service desk out of a bedroom in Manila and don’t mention it in the sales meeting. That’s fine, as long as you know. It’s not fine if you find out at 9pm on a Friday when someone who doesn’t know what a Zonal till looks like is trying to talk your duty manager through a reboot.

A good answer sounds like: “We don’t subcontract,” or “we do, here’s who, here’s where, here’s what they cover, and here’s how we train them on hospitality systems.” Either of those is workable. Evasiveness is not.

7. What monitoring and alerting will you put on our estate from day one?

“Reactive” support is a euphemism for “we’ll pick up the phone when you ring us”. That’s 2010 thinking. If your MSP isn’t monitoring your EPOS workstations, your network edge, your payment terminals and your back-of-house infrastructure proactively, they’re going to find out about most incidents from you - which means so will your customers.

A good answer sounds like a list. RMM on every endpoint. Network monitoring with alerting on circuit drops. Uptime checks on critical SaaS. A dashboard you can see. And - ideally - thresholds that have been tuned for hospitality hours, so you’re not getting paged about a till being offline when the site is closed.

8. How do you onboard a new customer - what does week one look like?

Onboarding is where the relationship is actually made or broken. A sloppy onboarding means six months of firefighting because nobody documented the quirks of your estate. A proper onboarding means that by the time the first incident lands, the engineer already knows which cupboard the switch lives in.

A good answer sounds like a phased plan. Discovery and audit in week one. Documentation and tooling deployment in weeks two and three. Shadow period with the outgoing provider if possible. Named go-live date. If they say “we’ll just take the handover email and crack on”, you’re in trouble.

9. Who handles new site openings and how do you charge for them?

If you’re growing, this matters more than almost anything else. A new site opening is a project, not a ticket, and the MSPs who do it well have a dedicated projects team with a repeatable playbook. The ones who do it badly will pull an engineer off your service desk and charge you day rate for the privilege.

A good answer sounds like: “We have a projects team separate from the service desk. Here’s our standard new-site package, here’s the price, here’s the lead time, and here’s a reference from a customer who opened three sites with us last year.”

10. What happens if we have a major incident and you’re already stretched?

Every MSP will tell you they can cope with a major incident. Fewer will tell you what happens when the major incident hits at the same time as two other major incidents at other customers. That’s the real question.

A good answer sounds like: “We have a documented major incident process, a duty manager rota, and we pull engineers off project work to backfill when P1 volumes spike. We also have a cap on customers per engineer so we don’t get into that situation in the first place.” If the answer is a shrug, the answer is a shrug.

11. Are you independent or owned by a private equity group?

Not a gotcha. Some PE-owned MSPs are excellent. But ownership affects incentives, and incentives affect service. A firm that’s being prepped for sale in 18 months is going to be under cost pressure that a founder-owned business isn’t. Ask the question so you know what you’re buying.

A good answer is simply the truth, followed by what it means for you. “We’re founder-owned and have been for twelve years” is a fine answer. “We’re PE-backed, here’s the parent, here’s our investment roadmap” is also a fine answer. “Er, it’s complicated” is not.

12. What specific hospitality tools do you support in-house (EPOS, PMS, KDS)?

“In-house” is the key phrase. Plenty of MSPs will happily log you a ticket with your EPOS vendor and bill you for the call. That’s not support - that’s a very expensive switchboard. You want a provider who can fix the till, not one who can phone the till company.

A good answer sounds like a specific list. Oracle Symphony. Zonal Aztec. Tevalis. Lightspeed. Mews. Opera. Plus the integrations between them. Plus the printer and KDS layer underneath. If they can’t name the products you actually run, they can’t support them.

13. How long is the contract? Rolling or fixed term? What’s the exit clause?

The length of contract an MSP asks for is usually inversely proportional to their confidence in their own service. Three-year lock-ins with 12-month notice periods are a red flag. So is any exit clause that requires you to give notice on a very specific date or pay the rest of the term.

A good answer sounds like: “12 months initial, then rolling monthly with 90 days’ notice, and we’ll help you offboard professionally.” Anything more restrictive is them protecting themselves from the consequences of mediocre service.

14. What’s your price escalation clause - year-on-year?

Year one is always competitive. Year two is where you find out what you actually signed. Some contracts have uncapped CPI-linked increases, which in an inflationary year means a nasty surprise. Others have a flat cap, which is cleaner.

A good answer sounds like: “CPI capped at 5%, or a fixed 3% - your choice, written into the contract.” Anything uncapped, you negotiate down or walk. The same goes for hidden “change control” fees that let them repricing half the contract the moment you add a new device.

15. What do your three most similar customers to us say about you?

This is the one most buyers skip because it feels awkward. Don’t skip it. Ask for three references from customers who look like you - similar size, similar number of sites, similar systems, similar growth trajectory. Then actually ring them. Ask them what goes wrong, not what goes right.

A good answer is three names and phone numbers inside 48 hours. A bad answer is “we’ll need to check with them first” followed by silence. Good MSPs have customers who are happy to take the call because they’ve been asked before. Also worth asking about cyber security posture while you’re at it - references are a great way to find out whether an MSP’s security story holds up in practice.

The bottom line

None of these questions are clever. None of them are designed to trip anyone up. They’re just the questions a serious buyer asks a serious supplier. If the provider in front of you can’t answer all 15 clearly, confidently and specifically, they’re not ready to sign you up - and you shouldn’t be ready to sign them up either.

If you want to run these 15 questions past us, we’ll answer every single one on a call. Book a conversation with our hospitality team and bring the list.