Twelve questions to ask a managed service provider before you sign
Most MSP proposals look identical on paper. These are the questions that separate them — including the ones we would rather you did not ask us.
Managed service proposals converge. Everyone has a 24×7 desk, everyone is a Microsoft partner, everyone has a portal, and everyone’s response targets look reassuringly similar in a table.
The differences are real, but they do not show up in the marketing. These are the questions that surface them. Ask them of us too.
On the service desk
1. Who actually answers at 2am, and where are they? “24×7” can mean an Australian engineer on call, an offshore desk, or an answering service that raises a ticket for the morning. All three are legitimate business models. Only one of them is what most buyers assume they are getting. Ask for the arrangement in writing.
2. What is the escalation path, by name? Not “escalates to L3” — who, specifically, and how long does it take to reach them. If nobody can answer this, the escalation path is theoretical.
3. Does the person who built our environment still work on it? Transition teams and run teams are often entirely different populations. That is not automatically bad, but the handover is where knowledge goes to die. Ask how it is transferred and what is documented.
On the commercials
4. What is out of scope? The inclusions list is marketing. The exclusions list is the contract. Ask for it specifically, and read what happens when something falls outside it — hourly rate, response target, approval process.
5. What happens at renewal if we want to leave? Ask about exit assistance: who owns the documentation, who owns the tooling and admin credentials, and what it costs to have your environment handed to somebody else. A provider that has thought about this is a provider confident you will not need it.
6. Are we buying capacity or outcomes? A block of hours and a managed service are different products at similar prices. If the agreement is capacity-based, work under-consumed is work the provider has no incentive to do proactively.
On the technical position
7. Show me a real monthly report — redacted, from an actual customer. Sample reports are designed. Real reports show what the provider chose to measure, whether they report their own misses, and whether anybody would act on them.
8. What did you get wrong last year, and what changed? The best answer to this question is specific and slightly uncomfortable. A provider with no failures either has no customers or is not telling you.
9. Which platforms do you recommend against, and why? A provider that recommends everything they sell and nothing they do not is a reseller with a service wrapper. You want a position, and reasons.
On security and compliance
10. What certifications do you hold, as a company, versus what your solutions hold? This distinction is routinely blurred in Australian government sales, and it matters. A vendor product may be IRAP-assessed at PROTECTED while the partner delivering it holds no assessment of its own. Both facts can be true; conflating them is what you are watching for. Ask them to state, precisely, what is assessed and what is not.
11. Who touches our environment, where are they, and what vetting do they have? Onshore or offshore, employees or subcontractors, and whether security-cleared personnel are actually available or merely mentioned. If your security plan has personnel requirements, get the answer before the contract, not during the first incident.
12. When did you last restore something? Not “do you take backups” — when did a restore last happen, of what, how long did it take, and is there a report. This single question separates operators from vendors more reliably than anything else on this list.
Two more, if you have the appetite
Can I speak to a customer who left you? Nobody enjoys this question. The answer tells you more than three reference calls with happy customers.
What would you fix first in our environment, before we have paid you anything? A provider who cannot give you a useful answer after a first conversation has not been listening, and a provider who gives you six answers is guessing. One specific, well-reasoned answer is the signal.
We publish this because we would rather be chosen by somebody who asked. If you want to put these to us, start here — or read how we structure an engagement first.