Choosing the Right MSP: 15 Questions to Ask Before You Sign
An honest buyer’s guide from people who’d rather you make the right choice — even if it’s not us
Published by All IT Services | March 2026
Finding an IT partner shouldn’t feel like buying a used car
Switching IT providers — or choosing one for the first time — is one of those decisions that businesses put off for years. Every MSP’s website says roughly the same thing: “proactive support,” “strategic partnership,” “enterprise-grade security.” It’s hard to tell who’s genuinely good and who’s just good at marketing.
This guide gives you 15 specific questions to ask any MSP you’re evaluating — and what a good answer looks like versus a red flag.
Before you start: know what you need
Spend 30 minutes writing down: staff count and locations, core business applications, current IT pain points, budget expectations, and any compliance or regulatory requirements.
The 15 questions
1. “What does your onboarding process look like?”
Good answer: “We run a structured onboarding over two to four weeks. Full audit, documentation, tool deployment, transition coordination. No charge for onboarding.”
Red flag: “We’ll just remote in and install our tools. Should take a day or two.”
2. “What’s your average response time?”
Good answer: “Under 15 minutes for critical issues, under one hour for standard. We track resolution time too — 80% same-day target.”
Red flag: Vague answers like “we’re very responsive” without metrics.
3. “Who answers the phone when I call?”
Good answer: “A qualified technician directly. No dispatchers or call centres.”
Red flag: “Your call will be logged by our service desk team and assigned.”
4. “Do you offer after-hours and weekend support?”
Good answer: “24/7 for critical issues, included in your agreement, no additional charge.”
Red flag: “Standard hours 8-5 Monday to Friday. After-hours at additional rate.”
5. “What’s included in the monthly fee?”
Good answer: “Per-user-per-month includes unlimited remote and on-site support, monitoring, patching, endpoint security, backup management, and after-hours support. Projects and hardware quoted separately.”
Red flag: Very low base price with a long list of costly add-ons.
6. “How do you handle cybersecurity?”
Good answer: “EDR on all devices, enforced MFA, defined patching schedule, email security with DMARC, security awareness training. Aligned with the ACSC Essential Eight.”
Red flag: “We install antivirus and keep it updated.”
7. “What’s your approach to backups?”
Good answer: “Daily backups, stored locally and in an Australian cloud data centre. We test restoration quarterly and provide reports.”
Red flag: “We set up backups during onboarding and monitor for failures.” Monitoring is passive — you need proactive testing.
8. “Can you support our specific industry?”
Good answer: Names relevant regulations, platforms, and challenges. Offers a case study from a similar client.
Red flag: “We work with all industries” without specific examples.
9. “What does your strategic advisory look like?”
Good answer: “Quarterly business reviews covering environment health, projects, budget, security, and strategic recommendations. Think virtual CIO.”
Red flag: “We’re available if you have questions.”
10. “What happens if we want to leave?”
Good answer: “Month-to-month after an initial period. Full documentation handover, credential transfer, and cooperation with your new provider.”
Red flag: “36-month contract with 12-month notice period.”
11. “How do you handle projects?”
Good answer: “Scoped and quoted separately. Dedicated project manager, detailed scope of work and timeline.”
Red flag: Unclear boundaries between “support” and “project.”
12. “What monitoring and reporting do you provide?”
Good answer: “Monthly reports on ticket volumes, resolution times, system health, security events. Client portal for real-time visibility.”
Red flag: “We can pull a report if you need one.”
13. “What certifications do you hold?”
Good answer: Microsoft Partner status (Solutions Partner), relevant vendor certifications, industry certifications.
Red flag: No certifications or expired ones.
14. “Can you provide references?”
Good answer: “Here are three references from similar businesses. Contact them directly.”
Red flag: Reluctance to provide references in your sector.
15. “What makes you different?”
Good answer: A specific, evidence-backed answer reflecting actual strengths.
Red flag: Generic platitudes like “we care about our clients.”
A few final tips
Get everything in writing. Promises made during sales should be reflected in the service agreement.
Ask about their team. How many engineers? What’s turnover like? Where are they located?
Visit their office. You’re entering a relationship that could last years.
Trust your gut. If something feels off during sales, it’s not going to get better after you sign.
The bottom line
The right MSP will make your technology invisible — it just works, your team is productive, your data is secure. The wrong one will be a source of constant frustration, risk, and unexpected costs. Take your time. Ask the hard questions.
Want to see how we’d answer these questions?
We’d be happy to walk you through our answers to every one of these 15 questions — with evidence, references, and zero sales pressure.
Reach out to Tom Buckley at All IT Services. Call (02) 8073 4848 or drop Tom an email. We’ll give you a straight answer on whether we’re the right fit, and if we’re not, we’ll tell you that too.
Sources and references:
– Australian Cyber Security Centre — Essential Eight (cyber.gov.au)
– CompTIA — Managed Services industry research (comptia.org)
– Microsoft — Solutions Partner designations (partner.microsoft.com)
– Office of the Australian Information Commissioner — Privacy Act 1988 guidance (oaic.gov.au)