10 Questions to Ask Before Hiring an IT Support Company
The questions that separate great partners from expensive disappointments.
1. What's your average response time — and how do you measure it?
Response time is the gap between when you report an issue and when someone starts working on it. Ask for their actual average (e.g., "under 30 minutes for critical") and whether it's tracked in a ticketing system. If they can't give a number or say "we're fast," that's a red flag. A good answer includes a defined SLA and how they report on it.
2. Do you have experience in our industry?
Healthcare, legal, and finance have compliance and security requirements that generic IT shops may not understand. Ask for 2–3 clients in your vertical and what they did for them. You don't always need a specialist, but you do need someone who knows the rules that apply to you.
3. What does your onboarding process look like?
Onboarding is when the provider learns your environment and sets up monitoring, backup, and access. A vague "we'll get you set up" is risky. Look for a defined timeline, a checklist (documentation, asset list, security baseline), and a single point of contact. Poor onboarding leads to missed issues and finger-pointing later.
4. How do you handle after-hours emergencies?
If your server goes down at 10 p.m., who answers? Is after-hours included or an add-on? Is it a real person or a callback queue? Get clarity on definition of "emergency," response commitment, and extra cost. Many providers charge a premium for after-hours or limit it to critical-only.
5. What security tools and practices do you include as standard?
At minimum you want endpoint protection, patch management, and backup. Ask if they include EDR, MFA enforcement, and security awareness training. Understand what's baseline vs. add-on and how they respond to incidents (ransomware, breach). "We take security seriously" isn't enough — get specifics.
6. How is pricing structured and what's not included?
Is it per-user, per-device, or flat fee? What's in scope (helpdesk, monitoring, backup, patching) and what's extra (onsite visits, projects, after-hours, licensing)? Ask for a sample agreement and look for auto-renewal terms and price increase caps. No surprises later.
7. Can we speak to current clients?
References matter. Ask for 1–2 clients of similar size and industry. When you talk to them, ask about response times, communication, and whether the provider delivered on what they promised. If the MSP won't provide references, consider it a warning sign.
8. What happens if we want to leave — what's the exit process?
You need to know how to get your data, credentials, and access back. Ask about notice period, transition support, and whether there are exit fees or data handover costs. A provider that makes it hard to leave is one to avoid.
9. Do you have technicians who can come onsite?
Remote support handles most issues, but hardware, cabling, and face-to-face meetings sometimes require boots on the ground. Ask how onsite visits work — included, per-trip, or not offered — and typical availability. If you have multiple locations, ask about coverage in each area.
10. How do you communicate with us day to day?
Will you have a single account manager or a ticket queue? How do you reach them — email, phone, portal? How often do you get reports or reviews? You want a clear channel and predictable touchpoints so you're not left wondering who to call or how things are going.