Practical questions to ask any MSP across security, support, onboarding, tooling, and exit strategy — so you compare providers on substance, not sales.
A polished proposal tells only part of the story. This guide provides a structured list of practical questions you can use when evaluating managed service providers, grouped by security, support, onboarding, tooling, and exit strategy - so you can compare options on substance, not just sales polish. How to Use This Question List You don't need to ask every question in a single meeting. Instead, use this guide to structure your evaluation across two or three conversations. For each question, note not just the answer, but how clearly the provider explains it and how comfortable you feel with their approach. Share key questions in advance so providers can prepare thoughtful responses. Invite both technical and non-technical stakeholders to the conversation. Pair this guide with our articles on selecting an MSP and MSP pricing models. Security & Compliance Security is foundational. These questions help you understand the provider's security posture and how it aligns with your business requirements. A provider's answers here will tell you whether they treat security as a core discipline or an afterthought, and whether their approach will scale alongside your business. Q1: Which security tools do you standardize on for endpoints, email, and identity? Why it matters: You want a coherent, well-understood security stack rather than a random mix of tools. Standardization improves response times and reduces blind spots. When every client runs the same toolset, the provider's engineers develop deep expertise with those products and can troubleshoot faster. Good answer: A clear explanation of their EDR, email security, MFA, and backup tools, why they chose them, and how they monitor alerts 24/7. Q2: How do you monitor for and respond to security incidents? Why it matters: Detection and response processes determine how quickly an attacker is contained and how much data or time you lose. The