Choosing a Managed IT Partner: Eleven Questions Worth Asking

The proposals all look the same

Managed service proposals converge on the same language: proactive, enterprise-grade, 24/7, single point of contact. The differences that matter are operational, and they only surface when you ask specific questions.

Questions that separate providers

• What is your median first-response time, measured over the last quarter?
• Who answers at 2am — your staff, or an overseas answering service?
• Is security monitoring included, or an upsell after the first incident?
• How often do you test client backup restores, and can I see the last report?
• What happens to my documentation and credentials if we part ways?
• Which vendors do you resell, and how does that affect your recommendations?
• Can I speak to a client of similar size in my industry?
• How do you handle onboarding and offboarding staff, and how fast?
• What is explicitly out of scope in the agreement?
• Who is my named account manager, and how often do we meet?
• How do you report on risk to a non-technical leadership team?

Fit matters more than feature lists

A twenty-person firm does not need the same operating model as a five-hundred-person one. The right partner is the one whose process matches how your business actually runs, and who will tell you plainly when something is not worth doing.