Use this list whether you're evaluating Simply IT or any other provider. The right answers separate operators from order-takers.
Will they sign a Business Associate Agreement?
If your business handles protected health information (medical, dental, veterinary) or operates under FTC Safeguards / ABA cybersecurity rules, your IT provider needs to sign a BAA. Many MSPs cannot — they aren't structured to take on the responsibility. If your provider has never offered one, they're not equipped to serve regulated industries.
What's their actual response time?
Ask for the documented target, not a marketing claim. Mid-market MSPs typically target 15-minute remote response and same-business-day on-site for critical issues. Anything past 4 hours during business hours is a red flag for a business that depends on technology to operate.
Is pricing published or quote-only?
Quote-only pricing isn't automatically bad — but it's the easiest place for surprise invoices to live. Look for an MSP that publishes tier rates, list per-user costs, and shows you exactly what's included before you sign anything. That same transparency carries into the monthly invoice.
What's the cancellation policy?
Multi-year contracts with steep penalties exist to lock you in. A confident MSP doesn't need a contract to keep your business — they let their service do that. 90-day notice for cancellation is reasonable; anything longer should raise a question.
Are they local — or routed through a national help desk?
When something is on fire, you want to talk to someone who's worked on your network before, not a Tier-1 tech four states away reading from a script. Local doesn't mean small; it means accountable. Ask who specifically will answer your ticket on a Wednesday afternoon.
Do they understand your industry's compliance posture?
HIPAA technical safeguards, FTC Safeguards Rule documentation, ABA Rule 1.6(c) reasonable efforts — these aren't bonus skills, they're the baseline for serving regulated practices. If their answer to "what does HIPAA require of an IT environment" is vague, they don't have the depth.
Are they actually a vendor partner — or just a reseller?
Authorized partner status (Microsoft CSP, WatchGuard, Intermedia, Pax8, etc.) means factory-direct support escalation paths and licensing pricing you can't get elsewhere. Resellers who buy at retail and mark up their margin can't match either.
If you fire them — what do you get back?
Ask before you sign: "When we leave, what's the data-handover package?" The answer should be a documented offboarding process that returns admin credentials, asset inventory, license documentation, and configuration. If they can't answer or describe a proprietary lock-in, walk away.