Every founder we talk to compares managed IT vendors on the same two axes: price and SLA response time. Those matter, but they're table stakes - they don't predict whether the relationship will still be working in year three.
The better questions are about ownership. Who actually architects the solution - a senior engineer who understands your business, or a template applied by whoever's on shift? Can you name the person accountable for your account, or is it a rotating queue of tickets? What happens when something falls outside the SOW - is it a change-order fight, or a conversation?
We'd also push on evidence, not promises: ask for a reference client in a similar industry, ask what their last migration actually cost versus the original estimate, and ask how they handle security incidents they didn't cause. A partner who's comfortable answering all three is worth a long look. One who deflects is telling you something too.
Finally, weigh how they think about your data and IP. A managed IT partner touches your most sensitive systems - identity, infrastructure, sometimes customer data. Make sure their security posture, compliance certifications, and data-handling agreements are as rigorous as you'd expect from an employee, not a vendor.
