You’re not buying IT support. You’re deciding who to trust.
When you hire a managed IT provider, you hand over the keys. Literally: admin passwords, your email, your files, your firewall, and the laptops your team uses every day.
Most businesses make that decision based on a sales call and a price sheet. Then, six months in, they discover what “unlimited support” actually meant. Or that nobody answers after 5pm. Or that they can’t get their own passwords back.
Those surprises are avoidable. They usually come down to questions nobody asked before signing.
So here are the questions we’d ask if we were in your seat. Ask them of every provider you’re considering, including us. A good partner will answer each one clearly, in writing, without getting uncomfortable. At the end, we’ll show you exactly how Red Key answers them.
The 7 questions
1. What’s included in the monthly fee, and what isn’t?
“Unlimited support” means nothing until you see the list. Ask for two lists: what the flat fee covers, and what gets billed separately (new laptop setups, office moves, projects, licenses).
Good answer: both lists, in writing, before you sign. Red flag: “Don’t worry, it’s all covered.”
2. What happens when something breaks at 7pm on a Friday?
Outages don’t keep business hours. Ask what the standard support hours are, how emergencies are handled outside them, and how you escalate.
Good answer: specific hours, a clear emergency process, and an upfront rate for non-emergency after-hours work. Red flag: “Just call us anytime” with no process behind it.
3. How do you know you’re doing a good job, and will you show me?
Every provider says their support is great. Ask how they measure it, and whether you’ll see the numbers.
Good answer: a real metric like ticket satisfaction scores, plus regular reporting on your environment. Red flag: testimonials only.
4. Who owns our data, passwords, and admin accounts?
This is the question that matters most if the relationship ever ends. You should never be locked out of your own business.
Good answer: “You do,” stated in the contract, with documented access to your own passwords and systems. Red flag: vagueness, or credentials living only in one technician’s head.
5. What’s the plan beyond fixing tickets?
Fixing what breaks is the minimum. A partner should help you decide what to replace, what to budget for, and what’s coming next.
Good answer: scheduled strategy meetings, an assessment of where you stand today, and a written multi-year roadmap. Red flag: you only hear from them when something’s broken.
6. What do you need from us?
IT works best as a partnership, and good providers are upfront about what they need from you. That might be notice before a new hire starts, or keeping equipment within supported standards.
Good answer: a short, clear list of expectations. Red flag: no list, followed later by “that’s not covered because you didn’t tell us.”
7. How does the contract work, including how we’d leave?
Ask about term length, renewal, notice periods, and what offboarding looks like. Nobody plans to leave, but you should know the path.
Also ask which documents govern the relationship. Many providers have general terms anyone can read, plus a service agreement specific to your account.
Good answer: general terms you can read anytime, a service agreement you can review before signing if you ask, and a defined offboarding process. Red flag: a provider who won’t show you the terms when you ask, or can’t clearly explain renewal and exit.
How Red Key answers
We said we’d answer our own questions. Here they are, as plainly as we can put them.
| Question | Red Key’s answer |
|---|---|
| What’s included? | The managed fee covers guidance from a Technology Strategy Director, remote and onsite helpdesk, network and security monitoring, patching, new hire setup and offboarding, and procurement management. Billed separately: hardware and licenses, new device setups, projects, and moves. You get both lists before you sign. |
| After-hours? | Standard support runs Mon–Fri, 8:30am–5pm. On-call engineers cover emergencies on weekday mornings and evenings and on weekends; typing “911” in a support email escalates it. Non-emergency after-hours work is billed at 1.5x our standard rate, and only with your approval. |
| How do you measure it? | Our average ticket satisfaction is 99.4%, and every bad rating gets reviewed. You also get a monthly technology report and a live view of your tickets, assets, and IT health in the Red Key app. |
| Who owns our data? | You do, and our agreement says so. Your passwords, processes, and documentation live in a portal you can access anytime. |
| What’s the plan? | Your Technology Strategy Director leads regular Technology Strategy Meetings. It starts with a 130+ point IT health assessment that becomes a practical 3-year roadmap, with a budget forecast you can see. |
| What do you need from us? | One point of contact, 3 business days’ notice before a new hire starts, same-day notice when someone leaves, and equipment that meets our published standards at redkeysolutions.com/standards. |
| How does the contract work? | Agreements run 12 months and renew annually, with 60 days’ written notice to cancel. Our general Master Services Agreement is published at redkeysolutions.com/msa, so you can read it anytime, even before we talk. Your account-specific Managed IT agreement arrives with e-signature, and if you’d like to review it earlier, just ask and we’ll send it. If you leave, there’s a defined offboarding process to hand everything back. |
Ask every provider. Compare the answers.
Since 2002, we’ve learned that the best IT relationships aren’t built on promises. They’re built on clear expectations, set early and kept.
So take these questions into every conversation you have, ours included. The providers worth trusting will be glad you asked.
If you’d like to hear our answers in person, request a proposal or schedule a consultation with us.