IT Provider Evaluation Guide
Not sure whether your IT is being managed the way it should be?
Use 28 practical questions to evaluate your IT support, cybersecurity, recovery planning and technology strategy—before deciding what actually needs to change.
No sales pitch. No arbitrary score. Just practical questions to help you understand what deserves a closer look.
11 pages · Fillable and printable · Version 1.4
01 / Start with the right question
A bad IT experience doesn’t always mean you need a new IT provider.
A frustrating incident is a reason to ask questions. It isn’t automatically a verdict on the people managing your IT.
Technology
Is the technology itself creating the problem?
Support Process
Is the support process getting in the way?
Responsibility
Is responsibility unclear between teams or vendors?
Communication
Are expectations or recommendations not being communicated?
Strategy
Is the same underlying problem returning without a plan?
This guide helps you look beyond the incident. The next step might be a clearer conversation, a better process, a technology decision—or a closer look at whether the relationship is meeting your business’s needs.
02 / What’s inside
Seven areas.
Twenty-eight useful questions.
Evaluate the way IT is managed, not how much technical terminology you know. Each category focuses on what leadership should be able to understand and expect.
01
Accountability
Who owns what—and who coordinates an issue through resolution?
02
Support
Can employees get help directly, while leadership retains useful visibility?
03
Proactive Management
Are systems maintained and potential problems identified before disruption?
04
Recovery
Do you know how much downtime and data loss the business can tolerate?
05
Cybersecurity
Are risks actively managed—and can employees report mistakes immediately?
06
Planning & Budgeting
Are future investments connected to business needs and operating experience?
07
Communication
Do you understand what IT is doing, why it matters and what needs a decision?
Yes · Where you have confidence
No · Where you see a gap
Not Sure · Where you need visibility
28 questions. Yes / No / Not Sure. No manufactured “IT health score.” Use your answers to identify the conversations worth having.
03 / Visibility without the help desk role
Your support tickets should tell you more than what’s broken.
Employees should be able to contact IT directly for routine problems. Management should not have to approve, relay, monitor and follow up on every request.
01
Employee issue
01
Direct IT support
01
Ticket history
01
Patterns & root causes
01
Executive review
01
Priorities & IT strategy
IT turns activity into understanding.
Consistently recorded support activity is business data. IT should analyze recurring issues, explain the underlying problem and its business impact, and recommend the next step.
Leadership focuses on leadership decisions.
Regular executive reviews should connect that information to priorities, risk, budgets and longer-term plans—not hand management a pile of incidents to diagnose.
Good IT management connects what happens today with what the business should plan for tomorrow.
04 / Inside the guide
Know what questions to ask—even if you don’t know IT.
Can employees get routine help without management becoming the help desk? How much downtime and data loss can the business tolerate? The guide turns those concerns into questions you can discuss.
Support · Visibility without managing every ticket
Recovery · Start with downtime and data loss
Your priorities · Choose the questions that matter most
Work through it. Keep what matters.
Make your Yes / No / Not Sure selections, record the 3–5 questions you want to discuss and save your completed PDF. Prefer paper? Print the guide and complete the same exercise by hand.
Select any page to enlarge it. These are actual pages from the finished Version 1.4 guide.
05 / A clearer conversation starts here
Get the IT Provider Evaluation Guide
Work through the questions at your own pace, then discuss what you learned with whoever manages your IT.
- 28 executive-level questions across seven categories
- Yes / No / Not Sure—without a score
- Guidance on what good answers look like
- Five spaces to identify your discussion priorities
- 11 pages to fill in digitally or complete on paper
06 / After you’ve read it
What if the guide raises questions?
- Education
- Self-Evaluation
- Current-Provider Conversation
- Outside Assessment When Warranted
Can employees get routine help without management becoming the help desk? How much downtime and data loss can the business tolerate? The guide turns those concerns into questions you can discuss.
If those discussions suggest an outside perspective would help, a Free Network Assessment can provide an initial executive-level view. It is not a formal compliance or insurance audit.
Have a specific IT problem or question?