31 Questions to ask a current or prospective IT Services Company

Managed IT Services at a COUPLE of GURUS

One of the main benefits of hiring an outsourced IT services company (often called an IT Managed Services Provider, or MSP) is that the good ones can replace an organization’s internal IT department, at a much lower cost. So they need to develop the same level of familiarity with the infrastructure and processes, and deliver the same level of responsiveness, as an internal team.

If you are considering hiring an outsourced IT company, you need to determine if you’ll work well together, and you need to know you can trust them to become a part of your business. If you’re already working with a managed IT service company, you should make a habit of reviewing their performance on a regular basis. Are they really partnering with you to scale your business? Are you getting the return on investment that you need?

In this article, we will look at these and other questions to ask either a prospective or current managed it service provider.

What should I ask a prospective managed IT services provider?

You need to dig into how a potential IT MSP will improve your current ways of working. What do they have to offer your business that your own team is unable to provide? How are their services worth the investment you’ll be making? How will they solve the problems you have?

Here are some questions that will help you determine what they can deliver and if they’re a good fit for your business.

Depending on your business, you may want to ask the following questions:


  • How will your IT managed services give us a competitive edge?
  • Will you help with technology planning for our business?
  • How can you scale with us as our company grows?
  • How do you handle workflows and automation?
  • How will your IT managed services help us utilize the cloud and become more digitally savvy?
  • How will you enable better collaboration and innovation within our organization?
  • How can you help us work remotely?
  • Do you really take a proactive approach, or rely more on IT break/fix responses?
  • What role do expert engineers play in service delivery?
  • If we have a problem, how quickly can we expect to hear back from someone on your team?
  • Will you get to know our business and systems, to provide effective help when we call?
  • Will you meet with us regularly to check-in, or just rely on reporting?
  • What’s your reporting mechanism? How will we be able to view it?
  • Do you document your processes?
  • Are you insured?
  • What is your IT security posture?
  • Do you provide backup and disaster recovery? What happens if we experience a data breach?
  • What pricing models do you provide? How transparent is billing?
  • What does the onboarding process look like? How long will it take?
  • What references can you provide? Who in your customer community can I talk to?

How do I get the most out of my current IT managed service provider?

Once you hire an outsourced IT managed service provider, don’t forget to assess their services. Even if you feel they are delivering excellent results, you should review periodically to make sure you’re still aligned on the same goals. Are there any promises from the original agreement that have not been kept? Do they really know your business and provide effective help? Or do they take forever to fix issues? Have your IT problems actually gone down? Or does it seem like you are still struggling with IT issues?

You may find that evaluating their IT services illuminates gaps in your business IT that need addressing. Maybe you’ve outgrown your current plan, or maybe there’s more to be done to accommodate your growth.

Reassure your outsourced IT services company when reviewing your current services. You don’t want to scare them, but you do want to ensure you’re both still happy with your current agreement. If they’re doing their jobs well, a reassessment will highlight their performance, and could reveal new services you need from them—especially if your company has been growing since you first hired them.

Depending on your business, you may want to ask the following questions:

  • Can we review our current agreement? We’d like to make sure our goals are still aligned.
  • What are your current security procedures? Have they changed since we hired you?
  • When was the last time our security procedures were updated?
  • How can your team help us transition to working remotely?
  • What kind of technology planning are you offering us? How are you helping us adapt as new technologies emerge?
  • Can you share an example of how we are staying up to date with current technology?
  • How have your IT services made us more efficient over the past 6 months?
  • How have you adapted your services to meet the needs of our growing team?
  • What new IT services do you offer that we might not know about?
  • If we needed to cut back our services with you, what would you recommend?
  • If we wanted to expand our services with you, what would you recommend?

Your company IT plays a critical role in keeping your business healthy and running smoothly. When you put your company’s safety and stability in the hands of someone else, you need to know you can trust them and count on them to deliver the services you need. Don’t shy away from asking the tough questions when you’re searching for a great outsourced IT service provider for your business, and remember to check up on your current IT provider to ensure all continues to run at maximum efficiency.

Ask a COUPLE of GURUS your IT Managed Service Provider questions

a COUPLE of GURUS is an IT Managed Service Provider offering managed IT services that proactively care for your technology needs. We’d love the opportunity to show you how managed IT services and IT support are supposed to be done.

We have over 18 years of experience helping businesses like yours with IT projects, cybersecurity, regulatory compliance (such as HIPAA, PCI, CMMC), cloud services, and managed IT services.

Contact a COUPLE of GURUS to learn more about our IT services and any IT needs you may be overlooking. Or schedule your Technology Roadmap Assessment today!