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Kharmela Mindanao

By: Kharmela Mindanao on October 1st, 2021

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20 Questions to Ask When Choosing the Best Managed IT (MSP) in 2022

Managed IT Services

Learn how to choose the best Managed IT services for your company. Read about the types of questions you need to ask before dealing with an MSP. 


Editor's note: This post was originally published on November 17, 2020, and has been revised for clarity and comprehensiveness.

In the current environment where technology is essential to the growth of a business, you need to know you’re putting your IT infrastructure in the hands of someone you can trust.  

As an MSP, Intelligent Technical Solutions (ITS) knows that partnering with a Managed IT Service Provider (MSP) needs to be done with complete confidence.  

To help you build confidence with your MSP, we’ve compiled 20 critical questions decision-makers usually ask and should ask when checking trustworthiness.  

Make these questions part of your routine when choosing an MSP. These will help you get the best MSP for your company.  

Company Background Questions 

Company Background Information

Company background questions are designed to help you know if you can trust your MSP. By getting a better understanding of the MSP, you’ll be able to answer the crucial question when entering a business deal: are they someone you can trust? 

Some questions you can ask to verify if a company is trustworthy are:  

1. How large is your company? 

You wouldn’t want to get into a contract with a company that overpromises but underdelivers. Therefore, you need to know how large the MSP you’re talking to is to check if they’re staffed with enough people to provide everything they promise you.  

2. How long has your company been in business? 

MSPs leverage their experience in the field to gain customers. Experience is a good indicator of their knowledge, so knowing how long they’ve been in business is a good indicator of how much an MSP can offer you.  

Of course, the length of time a business has been working isn’t everything, which leads to the next question.  

3. What are your qualifications? 

Just like you wouldn’t hire a team member if they didn’t show any ability to do the job, you wouldn’t hire an MSP that couldn’t prove their qualifications. Check if they’re a certified company and have the best qualities of an MSP. Find out what kind of training their staff has, their areas of expertise, and see if they’re a fit for your business.   

4. Do you have client stories and reviews?  

Word of mouth is still the most relied-on technique to find a service, and it would be remiss not to ask for customer experiences with your MSP. Ask to see case studies or success stories of industry companies that they’ve helped in the past. If possible, call those companies and find out for yourself whether they recommend working with this IT service provider. 

5. What kinds of services do you specialize in? 

You don’t want to sign a contract with a company that can’t help you with exactly what you need. Review what services they provide and if it matches your company’s needs; always remember that you’re hiring them, so you should take as much care as hiring a team member with hiring an MSP.  

6. What are your company’s values? 

Check a company’s values to see if they are compatible with yours. You don’t want to butt heads with people; seeing the kind of culture they have is a good starting point for evaluating your possible partnership.  

7. Are there any reasons we  shouldn’t  hire your business?  

Most companies only focus on why you should choose them. Ask this question to see if they’re willing, to be honest with you about possible faults and problems with MSPs. There’s nothing worse than false expectation setting, and if the MSP you’re talking to can answer this honestly, that’s a good sign for honesty in future transactions. 

Pricing Questions  

Weighing scale - price value

Once you know you if can trust a company, you can now ask questions about the cost of their services. Most businesses have a cost page, but before you’re ready to purchase from an MSP, it’s essential to ask more questions about the pricing.   

Some important questions to go over are:  

8. What are the prices of your services? 

Knowing how much you need to pay will help you estimate if the company fits you. If they’re too expensive, at least you know you need to find someone cheaper. Of course, most businesses will direct you to the cost page, so it’s worth checking that out and preparing company-specific questions about price before contacting the MSP.  

9. How much is your onboarding fee?  

Most MSPs have an onboarding fee that’s separate from the services they charge you for. You need to know how much this will cost you especially if you want to avail yourself of Managed IT. The onboarding fee depends on your company’s IT infrastructure, so make sure you know your IT basics: how many workstations and servers you have, what your IT goals are, and the status of your cybersecurity.  

10. Why are you charging those kinds of prices?  

If an MSP cannot justify why they’re charging the prices, that’s a big red flag, and it’s a sign of lacking transparency in the company. Of course, they’re not going to give you an entire breakdown of their company’s account and their exact profit margins, but they should be able to explain the factors that go into the MSP’s pricing.   

11. Are there any other fees connected to this service?  

It’s good to check everything you might pay for. Asking your MSP to lay out all the prices is part of building trust; this way, if they suddenly spring other expenses at you, you know price surprises are something that you’ll encounter again. Then, you’ll need to make a judgment call if they’re the kind of business you want to interact with.  

12. Will we save money with your services? How?  

Most businesses will automatically answer yes, MSPs save you money. It’s the businesses that give you good reasons why you’ll save money are the ones to trust more. Having confidence in the value of their services is a good sign for an MSP.  

Although, be cautious. You should trust but verify! Do your research about the costs of MSPs in your area before immediately committing to the first MSP you approach.  

Service Questions 

Pool of Question Mark Symbols

After clarifying concerns regarding the price of services, you need to get a good picture of what availing an MSP’s services looks like.  

Having a clear understanding of what you can expect from your MSP will help the services between you and the MSP go more smoothly. Some questions to ask about an MSP’s services are:   

13. How long does it take to complete projects?  

Asking how long they take to complete projects will help you estimate if it’s worth waiting for them to fix everything you need. Take note of the tasks you need to get done, the timeframe you need them done, and see if the MSP you’re talking to can handle the deadline.  

14. How long are onboarding and offboarding? 

Building off the previous question, knowing the length of time onboarding and offboarding takes will help you manage your schedule. Asking about onboarding and offboarding is even more important if you’re transferring from or to a new MSP.  

Onboarding usually takes a few months, while offboarding takes a month or so. Consider this in your schedule.  

15. What is your response time for critical issues? 

To succeed, your business needs to stay up and running 24/7. You can’t afford lengthy downtimes or delays. When you’re evaluating a managed IT service provider, find out how long it takes them to respond to problems and check if they can save you time 

Check their availability during business hours, late at night, on the weekends, and on holidays. If they aren’t available when you need them, look elsewhere. 

16. When can we expect onsite services?  

If you are the type of person who prefers to see people face to face, then you need to know if the MSP you have will provide onsite service again and when. Due to the COVID-19 pandemic, not all MSPs have this service. Ask this question if not having onsite services is a dealbreaker for your company.  

17. Do you provide reports for your service? 

Asking if the MSP you’re partnering with has reports will help you evaluate the services they give you. You need to check the ROI of your MSP, and different reports from MSPs will provide that.  

18. What are the different ways I can contact your customer support?  

By asking this, you’ll be able to check if you can contact your MSP properly. Efficient MSPs have different ways you can contact them and have a set process for managing your concerns. It’d be irritating to be unable to contact your MSP when you need them!  

19. What strategic IT advice can you offer for the future? 

Your business isn’t standing still, and neither are your technology needs. A managed IT service provider should look forward and anticipate the needs you will have in the future. In any conversation with IT services, talk about where your business is headed, and find out how forward-thinking they are. 

20. Should I have all my services with you? 

Like question #12, most MSPs will answer yes immediately to this question. After all, it’s easier to deal with one company than many spread-out companies. But this is one of those questions where you can see if a company will consider all your needs instead of immediately saying yes. The best MSPs will ask for context, see what they can and can’t provide, then tell you why you should be with them.  

Ready to choose the best Managed IT Service Provider for you? 

MSP maintaining a server

Remember, choosing the right MSP is integral for your business, and part of choosing an MSP is asking the right questions.  

Each kind of question serves different functions that help you evaluate a potential MSP. At ITS, we’ve noticed that clients want to be entirely at ease with us before committing to using our services.  

The questions that help customers evaluate their MSPs are:  

  1. How large is your company?
  2. How long has your company been in business?
  3. What are your qualifications?
  4. Do you have client stories and reviews? 
  5. What kinds of services do you specialize in?
  6. What are your company’s values?
  7. Are there any reasons we shouldn’t hire your business? 
  8. What are the prices of your services?
  9. How much is your onboarding fee? 
  10. Why are you charging those kinds of prices? 
  11. Are there any other fees connected to this service? 
  12. Will we save money with your services? How? 
  13. How long does it take to complete projects? 
  14. How long are onboarding and offboarding?
  15. What is your response time for critical issues?
  16. When can we expect onsite services? 
  17. Do you provide reports for your service?
  18. What are the different ways I can contact your customer support?  
  19. What strategic IT advice can you offer for the future?
  20. Should I have all my services with you?

But asking questions isn’t the only way to evaluate your MSP. Another way to vet your MSP is to perform a manual check of the ROI. Learn more about this process by reading our article “How to Determine the ROI of your MSP”.  

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