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“We needed to find solutions to a variety of issues whilst being a complex business, operating in a 24/7 environment. Stripe OLT listened and understood immediately the challenges we faced.”

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Simon Darley
Trusted by industry leaders

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Expert Intel

Choosing your MSP: Critical Questions you should be asking your Managed Service Provider

Published: March 27, 2024
Expert: Alex Eley
Role: Technical Director
Specialises in: Managed IT
What you will learn:
Want to know what you should be looking for in an MSP? Our Director Alex, outlines 10 key areas of exploration for IT Leaders evaluating their managed service provider.
With almost 20 years' experience and an award-winning Managed IT support team behind him, Alex knows what a good MSP looks like.

In an ever-changing tech landscape, a strong partnership with a Managed Service Provider (MSP) can be the cornerstone of a business’s success.  

Beyond basic IT support, the right MSP offers a strategic partnership that aligns with your business objectives, harnesses cutting-edge technologies, and ensures a strong cyber security posture.  

But how can IT leaders ensure their MSP is not just maintaining their environment, but proactively improving it to help drive your business forward?  

With almost 20 years’ experience operating in the MSP space, I believe there are certain questions you should be asking to critically evaluate your Managed Service Provider.  

These are my 10 key areas of exploration you should be addressing when deciding on a new MSP

1. Strategic ALIGNMENT

Assess whether your MSP aligns their approach and technology stack with your business requirements.  

Questions to Ask: 

  • How do you stay ahead of industry-specific technology trends, and how could activity positively impact our business?  
  • Do your engineers receive ongoing training and development?  
  • What technologies do you have experience with, in-house? 

Understanding how proactive the MSP is when it comes to technology their side and where their strengths lie, will give you a good idea of how they will approach your technology. 

2. Technical Expertise and Process 

Your MSP should not only resolve be able to resolve simple 1st line user requests via their helpdesk, but also help to drive innovation within your business, via more technical skillsets, such as 3rd line engineers and solutions architects.  

Questions to Ask: 

  • What’s your process internally when approaching ticket escalation?  
  • Can you provide me with an example of a project request, and not a helpdesk request? 
  • What technical roles do you employ in house that my business can benefit from? 

By asking questions that are process centric, you can ascertain how established the MSP’s offering is and how their internal workings may align with your expectations. 

3. Infrastructure and Performance 

A great MSP not only maintains your IT infrastructure but also optimises its performance, ensuring scalability and reliability. 

Questions to Ask: 

  • How do you monitor and manage infrastructure performance to prevent downtime? 
  • What strategies do you employ for capacity planning to ensure scalability as our business changes and grows? 
  • Do you manage multiple sites or am I restricted to one managed office? 
  • How can you help us get the most out of our subscriptions? 

When it comes to infrastructure, it can change quickly, so you want to establish how much support your MSP is able to provide when your needs do change. 

4. Cloud Services and Integration 

With the cloud now unquestionably integral to modern business operations, your MSP should excel in cloud management. 

Questions to Ask: 

  • What is your expertise in cloud management, and optimisation? 
  • How do you ensure seamless integration of cloud services with existing on-premises infrastructure? 
  • Do you specialise in one type of cloud technology over another? 

There are many types of ‘cloud’ and senior engineers generally specialise in one type over another. If your business is heavily reliant on Microsoft technology it’s likely you wouldn’t benefit from an AWS specialist as much as you would an Azure specialist. Establishing this is key to the support your business receives. 

5. data Management

How an MSP approaches data management, both within their business, and yours, is crucial.  Your MSP should be able to provide guidance around optimal data management practices. 

Questions to Ask: 

  • Can you support any data governance initiatives I may have? 
  • What information security and data compliance certifications do you hold? 
  • How do you manage your own data internally? 

Data management is becoming increasingly important, especially with the introduction of ai technologies. Making sure you know what you have, and where it’s located is now crucial. A good MSP will have strong Data Management capabilities. 

6. data ACCESS

As the supply chain becomes further interconnected, and in turn becomes more vulnerable to cyber attack, you need to ensure any service provider you work with, be that legal, IT, finance, etc. is operating at a secure level. As such, vetting your suppliers to understand their internal data access policies, who their suppliers are, and what systems they use, is imperative. 

Questions to Ask: 

  • Who has access to your systems, what permissions do they have and when do they have access to it? 
  • What tools do you use that can access your data externally and does it store or process any of it outside of your control? 
  • Are your users and systems and monitored by a managed security solution, like a SOC? 
  • Do users and suppliers only access your systems from managed devices? 
  • Do you adopt any specific data access controls, like a least privileged access model? 

Gaining a holistic understanding of how your suppliers operate allows you to understand where the weakest links may lie in your supply chain. 


7. Cyber Security and Compliance

In an era where cyber threats are constantly evolving, your MSP needs to take security and compliance seriously. If they themselves don’t operate a SOC (or you don’t already outsource to someone else), offering a basic level of IT security support is an essential. 

Questions to Ask: 

  • How do you minimise security risks for your clients? For example, do you require clients to turn on MFA, or carry out any patch management? 
  • Have you any experience dealing with a cyber security breach with a client? 
  • What cyber security and data security certifications do you hold? 
  • What cyber security services are you able to offer me? 

In establishing how robust your MSPs security offerings are, alongside their own certifications you can begin to build a picture around how seriously they take security. 

8. Automation and AI (Artificial Intelligence)

Automation and AI are key technologies that allow MSPs to deliver quicker and smarter solutions, but with an unregulated and new technology era comes unknown risks. You want to make sure all the PII (Personally Identifiable Information) you have in your systems (such as on support tickets) aren’t being put in to open AI tools that can be accessed by anyone. One of the problems with AI is that you can’t purge your data once it’s ingested in most systems. 

Questions to Ask: 

  • Do you use AI, if so, is it private or public instance and how do you control what goes into it? 
  • How do you manage your automations internally? 
  • How do you control the permissions of the AI or Automations, that have access to your systems? 

AI and automation can be extremely useful, but if they are not managed correctly, they come with risks – risks that your MSP needs to have prepared for. 

9. Reporting and Management

Making sure your MSP regularly reports back on activity is crucial to a successful partnership. If visibility over the service is a priority to you, you should ask the following questions similar to the following. 

  • How often do you provide reports, are they on a monthly, quarterly or annual basis? 
  • Ideally I’d like a consistent point of contact, do I get an account manager? 
  • What format do I receive reports in? Are these over Teams, Face to Face or just over email? 

Setting expectations and knowing what you need before a service is delivered is crucial to a successful partnership. 

10. Long Term Strategy

If recent global events have taught us anything, it’s that being dynamic in business is essential. So, ensuring your MSP can support both your immediate needs and long-term ambitions is crucial. Ask the following questions to understand if your partnership will enable dynamicity or hinder it. 

  • What are your policies and practices regarding customer support and communication, especially during critical incidents? 
  • Can you explain your pricing model and how it accommodates growth or changes in service needs? 
  • What’s your current approach to ai? 

Choosing the right MSP goes beyond finding a service provider; it’s about selecting a partner that can propel your business forward. By asking the right questions, you can uncover an MSP’s true capability to support your business goals, drive innovation, and ensure a secure, efficient IT environment. 

For IT Leaders searching for IT support, consultancy and guidance, our award winning team are here to help. Get in touch today.

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