12 Questions to Ask Managed Service Providers Before You Sign on the Dotted Line

According to a 2018 report by Sage Business Researcher, the skills gap costs individual companies $800,000 annually in lost productivity costs. What is the skills gap? It is the gap between the expertise you need to operate and grow your business and the qualifications of your team or available candidates. While you may not want to hear this, technology is most likely contributing to the skills gap in your business. 

Turning to a Managed Service Provider (MSP) is one way to bridge the technology skills gap in your organization. The overarching purpose of an MSP is to monitor your environment to prevent downtime and improve your overall business structure. Working with one of the top IT managed service providers can make business management much easier for your executive team. Unfortunately, finding the right one for your needs can be difficult.  

There are many reputable MSPs that can do an okay job of managing your environment, but it’s important to find an MSP that aligns with your specific business needs. Here are 12 questions to ask your potential MSP—and yourself—when searching for an IT partner that will be a good fit for you.

1. Do Your Engineers Have Experience with a Vast Breadth of Technologies and Infrastructure Types?

Business and IT environments are becoming more and more complex. Your business probably sources technology from several different vendors, and you might have a mix of infrastructure types. While it may seem like most MSPs should be able to handle such a mix of technologies, you’d be surprised how often this is not the case. Consequently, this is one of the most important MSP questions you can ask. 

Look for a balance between breadth and depth when selecting a Managed Service Provider. You want an MSP who knows a variety of technologies and knows them well. Familiarizing themselves with all the most popular technologies is a core component of managed services best practices. 

It’s also important to confirm a potential MSP is dedicated to learning new skills and keeping themselves up to speed as technologies advance. You want an MSP that will be able to learn and help you implement new technologies as they arise.

2. Do You Outsource Your Engineering?

Many of the top IT managed service providers outsource part or all of their engineering talent. This is not necessarily a bad practice. Outsourced talent can be just as valuable as internal resources, and this can help cut costs. However, this does not work for everyone. 

If you are a business that prefers on-site support, or a smaller business without an internal IT team who cannot afford long wait times to speak to a tech, an MSP who outsources a lot of their engineering may not be a good fit for you. Before you sign a contract, make sure you know what you’ll be getting and make sure the outsourcing practices meet your needs.

3. Does Your Team Have Advanced Security Knowledge?

If you are focused on your business’s security, you may be interested in a Managed Security Service Provider (MSSP), but this is not necessary. What is necessary is ensuring your potential MSP has a firm grasp of IT and data security and is flexible enough to adapt as malicious threats become increasingly advanced. This is one of the most important questions to include on your managed services questionnaire because so much is at stake. 

You can test any MSP’s advanced security knowledge by asking them to perform a security assessment on your environment. If they cannot perform this type of evaluation and deliver polished documentation, you should look elsewhere. This is a sign that they don’t have a system established for ensuring your environment’s safety.

If you decide that an MSSP is right for your organization, the provider you select to handle the rest of your environment must understand the importance of security. A critical element of managed service provider best practices is avoiding introducing any vulnerabilities into your environment.

4. Can Your Firm Help with Upgrades or New Technology Implementations?

Not all Managed Service Providers can help you perform major upgrades or implement new technologies. Choosing an MSP who can perform complex IT projects for your business can make operations run more efficiently.

MSPs who offer IT project engineering services understand the business technology landscape more so than MSPs who only perform basic management and administrative tasks. They are also going to be intimately familiar with the technical specs of your environment as well as your business goals. This type of MSP will be strategically positioned to help you make the best decisions for your environment.

5. Do You Deliver Both Remote Management and On-Site Support?

In the modern business landscape, your business doesn’t exist inside your offices—it exists wherever your employees access your data. With the increasing popularity of working remotely and using personal or mobile devices, effective MSPs must be able to deliver their services to devices wherever they’re located.

It is possible to handle the majority of traditionally “on-site” needs remotely. Remote delivery is more efficient in terms of cost and time, and it allows you to choose your provider from anywhere in the world. This opens the candidate pool to potentially more skilled and more advanced companies. Remote delivery also positions your company for growth and expansion. If you decide to open a new office across the state or country, you’ll be confident your MSP can still support you.

While only a fraction of IT tasks cannot be performed remotely, it is still important to verify that an MSP is willing to provide on-site support when necessary. If your management is uncomfortable working with an MSP remotely, it would be better to look at providers located near your office. MSPs exist in many different shapes and sizes and deliver their services in different ways and across different locations. To ensure a successful Managed Service relationship, include an inquiry about remote versus on-site support on your list of MSP questions. 

6. Are Your Services Available 24x7x365 If I Need Them?

It is not feasible for your business to be available only during the traditional 9-to-5 work hours. Even if your employees go home at 5 p.m. each night, your customers still need access to your website or online portals, emails sent from employee devices need to be delivered, and established security measures need to function.

As part of managed service provider best practices, your MSP needs to be equipped to handle emergencies wherever and whenever they happen to get you back on track. This is why no MSP questionnaire is complete without a question about availability.

7. What Are Your Service-Level Agreements?

Service-Level Agreements (SLAs) set expectations for both you and your provider as to how long you can expect to wait when you need help and what level of service you will receive. If your potential provider does not have well-documented SLAs, it’s time to look somewhere else. This is a sign that they don’t have well-established protocols—meaning your support tickets may fall to the wayside—and they will not be consistent in their delivery.

SLAs vary between providers. Make sure you understand what falls into each of their priority levels, so you’re not left thinking your most important technologies are a Priority One when they really fall further down the list. Also, make sure the guaranteed response times fit your needs. If your business cannot wait two hours for a response time without seriously affecting your bottom line for certain tech issues, ensure your MSP has an SLA shorter than two hours. If you can get by without some systems, it may be beneficial to find a less expensive provider with SLAs that are a bit longer.

8. Are Your Services Focused on Proactivity?

If your MSP talks a lot about fixing issues quickly without mentioning any actions they take to prevent issues in the first place, they are probably stuck in the break/fix mentality. Using the break/fix method, an MSP waits until something breaks—causing downtime for your business—and then they fix it. Even if the MSP can get your systems back up and running more quickly than the traditional method of noticing and contacting, it ignores the larger problem. Your systems are still breaking.

When evaluating how proactive a potential MSP is, ask about their automation and analytics practices. Automated systems can take care of some alerting, workload categorization and prioritization, incident escalation, and remediation tasks to more efficiently uncover and address problems with your systems. Additionally, if an MSP uses analytics to improve their processes and services, it is a sign they take proactivity seriously.

It is unreasonable to expect your provider to prevent problems 100% of the time. But a quality MSP will emphasize proactivity. With a proactive approach, critical threats are identified before they affect your business, preventing downtime and interruptions in your environment.

9. Will I Have Access to Metrics on My Plan Performance and Usage?

Many of the top IT managed service providers tout their services as a “set it and forget it” style of engagement. While good managed services do prevent you from spending time worrying about technology, you should have access to detailed reports about what your MSP does on the back end to keep it that way. You should never wonder what you are paying for.

The best providers are willing to be completely transparent about their services, even if it means admitting you’re not using all of the features you pay for. This can come in the form of monthly reports or an online portal. No matter the format, make sure you’re receiving both historical problem and resolution information as well as the actions taken to proactively protect your environment.

Considering just how critical key performance indicators (KPIs) are, it’s worth adding a second part to this MSP question, and that’s, “Precisely what kinds of metrics will I have access to so I can gauge the effectiveness of our partnership?” Examples include: 

• System Uptime: The percentage of time your IT systems are operational and available for use. High system uptime is vital for maintaining productivity and minimizing disruptions to your business operations.
• Response Time to Incidents: The time it takes for your MSP to respond to and resolve IT issues or incidents. A prompt response is essential for minimizing downtime and mitigating the impact of technical problems on your business.
• Security Incident Resolution Time: In today’s cyber threat landscape, swift resolution of security incidents is paramount. Measure how quickly your MSP addresses and resolves security breaches or vulnerabilities to protect your data and systems from harm.

10. Does Your Business Have Strong Relationships with Manufacturers and Vendors? More Than One?

While your MSP plays a big part in keeping your environment functioning optimally, some problems will eventually require manufacturer or vendor intervention. A good relationship between these third parties and your provider means your MSP will be able to escalate tickets on your behalf to get answers faster than you would be able to on your own. This inside access also means they have visibility into product evolution and emerging technologies.

One way to evaluate MSPs is to ask about partner credentials. Do they have high-ranking partnerships with vendors such as Microsoft, Cisco, etc.? For example, PEI is a Microsoft Cloud Partner, which shows our commitment to our customers and partners. If a potential MSP lacks partnerships or has low-level credentials, they most likely will not be able to expedite processes or effectively manage relationships between you and your vendors.

Another thing to consider is the number of vendors an MSP works with. If they are heavily invested in a single vendor while ignoring other players in the industry, it’s likely this MSP will steer you toward their chosen vendor when it comes to making decisions. Instead, a good MSP should help you find vendor solutions that work best for your business, regardless of their established partnerships.

11. Do You Have Experience Working with Other Organizations in My Industry?

You do not want your potential Managed Service Provider to be guessing when it comes to meeting the specific needs of a business in your industry. Ask potential providers if they’ve worked with businesses like yours in the past. Better yet, ask if they are willing to provide you with references.

12. How Involved Are You Willing to Be with My Business?

Every business wants to ensure their MSP views them as a business partner rather than another paycheck. For small businesses with a tight budget looking to hire an MSP in place of an internal IT team, this question is especially important.

A strategic partner is willing to weigh in on your technology decisions—from hiring new personnel to evaluating new technologies. One thing to look for when considering new technologies is Virtual CIO (vCIO) services. A great vCIO will help you understand and make decisions for your organization.

If you’ve opened lines of communication with a potential MSP, take note of the questions they ask about your business. Do their questions focus on how much money they can make from you? Or, do they ask questions about your business goals and technology objectives? Are they trying to learn more about you personally and build a relationship? The latter questions are a good sign they are looking to form a partnership with more than your wallet and ultimately follow managed services best practices.