12 Questions to Ask Your MSP Before You Sign on the Dotted Line

Evaluating Managed Services Providers

According to a 2018 report by Sage Business Researcher, the skills gap costs individual companies $800,000 annually in lost productivity costs. The skills gap is the gap between the expertise you need to operate and grow your business and the qualifications of your team or available candidates.

One area most likely contributing to this gap in your business is technology. We’re all tired of hearing this, but technology is advancing more quickly than ever before. This means that while tech is capable of achieving more than ever before, your IT team is most likely having a tough time keeping up. This combined with the modern accessibility of technology—meaning smaller businesses are now able to take advantage of some of the most powerful tech solutions—means there is an unprecedented number of organizations who could use some help.

Using a Managed Services Provider (MSP) is one way you can address the technology skills gap in your organization. You can use an MSP to handle any aspect of your technological environment—cloud computing, networks, data storage and backup, communication, security, disaster recovery, mobility, end user support, and more. The overarching purpose of an MSP is to handle alerts, patch management, problem resolution, and proactive issue prevention. This means they’re managing and carefully monitoring your environment to prevent downtime and improve your overall business performance.

MSPs can make business management much simpler for your executive team. Unfortunately, finding the right Managed Service Provider for your needs can be an extremely difficult task, and you often don’t know if you’ve made a bad choice until after you’ve signed a contract and your business is on the line. While there are many reputable MSPs out there that can probably do an OK job of managing your environment, it’s important to take note of the specific needs of your business since not all MSPs are a good fit for all types of organizations.

If you’re an international enterprise with major operations in multiple countries, you might prefer an MSP with an international physical presence that offers language support for each country you operate in. A company like this probably outsources many of their engineers, but this can help you cut costs while finding someone who can support you in several languages. On the other hand, a midsize business housing their main operations in the US with a smaller presence internationally might prefer a smaller MSP that doesn’t outsource any engineering talent.

There are a lot of details like outsourcing and physical location to keep in mind while trying to locate the specific provider that will make the most sense for the unique needs of your business. Here are 12 questions to ask your potential MSP—and yourself—when trying to find 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 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. It may seem like most MSPs should be able to handle a mix of technologies, but you’d be surprised how often this is not the case.

It’s also important to find out if a potential MSP is dedicated to learning new skills. This is a good sign that your MSP will keep themselves up-to-speed as technologies advance and will be able to learn and help you implement new technologies as they are developed.

Keep Your Business Flexible

Any provider you’re evaluating should be able to work with both on-premises infrastructure as well as with public, private, and hybrid cloud environments. Even if your business operates completely on-premises due to regulatory requirements in your industry or the preferences of your IT manager, using an MSP provider with cloud capabilities gives your business flexibility in the event that the cloud becomes a feasible option for your business—and vice versa if you’re operating solely in the cloud and suddenly need on-premises infrastructure.

Choosing an MSP with a wide breadth of experience means you won’t need to find a new provider each time your business grows and adds a new element to your environment. The same principle applies to technologies and vendors. As technology continues to advance, you don’t want to be limited by the capabilities of your MSP.

Finding a Balance Between Depth and Breadth

There are many types of Managed Service Providers. Some of these providers offer to help maintain and optimize your entire technology landscape while others focus on delivering highly advanced expertise for just one specific aspect of your business. One of the most popular examples of the latter is a Managed Security Service Provider (MSSP). It can be tempting to start looking for distinct, more advanced MSPs to handle each tiny piece of your environment. Unfortunately, this can have negative effects by making your environment too fractured where the MSPs don’t communicate well or overlap enough. These technology silos can make your business too rigid and inefficient whereas one primary goal of your MSP should be to make your business run more smoothly. This method is also much too expensive for a majority of organizations where this level of granular management is unnecessary.

The best solution is to make sure the company you’re evaluating doesn’t fall too far on the other side of this spectrum and finding a balance between the number of different technologies your MSP will be able to touch and how well their engineers know each of them. MSPs who are generally familiar with many different systems but only offer basic operating system maintenance and availability management will not be able to provide the more advanced skills that bridge the gap between keeping systems online and providing extra value to your business.

Of course, this methodology won’t work perfectly for every organization. While it’s a good general rule to use as few MSPs as possible to provide thorough coverage for your business, there are some cases where you might consider more than one. If your business is especially reliant on one piece of your environment, it may make more sense for you to find a dedicated MSP for that piece of technology—even if they can’t help you with other elements—and use another MSP for the rest of your environment.

An example of this might be a customer service organization that relies entirely on their phone system being operational for their business to operate. Such a high level of reliance on the availability of their phone system—like Skype for Business—might warrant looking for an MSP that can manage this application more in-depth than a less-skilled MSP who has general experience with phone systems but is a good fit for the rest of your environment.

Make Sure Skilled Engineers Will Be Available When You Need Them

The most skilled engineers at any MSP are likely to be the busiest individuals at the company. Ask any potential MSP about the availability of engineers with certain skill sets—especially for critical or uncommon technologies. They might boast about their SCCM expertise, but if they only have one SCCM engineer who’s constantly inundated with tasks, he or she might be too busy to get to your environment consistently or quickly in emergencies. In this example, you’re not really getting access to expertise you’re paying for.

Engineers at an MSP will always be busy, so don’t fret too much if you hear this. It’s also not time to run away if you hear they only have one engineer for a certain, highly-advanced technology. This is an area where you need to evaluate your business needs. An enterprise may want the assurance of having dozens of engineers able to handle specific pieces of their environment, while a smaller company might want to save money by finding an organization with fewer engineering staff members to contribute to overhead. One thing to keep in mind is that it’s not necessarily the number of engineers available at any given time that’s important.

It’s more important to understand how the company handles resource constraints when there are urgent threats or problems. Make sure to ask your potential MSP about their standard operating procedure for addressing issues and how quickly you’ll be able to receive help in an emergency from an engineer with the specific skills corresponding to your environment. A well-managed MSP will have an established plan for ensuring emergencies are always handled efficiently by the most relevant engineer. Also investigate how much time knowledgeable engineers will be able to spend on your environment for proactive measures. This will help you get a feel for how well your more advanced systems will be handled.

2. Can your Firm Help with Upgrades or New Technology Implementations?

Not all Managed Services Providers have the ability to help you perform major upgrades or implement new technologies, but choosing an MSP who can perform complex IT projects for your business can make operations more efficient.

MSPs who also offer IT project engineering services understand the business technology landscape more thoroughly than MSPs who are only able to perform basic management and administrative tasks. They also are intimately familiar with not only the technical specs of your environment, but your business goals as well. This type of MSP will be strategically positioned to help you make the best decisions for your environment.

3. Do You have Experience Working with Other Organizations in my Industry?

You don’t want your MSP 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 any businesses like yours in the past. Better yet, ask if they’re willing to provide you with references.

4. Does your Team Have Advanced Security Knowledge?

While it may not be necessary for most businesses to find themselves a Managed Security Services Provider (MSSP), it’s essential that your MSP has a firm grasp of IT and data security and is flexible enough to adapt as malicious threats become increasingly advanced.

It’s common for smaller businesses to think they’re small fish for hackers compared to enterprise powerhouses and the massive amounts of data they store. This is an unfortunately common misconception. The 2018 State of Cybersecurity in Small and Medium Size Businesses conducted by the Ponemon Institute found that 67% of SMBs experienced a cyberattack in the previous 12 months alone with the average cost to remediate a breach at $383,365.

The Ponemon Institute also found in their study that 67% of data breaches were due to employees using weak passwords that were easily compromised. Your MSP should be able to set and enforce a strong password policy for your organization as well as handle more intricate network security configurations and data protection policies.

A good way to test this is to ask any MSPs you’re evaluating to perform a security assessment on your environment. If they aren’t able to perform this type of evaluation and deliver polished documentation, there’s a good chance they don’t have an established system for ensuring your environment is as safe as it could be.

Even if you do 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 and how they can prevent themselves from introducing any vulnerabilities into your environment.

5. How Involved are You Willing to be with my Business?

This question is especially important for smaller businesses looking to hire an MSP in place of internal IT resources due to a tight budget, though every size of company should make sure their MSP views them as a business partner and not simply another paycheck.

A strategic partner will be willing to weigh in on your technology decisions—from hiring new personnel to evaluating new technologies. Look for businesses offering Virtual CIO (vCIO) services. These include participating in important meetings, offering strategic insights, helping you make the best decisions, and more. Most importantly, this doesn’t mean that your MSP keeps all knowledge about your environment to themselves. Instead, a great vCIO will help you understand what’s happening in your organization. One way they might do this is by providing you with reports that help you understand your environment and make decisions in tandem with your provider.

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 only on how much money they can make from you? Or, do they ask questions about your business goals or technology objectives? Are they trying to learn more about you personally and build a relationship? These latter questions are a good sign they’re looking to form a partnership with more than your wallet.

6. Will I Have Access to Metrics on my Plan Performance and Usage?

Many MSPs tout their services as a “set it and forget it” style engagement, and while good managed services do prevent you from spending time worrying about technology, you should have access to detailed reports about what your MSP has been doing on the back end to keep it that way. You should never wonder what you’re paying for.

The best providers are willing to be completely transparent about their services—even if it means admitting you’re not using many of the features you’re currently paying for. This can come in the form of monthly reports or an online portal. Whichever format you receive this information in, make sure you’re receiving both historical problem and resolution information as well as the actions taken on your environment to proactively prevent issues.

7. What are Your Service-Level Agreements?

Service-Level Agreements (SLAs) set expectations for both you and your provider of how long you can expect to wait when you need help and what level of service you will receive. If your potential provider doesn’t have well-documented SLAs, then it’s time to consider another choice. This is a clear sign that they don’t have established protocols—meaning your support tickets might fall to the wayside—and also that they won’t be consistent in their delivery.

SLAs vary widely between individual 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 farther down the list. Also, make sure their guaranteed response times fit your needs. If your business can’t wait two hours for a response without seriously affecting your bottom line for certain tech issues, make sure your MSP has an SLA shorter than two hours. If you can get by without some systems, it may be in your best interests to find a less expensive provider with SLAs that are just a bit longer.

8. Do you Deliver both Remote Management and On-site Support?

In the modern business landscape, your business doesn’t just exist inside your offices—it exists where ever your employees access your data. With the increasing popularity of working in remote locations or using personal or mobile devices, an effective MSP must be able to deliver their services to devices wherever they’re located.

It’s also possible to handle the vast majority of traditionally “on-site” needs remotely. This delivery method is more efficient in terms of cost and time as well as allows you to choose your provider from anywhere in the world—opening up the candidate pool to potentially more skilled and advanced companies than are available in your locale. Remote delivery also positions your company for growth and expansion. If you open a new office across the state or country, you’ll be confident your MSP can follow you there.

Conversely, although only a tiny fraction of IT tasks are not able to be performed remotely, it’s still essential to verify that an MSP is willing to provide on-site support when absolutely necessary. This is another area where the best type of MSP for you will depend on the specific needs of your organization. If your management is uncomfortable working with your MSP remotely, it would be better to pursue an organization located near your business. If your organization exists in multiple countries, you might prefer a large MSP with offices located all over the world. MSPs exist in many different sizes and are able to deliver their services in a variety of ways—finding one that will work with your preferences is important to ensuring success.

9. Are your Services Available 24x7x365 if I Need Them?

In the modern business landscape, it’s not feasible for your business to only be available during the traditional 9–5 work hours. Even if your employees go home at 5pm each night, your customers still need access to your website or online portals, emails sent from employee mobile devices need to be delivered, and established security measures need to be functioning.

Your MSP must be able to handle emergencies whenever they happen to get you back on track.

10. Are Your Services Focused on Proactivity?

If your MSP talks a lot about fixing issues quickly without mentioning the actions they will take to prevent issues from happening in the first place, this is a sign they’re stuck in the break/fix mentality. With the break/fix method, your MSP waits until something breaks—causing downtime for your business—and then they fix it. The problem with this method is your systems are still breaking, even if this MSP can get them back up more quickly than the traditional method where you need to notice and then call IT Support.

Although it’s unreasonable to expect your provider to prevent problems 100% of the time, a quality MSP should emphasize proactivity—preventing problems and driving continuous improvement. With a proactive approach, critical threats are identified before they affect your business. This prevents you from experiencing downtime or interruptions in service, and this type of MSP also provides much more value by continually working on your systems instead of waiting for an S.O.S. alert before taking any action.

When evaluating how proactive any potential MSP is, ask about their automation and analytics practices. Are they using automation to reduce the need for human intervention? Automated systems can take care of some alerting, workload categorization and prioritization, incident escalation, and remediation tasks to address problems with your systems much more efficiently than procedures that rely on a person to notice and then address the problem. Additionally, are they using any analytics to improve their processes and deliver more reliable service? This is a sign they take proactivity seriously and aim to provide the most efficient experience possible.

11. Does Your Business Have Strong Relationships with Manufactures and Vendors? More Than One?

While your MSP is a big part of 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 the 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. This knowledge will help you make strategic decisions for your environment and maybe even snag a discount or two.

One way to evaluate MSPs in this area is to ask about partner credentials. Do they have high-ranking partnerships with important vendors like Microsoft, Cisco, etc.? If a potential MSP doesn’t have any of these partnerships or has only very low-level credentials, they are most likely not going to be able to expedite processes or manage the relationship between you and your vendors.

Another thing to take note of is the number of vendors your potential MSP works with. If they are heavily invested in a single vendor while completely ignoring all other players in the industry, it’s likely this MSP will try to steer you towards their chosen vendor when it comes to making strategic decisions. Your MSP should instead help you find the vendor solutions that work best for your business—regardless of their established partnerships.

12. Do You Outsource Your Engineering?

Many of the largest MSPs outsource part or all of their engineering talent. This is not necessarily a bad practice as outsourced talent can be just as valuable as internal resources and this can help cut costs. However, this may not work for everyone, especially businesses that prefer on-site support or smaller businesses without internal IT resources who can’t afford long wait times to speak to a tech. Before you sign a contract, make sure you know what you’ll be getting and decide whether their outsourcing practice meets your needs.

So, Where Do You Start?

If you’ve made it to the bottom of this very long page, you’ve probably learned that selecting an MSP isn’t as simple as running them through this list of questions. While these questions will provide a sturdy base for evaluating any MSP on your radar, the most important pieces of the relationship between you and your MSP are the health and needs of your business. After all, your choice to find an MSP means you’re invested in protecting your business against downtime and other problems caused by not having your IT situation completely figured out.

Need a basic first step? Start with PEI. We’re an award-winning Managed Services Provider and we’re happy to answer all of the questions on this list for you. Contact us to learn more!

Stephanie Hamrick, PEI

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