How Do I Know an MSP Is Right for Me?

Once you are comfortable with the integrity and ethics of the MSP (Managed Service Provider), and you are confident the provider can fulfill your basic needs to your satisfaction, there are still more factors to consider. The next layer of evaluation is centered around your desired outcomes and how you will evaluate the quality and value of the provider against those expectations.

How do they deliver?

You will be presented with many appealing features of the MSP’s service offering during the sales process. Features that are difficult to quantify—such as “understanding your business, integrating with your business, being an extension of your team, and creating a partnership with you”—are high on the list. Proactive services that are often touted can include “eliminating the worry in IT, proactively managing and monitoring your technology, and preventing problems before they happen.” The most powerful question in your arsenal as a customer is “how”? For each unquantifiable feature offered, you should question how they deliver that service demand. Without specific, detailed answers as to how these obligations are fulfilled, both parties end up relying on wishful thinking and false optimism.

Know the MSP lingo

There are several words and phrases that you will need to be familiar with while shopping for an MSP. There’s all the usual technical speak and acronyms that are common when engaging in a business technology conversation. There are also some terms that are overused and misused in the MSP industry that you will need to be prepared for: “proactive,” “strategic,” and “trusted advisor.”


Proactive is the most overused word in the MSP industry by a long shot. After all, it is a great word that we typically understand as “being saved from something painful before it happens.” Who doesn’t want that? There are nuances within the MSP industry of how the word proactive is defined in relation to the services provided. Proactivity is often associated with monitoring tools that are deployed in an environment to detect certain events and conditions. When something is detected, an alarm or alert is sent to the MSP for them to act upon. This is where the nuance in interpreting the definition of proactive comes in. Our take is that “responding to it after it has happened” is in direct contradiction to being “proactive”.

There’s no doubt that being proactive is a paramount concern; how the MSP is “proactive” within the true definition of the word is critical. The textbook definition is:

“(of a person, policy or action) creating or controlling a situation by causing something to happen rather than responding to it after it has happened.”

The first step in evaluating whether a provider is truly proactive is to have clarity on the accurate definition of “proactive” services and then ask the provider what in their offering they consider fitting this definition. Don’t tip your hand in this scenario by defining the term for them, as their answer will reveal the provider’s true interpretation of its meaning. Thereafter, ask “how” the proactive services they listed are delivered. Again, demand specifics and details.


Strategic is the next MSP term you should be familiar with. Often paired with “partner,” being strategic without structure is just an ambiguous promise. The textbook definition is:

relating to the identification of long-term overall aims and interests and the means of achieving them.”

MSPs have huge variations in how they achieve being “your strategic partner” and you will need to carefully consider and evaluate what is right for you. What is important to keep in mind is your desired outcome. What specifically do you want out of the relationship with your MSP, and how does that outcome integrate with your company’s plans, initiatives, and goals?  You know your business best, and how an MSP integrates (another overused word) is critical to achieving your business objectives. Some good questions to ask are:

  • How is the MSP strategic, and what does their process look like with specifics and details?
  • How do they investigate your company and discover your challenges, hopes, wishes, desires and opportunities?
  • How do they arrive at their recommendations considering your business objectives and tie that information back to your technology plan?
  • What is their method and rhythm of communication and collaboration with your core leadership team and staff members?

Trusted Advisor

Trusted Advisor is the last term you should familiarize yourself with. It’s an easy and convenient way to pitch yourself as the type of person or entity that a prospective client should do business with. The problem with this term is that you should expect much more than just someone you trust to solve your problems. Your trusted advisor should be your methodical, technical advisor who understands your business, challenges, and initiatives. You can quickly determine which type of advisor you have by asking yourself a few key questions:

  • Do you only turn to your “trusted advisor” when you need basic IT advice (such as when you should upgrade software or hardware)?
  • Is your relationship with your provider or IT person based more on how much you like them instead of the quality business advice or insights you receive from them?
  • Does your “trusted advisor” take the initiative to meet with you or your executive team on a regular basis, and are they knowledgeable about your business?
  • Do they understand your business strategy and the role technology plays in enabling your plan?

Cultural Fit

Integrity and ethics are of paramount importance in the MSP industry. Much like automobile mechanics and general contractors that perform services which consumers are unlikely to fully understand, trust and integrity are essential to avoid deception and fraud. Mega-companies like Office Depot have utilized scrupulous business practices to defraud consumers by manipulating or misrepresenting technical issues. When checking the MSPs references, ask questions regarding the major projects delivered by the MSP and whether they received the value they expected from those capital investments.

Another critical consideration is the cultural fit between you and the MSP. Does the MSP align with the core values of your company and stand for similar ideals? Cultural fit is an essential element of a mutually beneficial long-term relationship. Each MSP has a unique culture that may or may not mesh with yours, and this should be carefully considered when selecting an MSP.

In addition, it may help to ask: What does the MSP require of your internal staff, and how do they interact with them? The frequency and duration of effort from your internal staff to assist or collaborate with the MSP is important to consider in your overall cost and ROI. Example touch points are:

  • How does the MSP assist with onsite troubleshooting or fixes if/when they are unable to send someone to you?
  • How available does your staff need to be to the MSP if/when they are onsite?
  • How frequently do you need to meet with the MSP to stay informed, and what is their method and process to communicate with you?
  • How much of the legwork are you going to need to do for what the MSP cannot or will not fulfill?

It can be difficult to evaluate these things during the sales process but asking questions that paint a picture of a real-life scenario can reveal the extent of additional charges, work your staff will need to perform, and to what degree you will need to manage the provider.

Trust Your Instincts

Ultimately, you will need to trust your instincts and decide whether the provider fits your requirements, whatever they may be. This article is intended to inform you of important aspects you should consider but is not all-inclusive. Although most MSPs offer the same core services and messaging, they are not all created equal.