by Scott Jack
Content Contributor, E-N Computers
15+ years of experience in systems administration including endpoint management, application deployment, and documentation.
There are dozens of articles telling you what to ask when shopping around for a new MSP, like questions around response time, pricing, and security. You probably have a good idea of what technology you have, too. But it can still be a challenge to know when you’ve found the MSP that’s the right fit for your business.
In our experience, that’s because online articles encourage buyers to obsess over technical questions and checkboxes, which causes them to lose sight of the bigger business picture.
“I find that usually the buyers are so focused on the technology, to the point where they’re missing that this is also a relationship,” said Ian MacRae, president of E-N Computers. The questions that predict whether an MSP will work for you are less about tools and more about ownership, structure, and how a company actually operates day to day.
So here’s our insider take on what matters most, pulled from what MacRae hears in his conversations with prospects and clients.
QUICK ANSWER:
What are the most important questions to ask an MSP before signing?
When evaluating MSPs, the most important questions focus on ownership structure, account management, pricing transparency, and operational fit. Rather than focusing solely on software features and response-time metrics, ask about owner stability, dedicated vs. shared account managers, integrated vs. line-item tool pricing, and hands-on audit prep experience to ensure they fit your long-term business goals.
Pay attention to ownership, structure, and fit
Every vendor relationship has friction: a late invoice, a bill you don’t fully understand, or a slow week. Those things happen, and they’re poor reasons to end a partnership. But, MacRae says, it’s fair to consider changing MSPs if they can’t keep up as your business grows.
To figure out how likely that is, find out about ownership, structure, and fit. Here are some questions you may want the answers to:
- What’s the ownership structure? Is it a standalone company or a subsidiary? In the MSP industry, many subsidiaries are once-independent IT companies that have been bought out. The team might be the same, but their parent company calls the shots on staffing, pricing, and tools, giving them less flexibility than an independent MSP.
- Does the owner plan to sell or retire? If they’re an independent MSP, you want to know what kind of risk there is of them losing their independence. An MSP transition can be rocky, even when it is because of an acquisition or merger.
- Do they assign a dedicated account manager that is separate from the service team, or one person that does it all? This is about how work is organized. Some MSPs give you one person that’s responsible for all of your support and account management. Others have a business account manager, technical account manager, and service team. Or, you may not have an assigned team at all, especially if they’re mainly providing you with access to a helpdesk.
- Is the MSP growing, or a steady size? Some MSPs experience growing pains that impact service delivery, but that growth also comes with a greater capacity to serve growing businesses. Other MSPs stay at a pretty consistent size, have core long-time clients, and relatively low turnover. Neither is inherently better, but one might be a stronger fit for your business.
- How process-driven are they: is there a lot of bureaucracy or is it laid back? A compliance-heavy business needs a provider comfortable with process and audit trails. A business that doesn’t want to file a ticket for every request needs something closer to a one-person shop.
The same idea applies to all the other common questions to ask MSPs: they’re technical questions, but what you really need to look for is how they operate and think about things. Sometimes the right answer is more about what you want out of the partnership, and less about an objectively correct way of operating.
Response time and SLAs
You know to ask about service level agreements, or response times, and most MSPs are going to have one written down. But will they meet it?
“I think what people are really asking is: are you going to be able to be responsive when I need you?” MacRae said. He compares it to calling Comcast. When you call, you’ll eventually get someone on the phone. But it’s always a different person. They meet their metrics, but your experience is terrible because there’s no one following through on your issues.
What you really need to know is how the team is structured to provide a worthwhile response before you need to think about whether they’re meeting an SLA. Who is assigned to your account? How do they make sure that issues are followed through to completion? What is their process for identifying and permanently fixing a recurring problem?
Look for continuity of service. You want the same person or team involved from beginning to end so that they know your account and can make sure tasks are fully completed.
Pricing transparency: what the quote structure tells you
MacRae pushed back on the idea that most MSPs are deliberately hiding their pricing. “I don’t see a lot of purposeful obfuscation, but I do see different strategies,” he said.
Some MSPs bring their own suite of tools for device management, spam filtering, and backup. Others build around Microsoft’s own licensing and hand you the keys to keep it. Tool-heavy quotes are easier to read line by line, since every cost is itemized. But a quote listing ten separate tools can still miss features a single Microsoft Business Premium license already covers. And if you ever change MSPs, or your MSP is acquired by another company, you’ll be looking at changing all those tools out, making switching more complicated.
If you’re considering an MSP that uses an integrated approach like relying on Microsoft tooling, ask them to provide the pricing on licensing. This will give you a clearer idea of your total recurring cost. Keep in mind that you’re likely getting more, better integrated features for that price. If you have any questions, don’t hesitate to ask for clarification.
Ask questions to make sure you understand what you’re getting for the price. Many MSPs sell access to a help desk and call it managed IT. But they don’t have engineers reviewing your systems for potential or recurring problems, they’re not having regular strategy discussions, and they’re not doing compliance work. Find out if their system is ‘open a support ticket and we’ll take care of it’, or whether someone is assigned to proactively look at your systems and address potential problems. Whether you want helpdesk-only, or a fully managed strategic partner, make sure of what you’re paying for.
Read more about what managed IT services should cost.
If you need CMMC support, know their audit prep experience
Ask any MSP working with defense contractors if they’ve taken a client through a CMMC audit, and most will say yes. But what does that involve, exactly?
Even though the requirement to pass a third-party assessment is suspended, MacRae cautions against taking this as permission to attest to compliance without doing the work. He likens the difference to having an old car versus having one that is registered and insured.
Self-attesting to security controls is like owning an old car and saying it has airbags, seat belts, and bumpers. While all those things may be true, none of it means the car is licensed, insured, or road-legal. “Then what is actually passing an audit? Getting all of the paperwork right — the policies, the incident response — and now for an audit we actually have a log book and can demonstrate the maintenance is taking place,” he said. To pass an assessment, you need to be able to produce current evidence — screenshots, logs, documentation — that the controls are in operation, not just installed once. And you should be ready to pass that audit at any time, whether or not regulators currently require one.
MacRae said audit prep at E-N Computers, a CMMC Registered Practitioner Organization, runs around $10,000 and roughly 40 hours of intensive work, because every piece of evidence has to reflect the system’s current state — nothing older than 90 days.
Related reading: Do you need GCC High?
Get a ballpark estimate
Most MSPs will give you a ballpark figure of what services are likely to cost based on your industry and size.
“I always give ballparks. Ballparks are quick, off the cuff. I try to get them back to you the same day, same week, same call,” MacRae said. For managed services specifically, a provider can get close fast, since the inputs are things a business owner already knows: number of computers, number of employees, current Microsoft licensing. Project work is harder to ballpark, since it depends on hardware, timing, and scope. For projects, an MSP may require a short paid discovery phase before giving a quote.
If you’re reading this after you’ve already signed
If you wish you had found this article earlier, before you chose your current MSP, it’s not too late to cut your losses. Start by figuring out what your contract actually says about exit terms and data ownership: Here’s how to end an IT MSP contract.
If you want to compare our answers to the questions above, schedule a complimentary consultation with E-N Computers.
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