Choosing a managed IT provider can be surprisingly difficult because, on the surface, many IT companies sound almost identical. They offer help desk support, cybersecurity, Microsoft 365, cloud services, monitoring, backups, and some form of strategic technology guidance.
Those services matter, but they don't necessarily tell you what it will be like to depend on that company.
For a NonProfit with 20–100 employees, we believe leadership should evaluate a managed IT provider across six areas: responsiveness, cybersecurity, NonProfit understanding, strategic guidance, transparency, and continuity.
The objective isn't simply to find a company capable of fixing computers. It's to find a technology partner that understands how your organization operates, supports employees when they need help, protects the organization from growing cyber risk, and helps leadership make better technology decisions over time.
A useful question to keep in mind throughout the selection process is:
Will this provider understand our organization well enough to protect it, support our people, and help us make better technology decisions?
1. Responsiveness: What Happens When an Employee Needs Help?
Every IT provider will tell you that it provides support. What matters is what that support feels like when an employee needs it.
Imagine that one of your program employees can't access an application they need to serve a client. Your bookkeeper can't use the computer needed to complete an important task. An Executive Director is preparing for a board meeting and suddenly can't access a document. Or an employee clicks something suspicious and needs immediate guidance.
How easy is it to get help?
The answer isn't found only in a service-level agreement. Leadership should understand how employees contact support, whether they can reach a real person when appropriate, what happens when the first technician can't resolve an issue, and whether the provider develops enough familiarity with the organization to understand how employees work.
That last point is easy to underestimate.
Good support isn't simply closing tickets. Over time, the IT provider should begin understanding the people behind those tickets.
Heidi Maderia, Executive Director of the Association for Infant Mental Health in Connecticut, described this difference after I-M Technology took over her organization's IT support. She said getting a live person quickly made a significant difference, while employees no longer had to waste time navigating layers of requests and downtime declined.
But one of the most revealing examples she shared was much smaller.
When replacing a computer for the organization's bookkeeper, the I-M Technology team anticipated that the employee would benefit from a machine with a numeric keypad.
That's not a sophisticated technology project. It is, however, an example of an IT company understanding that technology exists to help a particular person do a particular job.
When you're evaluating an MSP, don't ask only how quickly tickets are answered.
Ask whether the provider's support model is designed around your employees being able to get their work done.
2. Cybersecurity: Is Security Part of the Relationship or an Afterthought?
An organization can have responsive IT support and still have inadequate cybersecurity.
That's why cybersecurity should be evaluated separately when selecting an MSP, particularly for health and social-services NonProfits that may work with sensitive client information, remote employees, mobile devices, cloud applications, or compliance-related requirements.
Leadership doesn't need to compare every security product used by competing providers. In fact, a long list of technical tools can sometimes make an evaluation more confusing rather than less.
Instead, consider cybersecurity through four responsibilities:
Prevent → Detect → Respond → Recover
How does the provider help prevent common threats? How does it identify suspicious activity or emerging problems? What happens when a security event occurs? And if an attack causes disruption or data loss, how does the organization recover?
Those four questions are more useful than simply asking whether an MSP “does cybersecurity.”
They also reveal whether security is integrated into the provider's approach to managing IT or treated as a collection of optional products added after the basic support agreement is signed.
A provider should also be able to explain cybersecurity in language leadership understands. Your Executive Director doesn't need to become a security engineer, but leadership should understand the organization's largest risks, what is being done about them, and where additional action may be necessary.
I-M Technology addresses these responsibilities through its SecureIT Managed Cyber Security services, but regardless of which provider you're evaluating, the principle is the same: cybersecurity should be an ongoing responsibility, not something discussed only after an incident.
3. NonProfit Understanding: Does the Provider Understand How Your Organization Makes Decisions?
There is a difference between providing IT services to a NonProfit and understanding how NonProfits operate.
Technology decisions inside a NonProfit may need to account for program priorities, funding cycles, boards, grants, limited resources, sensitive client information, employee capacity, and the responsibility to use donor or public funds thoughtfully.
That context matters.
Suppose an aging piece of technology could be replaced today but can also continue operating safely for another year. A provider focused primarily on selling technology might recommend replacing it immediately.
A strategic partner should be able to explain the risks and tradeoffs and help leadership determine whether replacing it now is genuinely the best use of the organization's resources.
Sometimes the correct recommendation will be to make the investment immediately because the operational or security risk is too high.
Sometimes the correct recommendation will be to wait.
A provider that understands NonProfits should be comfortable with both answers.
The Coast Guard Foundation offers a good example. When I-M Technology helped modernize the Foundation's technology environment, the approach wasn't to replace everything at once. Existing investments were considered, and older servers were allowed to reach end-of-life before the organization gradually transitioned those systems to the cloud.
That doesn't mean delaying every technology investment is good stewardship.
It means good IT strategy should help leadership understand what needs attention now, what can safely wait, and why.
For NonProfits, that's an important distinction.
4. Strategic Guidance: Does the MSP Have a Plan Beyond the Help Desk?
Help desk support solves today's problems.
Technology strategy prepares for tomorrow's.
As a NonProfit grows, leadership shouldn't discover major technology needs only when something breaks or a new requirement suddenly appears.
Your IT provider should be capable of looking 6- 12 months ahead and helping leadership understand what is coming.
That may include aging computers and infrastructure, cybersecurity priorities, cloud services, software changes, backup and recovery, new programs, organizational growth, remote work, mobile devices, or technology investments that need to be anticipated.
This doesn't require the Executive Director to sit through a highly technical presentation every month.
It requires the provider to translate technology into decisions leadership can understand.
One question worth asking a prospective MSP is:
“If we hire you, what should our leadership team understand about our technology 12 months from now that we don't understand today?”
Listen carefully to the answer.
If the conversation immediately returns to products and technical specifications, you may be talking to a technology vendor.
If the provider begins discussing risk, priorities, organizational goals, lifecycle planning, employees, and how technology supports the mission, you may be talking to a strategic partner.
That difference becomes increasingly important as the organization grows.
5. Transparency: Can They Explain Why They're Recommending Something?
Technology can be intimidating, and that creates an unhealthy dynamic when leadership feels it has no choice but to approve whatever the IT company recommends.
A good provider should never require blind trust.
Instead, important recommendations should be explainable through a straightforward framework:
Problem → Risk → Options → Recommendation
What is the problem?
What happens if the organization does nothing?
What reasonable options are available?
Why is the provider recommending one option over the others?
Leadership doesn't need every technical detail behind the recommendation. It does need enough information to make an informed decision.
This is particularly important when the organization is considering a major equipment replacement, cloud migration, cybersecurity investment, or other project requiring significant resources.
Transparency also means being willing to say when something doesn't need to be purchased.
If an existing system can safely continue operating, leadership should know that. If delaying an investment creates an unacceptable risk, leadership should understand that too.
Trust develops when recommendations consistently make sense in the context of the organization's needs—not merely the provider's services.
6. Continuity: Are You Hiring One Technician or an Organization?
Relationships matter in IT.
It's valuable when employees know the technician who regularly helps them and when that technician understands the organization's environment.
But familiarity shouldn't create another single point of failure.
Ask what happens when your usual technician is sick, on vacation, working on another emergency, or leaves the provider entirely.
Can someone else step in?
Is your technology environment properly documented? Are important credentials appropriately managed? Does knowledge about your organization exist somewhere besides one technician's memory?
There is another continuity question that's equally important but sometimes uncomfortable to ask:
What happens if we eventually decide to leave the MSP?
Your organization should remain in control of its technology environment.
A healthy IT partnership shouldn't depend on withholding documentation, credentials, or institutional knowledge in order to make changing providers unnecessarily difficult.
The best provider relationships are retained because clients continue seeing value—not because leaving feels impossible.
Should a NonProfit Choose an MSP Based on Price?
Price matters. NonProfits have budgets, and leadership has a responsibility to use organizational resources carefully.
But lowest price and best value aren't necessarily the same thing.
Imagine one provider costs less but requires executives to spend hours coordinating vendors, leaves recurring technology problems unresolved, or provides inadequate cybersecurity guidance. The invoice may be lower while the organization's actual cost—in employee time, leadership attention, downtime, and risk—is considerably higher.
The reverse is also true.
A more expensive provider isn't automatically better simply because it charges more.
Leadership should therefore evaluate what the organization receives for the investment and what responsibilities remain internally.
Jon Maderia, Executive Director of Martin House, addresses this point directly when describing his experience with I-M Technology. He acknowledges that I-M Technology isn't the cheapest option, but connects the investment to responsive service, protecting organizational data, security and software expertise, and the value of employees' time.
He also brings an important comparison: having worked with other IT companies, he says those experiences didn't come close.
That kind of testimony is more meaningful than an MSP simply claiming to provide “premium service.”
The question for leadership isn't:
“Who has the lowest monthly number?”
It's:
“Which provider gives our organization the strongest combination of support, risk management, expertise, and strategic value for the resources we're investing?”
What Does a Strategic IT Partnership Look Like in Practice?
The Coast Guard Foundation's experience provides a useful example.
The NonProfit supports U.S. Coast Guard members and their families nationwide. As the Foundation expanded its remote workforce, its existing technology environment was becoming increasingly difficult to rely on. It was dealing with poor Wi-Fi, aging infrastructure, unreliable servers, and limited IT support.
I-M Technology began with an assessment and developed a phased modernization plan rather than applying a one-size-fits-all solution.
The work included replacing outdated wiring and stabilizing Wi-Fi, modernizing phone systems, enabling secure remote work, gradually migrating physical servers to the cloud, and strengthening cybersecurity through layered email protection and employee training.
Importantly, existing technology wasn't automatically discarded. Older servers were allowed to reach end-of-life before moving to the cloud, helping the Foundation maximize investments it had already made.
The result was a more reliable technology environment, support for a largely remote workforce, cloud-based systems with minimal downtime, reduced cybersecurity risk, and greater efficiency for leadership.
Bradley Sisley, Senior Vice President of Development, summarized one of the most valuable outcomes particularly well. Cybersecurity remained a major organizational risk, but managing that risk required very little of his daily attention because I-M Technology was handling it.
Susan Ludwig, President of the Coast Guard Foundation, describes the relationship similarly. In her experience, I-M Technology has become a strategic partner that understands the Foundation's mission, looks for ways to improve operations and efficiency, and provides responsive support to employees both at headquarters and around the country.
That's an important distinction when choosing an MSP.
The objective isn't to find a provider that makes technology disappear from leadership conversations entirely.
It's to find one that handles the operational complexity while helping leadership focus on the technology decisions that matter.
Use These Six Factors to Compare Managed IT Providers
When your NonProfit begins evaluating MSPs, service lists will inevitably start looking similar.
That's why we recommend bringing the conversation back to six areas:
Responsiveness → Cybersecurity → NonProfit Understanding → Strategic Guidance → Transparency → Continuity
Don't evaluate these factors only during the sales presentation.
Ask for examples. Talk to references. Ask what happens when something goes wrong. Ask how recommendations are made. Ask how the provider handles a client that doesn't want to replace everything immediately. Ask how cybersecurity responsibilities are divided. Ask what leadership meetings will look like after the contract is signed.
Most importantly, pay attention to the questions the MSP asks you.
A provider can't develop an appropriate technology strategy without understanding your organization first.
If the conversation jumps immediately to products, packages, and contracts before the provider understands your programs, employees, technology environment, risks, and priorities, that's useful information in itself.
The Right MSP Should Understand the Mission Behind the Technology
For a NonProfit with 20–100 employees, choosing an MSP isn't simply an IT purchasing decision.
Technology affects employee productivity, cybersecurity, service delivery, financial planning, leadership time, and sometimes the organization's ability to serve clients at all.
The provider you choose will potentially have significant access to and responsibility for that environment.
Technical competence is therefore the starting point, not the finish line.
Look for an organization that can support employees when they need help, manage cybersecurity as an ongoing responsibility, understand NonProfit constraints, think beyond today's tickets, explain recommendations clearly, and provide continuity even when individual people change.
In other words, don't simply ask:
“Can this company manage our technology?”
Ask:
“Can we trust this company to help us make good technology decisions for our mission?”
If your NonProfit is evaluating managed IT providers, learn more about I-M Technology's Managed IT Services or schedule a Discovery Call to talk through your current environment, priorities, and the questions you should be asking before making a decision.
