CEO Checklist: How to judge your Managed Service Provider on stability, risk, and business value.

Are you asking yourself the following question: “How to know if your managed service provider is doing a good job?”.

A team trying to figure out how to know if your managed service provider is doing a good job

Are you asking yourself the following question: “How to know if your managed service provider is doing a good job?”. This article gives you a practical checklist so you can tell the difference between an managed service provider that simply keeps the lights on and one that protects the business, supports growth, and stands up to board and lender scrutiny.

If you are a CEO or COO, you probably see tickets, outages, and monthly invoices, not server logs or security dashboards. You carry the risk, the spend, and the performance responsibility, yet the information you get from your managed service provider (MSP) is often too technical or too vague to guide real decisions.

The good news is that you do not need to be a technologist to judge managed service provider performance. You need clear outcomes, simple metrics, and straight answers.

Start With the Basics: Is Your Managed Service Provider Keeping the Business Stable and Secure?

Minimalist illustration of an executive dashboard with high uptime and green status indicators, representing stable IT operations. Image created with AI.
Executive reviewing a calm, high-uptime dashboard that signals stable IT and low risk after figuring out how to know if your managed service provider is doing a good job. Image created with AI.

If the core systems are shaky, nothing else matters. Stability and security are the entry ticket for any MSP relationship.

You want a partner that quietly keeps email, core apps, and connectivity running, and that treats cyber risk like a financial risk, not a hobby project.

Are systems up, outages rare, and problems fixed quickly?

Think of uptime as “open hours” for your digital business. High uptime means people can sell, serve, and operate without IT drama.

Ask your MSP for a simple monthly or quarterly report that shows:

  • Overall uptime for key systems
  • Number of outages
  • How long each outage lasted
  • Average time to resolve issues

Long outages, frequent disruptions, or the same issue showing up again and again are clear red flags. A strong MSP will track these metrics and explain trends.

For context, many MSP performance guides treat service uptime, response times, and client satisfaction as core metrics, like in this overview of MSP performance metrics you should track. You do not need every number, but you do need a short story with data behind it.

Do you see strong cybersecurity hygiene, not just tools and slogans?

Security is where boards, lenders, and major customers are turning up the heat. They are asking about controls, not just tools.

A competent MSP should be able to confirm, in plain language, that:

  • Multi-factor authentication is on for all critical systems
  • Security patches are applied on a regular, tracked schedule
  • Backups are not only taken, but also tested
  • Alerts from security tools are reviewed and acted on quickly

Ask them to show how long it usually takes to detect and contain an incident, in hours or days, not technical jargon. Then ask what has improved in the last 6 to 12 months.

If they cannot point to tangible security upgrades, or they talk only about brand names of tools, your cyber risk is likely higher than you think.

Are support requests handled fast, friendly, and with fewer repeat tickets?

Your people feel MSP performance through the help desk. If staff avoid calling because it is slow or painful, you already have a problem.

Look for three simple signals:

  • How quickly someone responds when a ticket is opened
  • How long it takes to actually fix the issue
  • How often the problem comes back

Many MSP KPI lists, like this breakdown of service desk and ticket KPIs for MSPs, focus on response time and “first-contact resolution.” You can ask for exactly those numbers in non-technical terms.

If the ticket queue keeps growing, or your team says “IT never really fixes anything,” your MSP is not keeping the basic engine of the business running smoothly.

Look Beyond IT Tickets: Is Your MSP Adding Real Business Value?

Once the basics are under control, the real question becomes: is your MSP helping the company grow, reduce risk, and free up capital? Or are they just an expensive utility?

A great MSP connects technology choices to revenue, margin, and resilience, not only uptime.

Can your MSP clearly show the value, savings, and risk reduction they deliver?

“We closed 500 tickets” is not value. It is activity.

Ask your MSP for a simple quarterly summary that ties their work to business outcomes, such as:

  • Reduction in downtime for revenue systems
  • Fewer security incidents or high-impact alerts
  • Cost savings from retiring old tools or simplifying vendors
  • Process improvements that save staff time

If you want a sense of how MSPs think about success, this overview of managed services KPIs leaders track shows how they measure recurring revenue, margins, and client retention. You can flip that thinking around and ask, “How are you improving our stability, our costs, and our risk profile?”

If they cannot connect their work to your numbers, they probably do not understand what matters to your board.

Does your MSP understand your strategy, not just your servers?

A strong MSP starts by asking about:

  • Revenue targets and growth plans
  • New products, markets, or acquisitions
  • Compliance obligations and key customer commitments

Then they align capacity, tools, and projects to that picture. That might mean sizing infrastructure ahead of a big sales push, helping you choose tools that support better customer experience, or shaping a roadmap that keeps you ready for audits.

If every conversation feels like a pitch for the next tool in their catalog, they are serving their revenue, not your strategy.

Are projects delivered on time, on budget, and without constant drama?

Projects are where MSPs either build trust or burn it.

Look at the last 3 to 5 projects they handled, such as migrations, new security tools, or major upgrades. For each one, ask:

  • Did we have a clear plan with dates and owners?
  • Did we hit the dates, or were there constant slips?
  • Did systems work as expected after go-live?

Some change is normal. Surprises every time are not. A mature MSP will share simple project plans, highlight risks in advance, and run short post-project reviews in plain language to capture lessons for next time.

A Simple Checkup: Questions to Ask If You Are Not Sure Your MSP Is Doing a Good Job

If you are still unsure, use your next MSP review meeting as a stress test. You do not need technical follow-up questions. You just need clear, direct answers that line up with the business.

Set the tone up front: you want outcomes, not jargon. Ask for short answers and a small set of supporting numbers.

Key questions for your next MSP review meeting

Use these questions as your script:

  1. How do I know if our managed service provider is doing a good job, in your words, and what data supports that?
  2. What are our current top three technology risks, and what are you doing about each one in the next 90 days?
  3. How has our uptime and incident volume changed over the past 12 months, and what caused that trend?
  4. What have you done in the last quarter to reduce our cyber risk, not just add new tools?
  5. Where are we overspending or under investing on IT and security, and what would you change first?
  6. Which projects are at risk right now, and what are you doing to get them back on track?
  7. If you were in my seat, what would you change in the next 90 days about how we work together?

You should expect simple language, clear ownership, and specific next steps. If you hear vague answers, heavy jargon, or blame shifting, take that as a signal that the MSP relationship needs serious review.

Conclusion: You Do Not Need to Speak “IT” to Judge MSP Performance

You do not need to be technical to answer the question, “How do I know if our managed service provider is doing a good job?” You need visible stability, basic security hygiene, simple metrics on uptime and tickets, and an MSP that can explain how they support growth, protect the balance sheet, and pass board scrutiny.

Your next steps can be simple: use the questions above in your next review, ask for one clear page of business-level metrics, and, if needed, bring in a neutral expert to translate technical reports into real risk and ROI.

If you want an experienced partner on your side of the table, explore how you can work with a neutral fractional CTO and CISO through CTO Input to get real control over technology, risk, and vendors. Then deepen your thinking by exploring related insights on the CTO Input blog, and turn your MSP relationship into a genuine asset for where your business is going.

Search Leadership Insights

Type a keyword or question to scan our library of CEO-level articles and guides so you can movefaster on your next technology or security decision.

Request Personalized Insights

Share with us the decision, risk, or growth challenge you are facing, and we will use it to shape upcoming articles and, where possible, point you to existing resources that speak directly to your situation.