6 Questions to Ask Before Signing With a Managed IT Provider

Picking the wrong managed IT provider causes issues for your business besides just a slow helpdesk. There’s the risk of handing control of your business technology to a team that may not know your systems, cannot keep up as you grow or won’t take responsibility when something breaks.

You can’t judge a provider from its sales presentation alone either. Everyone sounds dependable during a pitch, and you don’t want to have a scenario in the future when a server fails and there’s nobody on the other end who can help.

So how do you avoid that situation? These six questions give Singapore business owners a clear way to evaludate any managed IT solutions provider before signing a contract.

1. What Are Your Documented Response and Resolution Times for Each Priority Level?

Any good provider of managed IT services should give you response times and resolution times in writing. These should cover at least three priority levels, from a minor request to a full system outage.

Response time is how quickly someone replies to your problem. Resolution time is how long it takes to fix it. Make sure both figures are included in your service level agreement (SLA), which is the contract that sets out what the provider promises to deliver.

Ensure that any verbal promises from a salesperson are put into writing. If a provider won’t put the numbers in writing, expect the same vagueness when something breaks.

Win-Pro averages a 15-minute response time during office hours, with SLA commitments documented for each priority level. Use that as a reference point when you compare providers.

2. Will Our Account Have Dedicated Engineers or a Rotating Pool?

A dedicated engineer learns your business and becomes familiar with the quirks of your systems over time. With a rotating pool, every call starts from zero and you may end up having to explain your setup all over again if something breaks.

This matters because good managed IT support depends on someone who already knows your environment. That person can spot a problem before it happens, and they can also tell you what a new application will mean for your systems.

Start by asking who will handle your account day to day, and how the managed IT provider will ensure continuity for your business if a key engineer assigned to your project leaves.

At Win-Pro, average staff tenure is over eight years, so the engineer who takes your call usually knows your systems already.

3. How Do You Handle Onboarding and Environment Documentation?

Onboarding is where the foundations of a managed IT relationship is built. A good onboarding and documentation process records your infrastructure and maps how your systems depend on each other. Say your email system relies on one particular server. The provider should know that before the server goes down, not after.

That’s why this is a good question to ask so you can find out if the provider is organised with proper processes in place to learn a new client’s systems. Providers without a process usually learn your setup the hard way, one incident at a time. You pay for that learning in downtime. Ask to see the onboarding checklist. If one doesn’t exist, treat that as a warning sign.

4. What Does Your Reporting Look Like and How Often Do We Receive It?

A well-run provider sends regular reports on ticket volumes, response and resolution times, repeat problems and security alerts. These reports show whether the provider is keeping its promises, and you shouldn’t have to ask for them.

If you only get figures when you chase for them, the results may be weaker than you have been told. Reports should arrive on a set schedule, whether the month went well or badly.

Ask for a sample report from an existing client and look at how detailed it is. Does it measure results against the service level agreement, or does it only list activity? A report that tracks performance against the SLA is far more useful than a generic monthly summary.

5. What Certifications Does Your Team Hold and Do They Cover the Platforms We Use?

Certifications are proof that a team has current, tested knowledge of the platforms your business runs on. For most businesses in Singapore, that means Microsoft 365, Azure and Fortinet, plus security frameworks from the Cyber Security Agency of Singapore (CSA).

Check that the certifications match your technology. If you run a Microsoft environment, any firm offering managed IT solutions for it should be able to name the people on its team who are certified to run it.

Ask for the current certification list and compare it with the platforms and compliance rules your business follows, including the Personal Data Protection Act (PDPA). Raise any gaps before you sign. For reference, Win-Pro holds the CSA Cyber Essentials Mark and the CSRO Penetration Testing Service Licence.

6. What Is Your Client Retention Rate and Can We Speak to a Long-Term Client?

Client retention is the clearest sign of how a provider performs. An IT managed provider with a 95% retention rate year after year has clients who keep choosing to stay.

If possible, ask to speak with a client who has been with the provider for a few years. A long-term client can tell you what the service is like once the novelty has worn off, and how the provider handled a real problem.

Put These Questions to Win-Pro

Win-Pro has worked with more than 5,000 businesses across Singapore and the region over 32 years, with a 95% client retention rate. These six questions are ones we expect to be asked, with direct answers for each.

If you are comparing providers, speak to our team about managed IT services for business and hold us to the standard above.

For guidance on supplier security in Singapore, see the Cyber Security Agency of Singapore.

Good managed IT services come with clear response times, named contacts and regular reviews. Ask any provider how its managed IT services are priced before you compare quotes. Ask every provider to explain in writing exactly what its managed IT services cover.

If you are comparing managed IT services, put each provider’s scope of work side by side before you look at price.