Most business owners don’t want to become IT experts.

And they shouldn’t have to.

You hired an IT provider so someone else could worry about your computers, network, cybersecurity, backups, software updates, and all the other technology that helps keep your business running.

But there is an important difference between not needing to understand the technical details and having no idea what’s actually being done.

As a business owner or leader, you should have a general understanding of how your technology is being managed, what your IT provider is responsible for, where they see risks, and what they think you should be planning for next.

You don’t need technical answers.

You need clear answers.

Here are some of the conversations every business should be having with its IT provider.

1. How Are You Managing and Protecting Our Network?

You probably don’t need to know the model number of your firewall, how your switches are configured, or what every setting on your wireless network means.

But you should know that someone is actively taking responsibility for your network.

A good conversation with your IT provider might begin with:

“Can you give me an overview of how our network is being managed and protected?”

Your provider should be able to explain, in plain language, how they are looking after your internet connection, firewall, Wi-Fi, and other important parts of your network.

You might also ask:

• Are you actively monitoring our network?
• How do you know when something isn’t working properly?
• Are you keeping the important equipment updated?
• Is there anything in our network that concerns you today?
• Is any of our equipment getting old enough that we should plan to replace it?
• If something important fails, what happens next?

You aren’t looking for a technical lesson.

You’re looking for confidence that someone knows what you have, is maintaining it, and is paying attention.

2. What Happens When We Hire or Lose an Employee?

Employee onboarding and offboarding may sound like simple IT tasks, but they touch a surprising number of systems.

When someone joins your company, they may need a computer, email account, access to files, cloud applications, shared folders, security tools, and other company resources.

When someone leaves, that access needs to be removed quickly and consistently.

Ask your provider:

“What does our employee onboarding and offboarding process look like?”

You should feel confident that there is a repeatable process rather than someone simply remembering what needs to happen every time.

Other useful questions include:

• What information do you need from us when we hire someone?
• How far in advance should we notify you?
• How do you make sure a former employee no longer has access?
• Who is responsible for collecting or securing company devices?
• Are there parts of the process our internal team is responsible for?

This is less about understanding technology and more about making sure responsibilities are clear.

3. How Are Our Computers and Devices Being Looked After?

Your employees depend on their computers every day, and those devices have access to some of your company’s most important information.

You don’t need to understand every piece of software your MSP uses to manage those computers.

Instead, ask:

“How do you know whether our computers are healthy, secure, and up to date?”

You might follow that with:

• Are all of our company computers being managed?
• How do you know when a computer needs attention?
• Are software and operating system updates being managed?
• Are there older devices we should be planning to replace?
• What happens if a company computer is lost or stolen?
• How do you protect company information when an employee leaves?

For businesses that use Apple computers, iPhones, and iPads, centralized device management becomes especially important as the company grows.

At Digital Guidance, we use Addigy to help centrally manage Apple devices.

But as a business owner, you don’t need to understand how Addigy works behind the scenes.

The more important question is:

“Do you have a reliable way to see and manage our company devices, and will you know when something needs attention?”

If Apple is an important part of your organization, you can also learn more about Digital Guidance’s Apple technical services for small businesses.

4. What Are We Doing About Cybersecurity?

Cybersecurity is one of those subjects that can become technical very quickly.

But the business-level conversation doesn’t have to be complicated.

Start with:

“How are we protecting the company, and where do you think we’re most at risk?”

Your IT provider should be able to answer that question without burying you in acronyms or product names.

They may talk about protecting computers, securing email, using multi-factor authentication, managing passwords, monitoring for threats, training employees, or protecting your network.

What matters is that you understand the overall strategy.

You can also ask:

• What are the biggest cybersecurity risks you see for our business?
• What are we currently doing to reduce those risks?
• Is somebody actively watching for threats?
• Are there security recommendations you’ve made that we haven’t acted on yet?
• How are employees being protected from phishing and other common attacks?
• If we experienced a cyberattack tomorrow, who would respond?

That last question is particularly important.

Installing cybersecurity software is only part of protecting a business.

You should also understand who is paying attention when that software detects something.

At Digital Guidance, one of the platforms we use as part of our cybersecurity approach is Huntress, which provides managed cybersecurity and threat monitoring.

Again, the product itself isn’t the most important part of the conversation.

The business-level question is:

“Who is watching our environment, and what happens when a real threat is detected?”

For an independent perspective on cybersecurity, the U.S. Cybersecurity and Infrastructure Security Agency also provides cybersecurity guidance specifically for small and medium-sized businesses.

5. Are We Properly Backed Up — Including Our Cloud Data?

Almost every business owner has heard someone say:

“We’re backed up.”

But that’s where the conversation should start, not end.

A better question is:

“If we lost important business information tomorrow, what could we recover?”

Then go one step further:

“Exactly what are we backing up?”

For most modern businesses, there are actually two separate backup conversations that need to happen.

Are Our Computers Backed Up?

Your employees may still have important company information stored locally on their Macs or PCs.

Ask your provider:

• Are our company computers being backed up?
• How do you know those backups are working?
• What happens if a computer fails?
• What happens if a laptop is lost or damaged?
• How would we recover an important file that was accidentally deleted?

At Digital Guidance, one of the solutions we use for computer backup is Backblaze cloud backup.

But backing up your computers is only part of the conversation.

Are We Backing Up Microsoft 365 or Google Workspace?

This is one of the most important backup questions many businesses never think to ask.

Over the last several years, more and more business information has moved away from servers sitting in an office and into cloud services such as Microsoft 365 and Google Workspace.

Your email may be in the cloud.

Your files may be in OneDrive, SharePoint, Teams, or Google Drive.

Your calendars, contacts, shared documents, and other important business information may all live inside these services.

That leads to an important question for your IT provider:

“Are we separately backing up the information stored in Microsoft 365 or Google Workspace?”

Don’t simply assume that because information is stored in the cloud, your entire backup and recovery strategy is automatically taken care of.

Ask:

• Are our Microsoft 365 or Google Workspace accounts being backed up?
• Does that include our email?
• Does it include files and shared company data?
• What happens if an employee accidentally deletes something important?
• What happens if an account is compromised?
• Can we recover something that was deleted weeks or months ago?
• Who is responsible for making sure those backups are working?

At Digital Guidance, we use Dropsuite to provide additional backup protection for cloud platforms such as Microsoft 365 and Google Workspace.

Once again, you don’t need to become an expert on backup software.

The question that matters is:

“If something disappears—from a computer, Microsoft 365, or Google Workspace—do we have another copy, and can you get it back?”

That’s an answer every business owner should be comfortable with.

6. What Are You Monitoring for Us?

One of the major differences between reactive IT support and managed IT services is that your provider should be watching important parts of your technology environment rather than simply waiting for an employee to call when something breaks.

Ask:

“What are you monitoring for us, and what happens when you find a problem?”

That might include your computers, network, internet connection, backup systems, security tools, or other critical technology.

More importantly, you should understand what happens when your provider sees something wrong.

• Does someone receive an alert?
• Does someone investigate it?
• Will we be contacted if there is a serious issue?
• Are recurring problems being investigated rather than repeatedly patched?
• Are there reports or trends that we should be discussing?

You don’t need to see every alert.

But you should know someone is watching.

7. Do We Have Good Documentation of Our Technology?

Businesses change.

Employees leave. IT technicians change. Vendors come and go.

Your business should not depend entirely on one person’s memory of how everything works.

Ask your IT provider:

“If someone new had to understand our technology environment tomorrow, would it be well documented?”

You don’t need to review every page of documentation yourself.

You simply want to know that important information about your technology, vendors, systems, accounts, network, and procedures is being securely maintained.

Documentation is especially important during emergencies.

It’s also important if the person who normally supports your company is unavailable—or if you ever need to transition to another IT provider.

8. What Should We Be Planning For?

Good IT support shouldn’t only focus on today’s problems.

Your provider should also help you look ahead.

Ask:

“What should we be planning for over the next 12 to 24 months?”

That conversation might include replacing old computers, upgrading network equipment, changing software platforms, improving cybersecurity, preparing for growth, or budgeting for larger technology projects.

You might also ask:

• Is anything we use approaching the end of its useful life?
• Are there technology expenses we should expect next year?
• Are there risks we should address before they turn into problems?
• Are we making technology decisions today that could limit us as we grow?
• Is there technology that could make our employees more productive?

A good MSP should help you avoid surprises.

You shouldn’t first discover that something needs to be replaced after it stops working.

9. What Exactly Are We Paying You to Take Responsibility For?

This may sound like an obvious question, but many businesses aren’t completely sure where their IT provider’s responsibility begins and ends.

Ask:

“Can you explain what you are responsible for and what we’re responsible for?”

For example:

• Who manages employee onboarding and offboarding?
• Who works with our software vendors when there is a problem?
• Who is responsible for cybersecurity training?
• Who manages our backups?
• Who manages our network?
• What happens when a project falls outside our regular agreement?
• What happens when we need support after hours?
• Who helps coordinate technology if we open a new office?

You don’t need to memorize your managed services agreement.

But you should understand the relationship.

Confusion about responsibilities is often where frustration begins.

10. What Are You Seeing That We Aren’t?

This may be one of the most valuable questions you can ask your IT provider:

“Knowing what you know about our business, what concerns you?”

Your MSP sees things you may not.

Maybe your computers are aging.

Maybe your Wi-Fi is becoming unreliable.

Maybe there is a gap in your cybersecurity strategy.

Maybe you’re backing up your computers but not Microsoft 365 or Google Workspace.

Maybe your employee offboarding process leaves accounts active longer than it should.

Maybe there isn’t a major problem at all—but there is an opportunity to make something easier, safer, or more efficient.

You want your IT provider to bring those things to you.

You shouldn’t have to know the right technical question before your MSP tells you something deserves attention.

11. Are We Talking Often Enough?

If the only time you talk with your IT provider is when something breaks, the relationship may be more reactive than you realize.

Your business is constantly changing.

You hire employees.

People leave.

You add software.

You buy equipment.

You change workflows.

You grow.

And the risks facing your business change too.

Your IT provider should have enough communication with you to understand what is happening in your business—not just what is happening with the computers.

Ask:

“How often should we be meeting to talk about our technology and where the business is going?”

For some businesses, that may be quarterly. For others, it may be more or less frequently.

The exact schedule isn’t the important part.

What’s important is that there is an ongoing conversation.

You Shouldn’t Have to Know the Technical Questions

There is a bigger idea behind all of these questions.

You shouldn’t have to know enough about technology to manage your IT provider.

Your MSP should help you understand what matters.

A healthy conversation should sound something like:

Here’s what we’re taking care of.

Here’s what we’re seeing.

Here’s what we’re concerned about.

Here’s what we’re recommending.

Here’s what we think you should plan for next.

That’s the level of visibility a business owner needs.

You don’t need to know exactly how your firewall is configured.

You need to know that your network is being managed properly and whether there are concerns.

You don’t need to understand how backup software works.

You need to know whether your company could recover its information.

You don’t need to understand every cybersecurity product.

You need to understand the risks facing your business, what is being done about them, and who will respond if something happens.

You don’t need to understand mobile device management.

You need to know whether the computers and devices accessing your business information are actually being managed.

And you shouldn’t have to chase your IT provider to find out.

What If You’re Not Having These Conversations?

As you read through this list, you may realize that you don’t know many of the answers.

That doesn’t automatically mean you have a bad IT provider.

But it does mean it’s probably time for a conversation.

Ask them.

A good provider should welcome the opportunity to explain what they’re doing, what they’re seeing, and how they’re helping protect and support your business.

But what happens if the answers remain vague?

What if:

• Nobody seems to know exactly what is being managed?
• You only hear from your provider when something breaks?
• Cybersecurity risks aren’t being discussed?
• There doesn’t seem to be a technology plan?
• You aren’t sure what’s actually being backed up?
• You don’t know whether your Microsoft 365 or Google Workspace data is protected?
• You aren’t sure what your monthly agreement actually covers?
• You no longer have confidence that your technology is being looked after?

At that point, there may be a different question you need to ask:

“Is this still the right IT provider for our business?”

That’s not always an easy question.

Businesses often stay with an IT provider for years because changing feels complicated. Your provider may have passwords, documentation, historical knowledge, access to important systems, and relationships with your other vendors.

But history alone shouldn’t be the reason you remain in an IT relationship that no longer meets the needs of your business.

If It’s Time for a Different Conversation

We’ve created an educational guide specifically for businesses that are beginning to ask these questions.

How to Break Up With Your IT Support Provider walks through what a healthy IT relationship should look like, warning signs that the relationship may no longer be working, and what to consider before making a change.

Changing IT providers doesn’t need to begin with frustration or with a sales pitch from another IT company.

It can simply begin by understanding what your business needs, what you’re receiving today, and where the gaps may be.

Sometimes the most important step isn’t changing IT providers.

It’s simply starting the right conversation. Get In Touch