Choosing an IT company can feel a little strange.
You are trusting another business with access to nearly everything that keeps your company running. Your computers. Your network. Your email. Your files. Your backups. Your cybersecurity. In many cases, they may even have administrative access to some of the most sensitive systems in your organization.
Yet a lot of businesses choose an IT provider after a couple of meetings and a proposal that mostly talks about computers, support hours, cybersecurity tools, and a monthly price.
Those things matter.
But they do not tell you much about what it will actually be like to work with that company six months from now.
The better question is not simply, “What IT services do you provide?”
It is “How do you actually manage our technology once we become a customer?”
If you are comparing managed IT service providers, here are some of the questions worth asking before you sign anything.
1. What exactly is included in our monthly IT agreement?
Start with the obvious one because this is where a lot of confusion begins.
When an IT company says it provides “managed IT services,” that can mean very different things depending on the provider.
One company may include unlimited remote support but charge separately anytime someone needs to visit your office. Another may include cybersecurity but only provide basic antivirus. Projects, new computers, employee onboarding, after hours support, backups, Microsoft 365 management, and network changes may all be treated differently.
Ask the provider to explain exactly what is included and, just as importantly, what is not included.
You should understand things like:
- Is day to day technical support included?
- Are onsite visits included?
- Is after hours support available?
- Is cybersecurity included or billed separately?
- Are backups included?
- Is Microsoft 365 management included?
- Does onboarding a new employee cost extra?
- Are larger IT projects included?
- Is strategic IT planning part of the relationship?
- Will we pay additional fees when something unexpected happens?
The goal is not necessarily to find the company that includes absolutely everything.
The goal is to understand what you are buying.
At Digital Boardwalk, our Fully Managed IT Services are designed to provide businesses with an entire team responsible for technical support, proactive technology management, cybersecurity, planning, and the ongoing processes required to keep an IT environment healthy.
2. How quickly will you actually respond when we have an IT problem?
Almost every IT company is going to tell you they provide fast support.
Ask them to define “fast.”
There is also an important difference between response time and resolution time.
Imagine submitting a support request because your accounting department cannot access a critical application.
Five minutes later you receive an email saying:
“We received your request and someone will be with you shortly.”
Technically, the IT company responded in five minutes.
That does not mean anyone has started fixing the problem.
Ask potential providers about their average resolution time, how they prioritize urgent issues, what happens when an issue needs to be escalated, and how customers can see the status of their requests.
Digital Boardwalk currently supports more than 20,000 monthly active users and handles more than 500,000 service requests per year while maintaining an average resolution time of approximately one hour.
That scale matters because support is not just about having talented technicians. It requires processes, staffing, escalation procedures, documentation, and accountability.
3. Who will actually support our employees?
This question gets overlooked all the time.
You meet with a great salesperson. Maybe an owner joins the meeting. Everyone seems knowledgeable and you feel comfortable with the company.
Then you sign the agreement.
Who does Susan in accounting talk to when Outlook stops working Tuesday morning?
Ask how the support team is structured.
Are you calling a giant help desk where you get someone different every time? Will technicians become familiar with your business? Are there different levels of engineers? What happens when the first technician cannot solve the problem?
Digital Boardwalk uses dedicated support pods consisting of Technical Account Managers and Senior Technical Account Managers who become familiar with a customer’s technology and business processes. Customers also have access to specialized teams covering areas such as cybersecurity, compliance, change management, cloud technologies, and other technical disciplines.
The person answering the phone matters.
The team standing behind that person matters even more.
4. What are you doing when none of our employees are asking for help?
This might be one of the most important questions on the entire list.
If you only hear from your IT company when something breaks, what exactly are they doing the rest of the month?
Good managed IT should involve a lot more than answering support tickets.
Your provider should be maintaining systems, reviewing security, installing patches, testing backups, reviewing administrative access, monitoring changes, planning equipment replacements, identifying risks, documenting your environment, and looking for opportunities to improve things before they become problems.
We actually wrote an entire article about What You Should Expect From Your IT Company Every Month because this is one of the biggest differences between reactive IT support and mature IT management.
At Digital Boardwalk, our approach includes more than 800 formally documented procedures along with scheduled monthly, quarterly, and annual quality and compliance audits.
Technology changes constantly.
The process used to manage it should not depend on someone remembering what they were supposed to check that month.
5. How are you protecting our business from cyberattacks?
“We install antivirus” is not a cybersecurity strategy.
Modern business cybersecurity requires multiple layers because there is no single product that can protect an organization from every threat.
Ask a potential IT provider exactly what its cybersecurity program includes.
You may want to ask about:
- Email threat protection
- Multi factor authentication
- Endpoint security
- Ransomware protection
- Security awareness training
- Patch management
- Password management
- Attack surface monitoring
- Security event monitoring
- Penetration testing
- Data encryption
- Cyber insurance requirements
Digital Boardwalk’s Managed Cybersecurity Services use multiple layers of protection covering users, computers, email, cloud services, identity, networks, and other parts of the technology environment.
This is important because cybersecurity is no longer something sitting quietly in the background of IT.
It affects insurance. It affects compliance. It affects your employees. It affects your customers.
And when something goes wrong, it can affect whether your business is able to operate tomorrow morning.
6. How do you know our backups actually work?
“We have backups.”
Great.
When was the last time someone tested them?
There is a big difference between a backup system reporting that a backup completed successfully and knowing that your business can actually recover from it.
Ask your potential IT provider:
- How often are backups reviewed?
- How often are backups tested?
- Does a real person verify them?
- Where is our data stored?
- What happens if our physical location is destroyed?
- What happens if ransomware encrypts our systems?
- How quickly could we restore operations?
- Who is responsible for the recovery process?
Backups should not exist just so someone can check a box saying they exist.
They exist because someday you might need them.
That is why backup verification and recovery planning are built into Digital Boardwalk’s Managed IT Services and ongoing technology management processes.
7. How will you help us plan for replacing computers, servers, and other technology?
Nobody enjoys hearing that it is time to spend money on technology.
Especially when the old equipment still technically works.
The problem is that “still turns on” and “still appropriate for the business” are not the same thing.
Older technology can become slower, less reliable, unsupported, harder to secure, and increasingly expensive to maintain.
A mature IT provider should help you see those expenses coming.
Ask whether the provider maintains an inventory of your technology and tracks the age, warranty status, operating system, security status, and expected replacement timeline of your equipment.
Your IT budget should not feel like a series of surprises.
We talked about this in more detail in our article about Why Your IT Company Keeps Recommending Replacements.
Digital Boardwalk also provides Technology Procurement Services to help businesses evaluate, purchase, configure, and deploy new technology when those replacements are needed.
8. What happens when one of our employees leaves?
This sounds simple until you think about how many places one employee might have access to.
- Microsoft 365.
- Email.
- Cloud applications.
- Shared files.
- VPN access.
- Passwords.
- Company computers.
- Financial systems.
- Customer information.
- Industry specific software.
- Maybe even physical access to the building.
Ask your potential IT company what their employee separation process looks like.
There should be a repeatable process for disabling accounts, terminating active sessions, recovering equipment, protecting company data, transferring files, removing access, and documenting what was completed.
The same thing applies when someone joins the company.
Digital Boardwalk builds repeatable employee onboarding and separation processes into its Managed IT Services so these important steps do not rely on someone remembering everything that needs to happen.
9. Will you help us plan our IT budget or just tell us when something needs to be purchased?
There is a major difference between fixing technology and managing technology.
Your IT provider should understand where your business is going.
- Are you hiring twenty employees next year?
- Opening another location?
- Moving offices?
- Changing software?
- Working toward a compliance requirement?
- Trying to reduce operating expenses?
- Moving more systems into the cloud?
Those conversations should influence your technology strategy.
A good managed service provider should help you understand what is coming so you can budget for it rather than receiving a surprise recommendation for thousands of dollars of equipment that nobody planned for.
Technology should support the business plan.
It should not constantly interrupt it.
10. What happens if we already have an internal IT person?
Hiring a managed service provider does not necessarily mean replacing your internal IT team.
Sometimes the better answer is giving that person more help.
An internal IT professional may know your business extremely well but still struggle to cover support, cybersecurity, cloud infrastructure, projects, compliance, vacations, after hours emergencies, and every specialized technology your organization uses.
That is where Co Managed IT Services can make sense.
Instead of replacing internal IT, the managed service provider works alongside them.
Your internal team can continue focusing on the areas where they provide the most value while gaining access to additional engineers, specialized expertise, cybersecurity resources, management platforms, and additional coverage when needed.
So if you already have an IT person, ask potential providers a different question:
“How will you make our existing IT team better?”
11. How do you handle compliance and cyber insurance requirements?
Even if your business does not operate in a heavily regulated industry, this question is becoming increasingly important.
Cyber insurance providers are asking more detailed questions about security controls. Customers are sending security questionnaires. Government contracts can introduce additional requirements. Industries handling financial, healthcare, government, or other sensitive information may have even more obligations.
Ask whether your IT provider understands the requirements affecting your organization.
Digital Boardwalk provides Managed Compliance Services for organizations working with frameworks and requirements including CMMC, HIPAA, PCI, SOX, ISO, and others.
We also help businesses meet technical requirements associated with Cyber Liability Insurance.
Your IT company does not need to be your lawyer or insurance agent.
They should, however, understand how the technology they manage affects your compliance and risk.
12. What happens if we decide to leave?
Nobody likes asking this during the sales process.
Ask it anyway.
You should understand who owns your accounts, domains, documentation, licenses, passwords, hardware, backups, and data.
You should also understand what the transition process looks like if you eventually move to another provider.
A healthy IT partnership should not depend on making it painful for you to leave.
Your technology belongs to your business.
Your provider should be helping you manage it, not holding it hostage.
13. How do you measure whether our IT environment is actually improving?
This question can tell you a lot about how mature an IT provider really is.
If you work with the same IT company for three years, your technology environment should be better than it was when you started.
More secure.
Better documented.
More standardized.
More reliable.
Easier to manage.
Better aligned with your business.
Ask the provider how they measure that improvement.
Digital Boardwalk takes a process driven approach to technology management focused on continuous improvement. Our team routinely audits the systems we manage, reviews security and operational processes, and helps customers plan for future technology changes.
That approach has also earned industry recognition. Digital Boardwalk was ranked #48 on the 2026 MSP 501, placing us among the Top 50 managed service providers worldwide.
Awards are great.
But the more important question is what the provider is doing every month to earn your business again.
So, what should you look for when choosing a managed IT service provider?
Do not choose an IT company based entirely on who has the nicest proposal, the longest list of software tools, or the lowest monthly price.
Look at how they operate.
Ask about their people.
Ask about their processes.
Ask what happens when things go wrong.
More importantly, ask what they are doing to prevent those things from going wrong in the first place.
You want to know:
- Who is responsible for your technology?
- How quickly problems actually get resolved?
- How your systems are maintained?
- How your backups are tested?
- How your cybersecurity is managed?
- How technology replacements are planned?
- How your IT budget is developed?
- How your employees are protected?
- How your business will recover from an emergency?
- How your technology will improve over time?
The answers will usually tell you far more about an IT company than the proposal sitting in front of you.
What if I am comparing IT companies right now?
Then ask these questions.
Seriously.
Even if Digital Boardwalk is one of the companies you are considering, ask us too.
We believe businesses should understand exactly what they are paying for and what is happening behind the scenes to keep their technology reliable, secure, and ready for whatever comes next.
You can learn more about our Fully Managed IT Services, explore our Cybersecurity Services, or see how we work alongside existing technology teams with Co Managed IT Services.
And if you are currently comparing providers and just want to talk through what your business actually needs, contact the Digital Boardwalk team.
Bring your questions.
We think your IT company should be able to answer them.