For many owner-managed SMEs, IT is something that has simply evolved rather than been strategically designed. What often began as a single server or a handful of laptops has gradually grown into a complex mix of cloud platforms, remote access tools, security systems, and hardware. In this environment, the ability to ask the right IT questions has become just as important as the technology itself.
As we move into 2026, security threats are more sophisticated, regulatory compliance is no longer optional, and business resilience is now a core measure of success. For owner-managers, the priority isn’t mastering technical detail, but maintaining control, managing risk, and having confidence in the decisions being made. The most successful leaders understand that clarity comes not from chasing new tools, but from knowing which questions to ask, and why they matter.
These IT questions determine whether you are leading your business’s technology strategy or merely reacting to the latest fire. If IT is a “black box” you don’t touch until it breaks, you aren’t in control.
1. Do we have a documented IT roadmap for the next 12–24 months?
A roadmap is the difference between planned investment and emergency spending. It should outline hardware refresh cycles, software migrations, and security milestones. If your IT provider can’t show you a plan for 2027, you are operating reactively.
2. What standards does our IT environment work towards?
Consistency is the bedrock of security. Whether your team is in the office or working remotely, their experience and security protocols should be identical. Without documented standards, “fix-on-fail” becomes the default setting, leading to an unstable environment.
3. Who owns IT decisions, us, or the MSP?
Your Managed Service Provider (MSP) should provide the data and the options, but you must own the risk and the direction. If your MSP is making fundamental architectural changes without your informed consent, you’ve lost visibility into your own infrastructure.
4. How do we know our IT is improving year-on-year?
“Nothing broke this month” is a maintenance metric, not an improvement metric. Are support tickets trending down? Is your security posture quantifiably stronger? Real improvement is measurable through non-technical progress indicators like reduced onboarding time for new staff.
5. What is our policy on ‘Shadow AI’?
Employees are likely using free AI tools to process company data. Without a policy, your intellectual property could be leaking into public AI models.
6. Do we have a ‘Digital De-clutter’ or Data Retention policy?
Storing data forever is now a liability. It increases your attack surface for hackers and raises your cloud storage costs.
In 2026, cybersecurity is a business risk, not a technical one. With insurance premiums tied to posture and ransomware becoming more automated, these IT questions are essential for survival.
7. What is our biggest IT risk today, and has it been explained clearly?
If your IT lead cannot explain your primary vulnerability in plain English, they don’t understand it well enough. You need to know the likelihood of an event and the specific impact it would have on your cash flow and reputation.
8. Are all our devices compliant with a defined security baseline?
With hybrid work now the standard, “shadow IT” and unmanaged personal devices are major entry points for attackers. You must have an enforceable policy that ensures every device accessing company data meets a minimum security threshold.
9. What happens if a staff member clicks a malicious link tomorrow?
Human error remains the primary threat vector. A robust strategy assumes a click will happen. The question is: do you have the layered protection, such as endpoint detection and automated sandboxing, to contain the threat before it spreads?
10. Do we know our Microsoft Secure Score, and do we have a target?
The Microsoft Secure Score provides a transparent window into your security posture. It’s a vital visibility tool for owners. You don’t necessarily need a 100% score, but you do need an agreed-upon target and a plan to reach it.
11. Are we compliant with current and upcoming regulations?
Compliance is a continuous process, not a checkbox. In 2026, being able to demonstrate compliance to auditors, clients, or insurers is just as important as being compliant itself.
12. How are we defending against Deepfakes and AI-powered social engineering?
Traditional “look for the typo” phishing training is obsolete. In 2026, attackers use AI to mimic your voice or video in a WhatsApp or Teams call to authorise fraudulent payments.
13. Is our supply chain’s security being audited?
You might be secure, but if your bookkeeper or a key software vendor is breached, malicious actors will have a backdoor into your data.
Most businesses overestimate their resilience until a disaster occurs. These questions help bridge the gap between hope and certainty.
14. If our systems went down tomorrow, how long before we’re operational?
You need to define your Recovery Time Objective (RTO)—how long you can afford to be down—and your Recovery Point Objective (RPO)—how much data you can afford to lose. If these haven’t been discussed, your “backup” is just a fantasy.
15. Do we have immutable backups, and are they tested?
Standard backups can be deleted or encrypted by modern ransomware. Immutable backups cannot be changed or deleted for a set period. Furthermore, a backup that hasn’t been test-restored recently is not a backup; it’s a liability.
16. Is business continuity designed around how we work today?
A disaster recovery plan written for a 2019 office-centric world is useless in 2026. Your plan must account for cloud service outages and the reality of a distributed workforce.
17. Have we tested a ‘Cloud-Outage’ scenario?
We used to worry about servers dying; now we need to worry about Microsoft 365 or AWS going offline for 12 hours. Do you have a paper-and-pen plan for when the cloud disappears?
Microsoft 365 is the engine of the modern SME, but it is often poorly governed and inefficiently licensed.
18. Do we have the right Microsoft licenses, or just the default ones?
Many businesses overspend by hundreds of euros a month by assigning top-tier licenses to staff who only need basic email. Regular license reviews ensure your spend aligns with actual usage.
19. Is Microsoft 365 configured securely, or just installed?
Out-of-the-box settings are designed for ease of use, not maximum security. If you haven’t moved beyond “default,” your sensitive data is likely more exposed than you realise.
20. Are Teams, SharePoint, and OneDrive actually governed?
Without governance, file sprawl becomes a nightmare. Who can create a Team? Who can invite guests? Proper governance prevents data leaks and actually makes it easier for staff to find the information they need.
21. Could tools like Copilot reduce admin time, and are we ready?
AI tools like Microsoft Copilot can be transformative, but they require a “clean” data house. If your internal permissions are a mess, Copilot might accidentally surface sensitive payroll info to the wrong person. Preparation matters more than speed.
22. Can we measure the actual ROI of our AI tools?
AI licenses are expensive. Are they actually saving time, or are people just using them to write longer emails that nobody reads?
23. Do we have a “Human-in-the-Loop” requirement for AI-driven actions?
As we move toward AI agents that can execute tasks, the risk of automated errors increases. You need to define which high-stakes actions still require a human “eyes-on” check before they are finalised to prevent a technical glitch from becoming a legal or financial nightmare.
24. What is our ‘IT Carbon Footprint’?
By 2026, many larger clients may require you to report your environmental impact (ESG) to stay on their tender lists. Your IT energy usage is a big part of that.
Your MSP should be a partner in growth, not just a helpdesk. These IT questions test their operational maturity.
25. What percentage of issues are fixed remotely?
High remote-resolution rates signal a standardised, well-documented environment. If engineers are constantly needing to visit your site for routine issues, it’s a sign of underlying systemic instability.
26. Do we have SLA-backed response times, and are they reported?
A Service Level Agreement (SLA) is a promise. You should receive monthly reports showing whether those promises were kept. Transparency is the only way to hold your provider accountable.
27. Do we receive regular, understandable reports?
You don’t need a 50-page PDF of technical jargon. You need a concise summary of health, risks, and progress. Reporting should provide insight, not noise.
28. When something goes wrong, who owns the problem?
When an ISP goes down or a specific software fails, does your MSP take charge, or do they tell you to call the vendor yourself? You need single-point accountability.
29. How is the MSP using AI to improve our service?
If your MSP isn’t using AI for predictive maintenance or faster ticket resolution, they are falling behind the curve, and you’re likely overpaying for “human hours” that could be automated.
30. Where exactly is our data physically stored?
With shifting data laws, knowing if your data is in Dublin, London, or the US is no longer just a technicality; it’s a legal requirement for many industries.
These final five IT questions are designed to test mindset. A proactive IT partner will have immediate, confident answers, while a reactive one will struggle.
31. If we grow from 50 to 100 staff, what changes, and what doesn’t?
Assess if they have scalable processes and standards in place, or if they just think in terms of buying more licenses.
32. If we lose a key internal admin tomorrow, are we exposed?
This tests their documentation. Your business should never be reliant on the “secret knowledge” of one person.
33. Can you show us three things you proactively improved in the last quarter?
If they can’t point to improvements they initiated without being asked, they are merely “maintaining” you.
34. If you were running our business, what would you fix first?
This reveals if they actually understand your business goals or if they are just following a technical script.
35. What should a company like ours stop doing immediately from an IT perspective?
A true partner has the confidence to challenge poor practices, even if it’s uncomfortable.
Unanswered IT questions don’t just create uncertainty; they quietly expose your business to risk, disruption, and missed opportunity. Confidence comes from clarity, and clarity comes from having the right partner beside you. That’s where Arbelos steps in.
With over 15 years of supporting Irish businesses, ISO/IEC 27001 accreditation, Microsoft Modern Work Solutions Partner status, and a proven track record of reliability, we deliver proactive managed IT services, security-first compliance, resilient business continuity, and fully optimised Microsoft 365 solutions aligned to your goals.
If you want predictable IT costs, stronger security, uninterrupted operations, and the peace of mind that comes from expert oversight, contact us today for a no-nonsense IT health assessment and turn unanswered questions into confident decisions.
As businesses continue into 2026, the gap between simply having IT and actively managing it has become a defining challenge for owner-managers. For SMEs, technology often evolves in a piecemeal way, without clear IT goals, as tools, licences, and hardware are added to...
In a competitive and fast-evolving business landscape, technology plays a defining role in success. For Irish SMEs that want to grow sustainably, protect their operations, and stay ahead of competitors, they must utilise it at every opportunity. When technology is...
Managed IT support for small businesses comes with a host of benefits that make this service essential. Aside from the cost-saving advantages associated with managed IT services, it also places SMEs in a stronger position in the context of cybersecurity and business...