August 28, 2025
IT Issues Are Costly
Small and midsize businesses (SMBs) face a range of common IT problems that quietly drain productivity, stall growth, and expose them to cybersecurity and compliance risks. Whether you're running a law firm, retail store, construction company, or a cannabis dispensary, chances are you've already experienced a few of these firsthand.
In this guide, we break down the seven most frequent IT challenges that SMBs encounter, and how to fix them. Where relevant, we also call out additional impacts for cannabis retailers, who operate under especially strict technology and data requirements.
What Are the Most Common IT Problems for Small Businesses?
The most common IT issues that hurt small and midsize businesses (SMBs) include:
- Weak Wi-Fi or outdated networking gear, slowing operations and disrupts POS or VoIP systems
- Lack of reliable backups, putting customer and business data at risk of permanent loss
- Skipped software updates, creating security vulnerabilities and compatibility issues
- Compliance gaps, especially for regulated industries like cannabis and healthcare
- Multiple disconnected vendors, leading to delayed fixes and finger-pointing during outages
- Slow or unresponsive IT support, which drags down productivity
- No long-term IT roadmap, causing tech to become outdated, expensive, or inefficient
Addressing these issues with proactive planning, managed support, and secure infrastructure helps SMBs avoid downtime, data loss, and compliance risks.
1. Weak Wi-Fi or Network Infrastructure
The Problem:
Slow or unreliable Wi-Fi is frustrating and can derail essential business operations. Lagging internet can freeze cloud apps, kill VoIP calls, and disrupt team collaboration.
Additional Impact for Retail:
POS tablets, compliance trackers, and surveillance systems compete for bandwidth. In retail settings, poor connectivity slows checkouts and frustrates customers.
Fix It:
- Upgrade to commercial-grade routers and switches
- Use dedicated access points and network segmentation
- Isolate critical systems (POS, VoIP, security) from guest Wi-Fi
2. No Reliable Backup System
The Problem:
Without automated, secure backups, a hardware crash or ransomware attack can result in permanent data loss.
Why It Hurts SMBs:
Customer records, financial data, and internal documents are business-critical. Losing them can halt operations or trigger legal exposure.
Fix It:
- Implement cloud-based, encrypted, automated backups
- Store backups offsite and test recovery procedures regularly
- Retain version history for better ransomware recovery
3. Skipping Software Updates
The Problem:
Unpatched systems are an open invitation for malware and downtime. Yet many SMBs delay updates out of convenience or fear of breaking something.
Why It Hurts SMBs:
Unpatched apps, operating systems, and firmware increase vulnerability and reduce compatibility over time. For some businesses it can interfere with updates to systems that impact compliance reporting, especially in highly regulated industries like cannabis.
Fix It:
- Automate patching through an MSP partner
- Schedule updates during low-traffic periods to minimize disruption
4. Compliance Gaps in Your Tech Stack
The Problem:
Without secure devices, access controls, and proper documentation, SMBs risk violating industry regulations and exposing client data.
Why It Hurts SMBs:
From HIPAA to PCI-DSS to the MA Cannabis Control Commission, most industries have strict data handling requirements. Failing to comply can mean steep penalties.
Fix It:
- Use endpoint protection and full-disk encryption
- Maintain access logs and audit trails
- Train employees on secure login practices and data handling
5. Disconnected Vendors, No Accountability
The Problem:
Using multiple tech vendors without a central point of accountability means issues fall through the cracks.
Why It Hurts SMBs:
If your phone system breaks, is it your provider or your network? Without vendor coordination, downtime stretches longer and support becomes frustrating.
Fix It:
- Work with an MSP that manages third-party vendors
- Keep an internal directory of support contacts
- Standardize escalation procedures for critical systems
6. Slow or Unreliable IT Support
The Problem:
When IT issues go unresolved for hours or days, your team's productivity suffers—and so does your customer experience.
Why It Hurts SMBs:
Response times matter. A delayed fix on a downed email server, Wi-Fi outage, or password lockout slows everything down.
Fix It:
- Choose a provider with documented SLAs (service-level agreements)
- Look for live phone support and local, responsive teams
7. No IT Roadmap or Scaling Plan
The Problem:
Most businesses outgrow their tech—often without realizing it. Systems that worked fine last year may already be holding you back.
Why It Hurts SMBs:
Without scalable infrastructure and future-proof planning, IT becomes reactive, expensive, and inefficient.
Fix It:
- Conduct quarterly tech reviews
- Build a 6-12 month roadmap that includes budgets and upgrades
- Use cloud and modular systems that grow with your needs
Click Here or give us a call at 781-837-0069 to Book a FREE 15-Minute Discovery Call
Key Takeaways
- Most SMB IT issues are avoidable with proactive planning and strong support
- Poor Wi-Fi, lack of backups, and delayed updates can cost more than you think
- Cannabis retailers face additional IT pressure—but all SMBs need reliable, secure systems that scale
FAQ
Q1: What's the most serious IT risk for small businesses?
A1: Data loss and downtime—they impact both revenue and client trust.
Q2: Can any IT provider support my business?
A2: Choose one familiar with your industry's tools and compliance rules. Cannabis and healthcare businesses, for example, need niche expertise.
Q3: How often should I update systems and software?
A3: At least monthly. Use automated updates and patch management tools.
Q4: What's one upgrade with fast ROI?
A4: Network improvements. Segmented, high-speed Wi-Fi cuts downtime and improves system performance.
