A Year-End IT Checklist for Business Owners
As we approach the end of the year, many business owners are focused on budgeting, planning, and closing out projects. But there is one area that often gets overlooked—and it could cost you more than you think: your technology infrastructure.
In Episode 83 of Stimulus Tech Talk, CEO Nathan Whittacre walks through the key areas every organization should review before the calendar flips. From eliminating unused licenses to preparing for Windows 10’s end-of-life, this checklist is essential for protecting your business, reducing costs, and planning effectively for 2026.
Below is a summary of the key insights from the episode, formatted as a practical guide for your year-end IT review.
1. Eliminate Unused Licenses and Accounts
Many businesses continue paying for user licenses they no longer need. Employees leave, vendors move on, but their accounts remain active—and billing continues.
This is not only a cost issue, but also a security concern. Old accounts can become back doors for hackers.
Action steps:
- Review all user accounts across your systems, including Microsoft 365, VPNs, and business apps
- Deactivate accounts for former employees and vendors
- Cancel licenses that are no longer in use
Regular account audits should be part of your security hygiene. Doing this now can reduce monthly costs and eliminate unnecessary risk.
2. Review Your Password and Access Practices
Weak or shared passwords remain one of the top causes of security breaches. Many small businesses still allow password reuse, fail to implement multifactor authentication (MFA), and rely on shared logins for key accounts.
One example discussed in the episode involved a compromised Facebook ad account that was still linked to a former employee’s personal login. This type of oversight can result in direct financial loss.
Action steps:
- Ensure every employee uses a unique, strong password for each system
- Use a password manager to reduce reuse and track credentials
- Enable MFA on all critical accounts, including email, banking, and business software
- Remove personal accounts from company assets such as social media platforms
These basic actions significantly reduce the chances of unauthorized access.
3. Evaluate Hardware Lifecycle and Budget for Replacements
Outdated hardware slows productivity and increases maintenance costs. Even worse, older machines may not be compatible with current software or security updates.
Nathan recommends the following lifecycle guidelines:
- Replace desktops and laptops every 3 to 5 years
- Replace servers every 5 to 7 years, depending on warranty coverage
- Review firewalls, switches, and wireless equipment for firmware updates and end-of-life status
Action steps:
- Identify hardware over 3 years old and assess performance
- Budget now for replacements needed in the next 6 to 12 months
- Take advantage of Section 179 deductions if you plan to make purchases this year
Ordering ahead of time helps avoid supply chain delays and spreads out expenses across fiscal years.
4. Addressing Windows 10 End-of-Life
As of October 14, 2025, Microsoft has officially ended support for Windows 10. This means no more free security patches, updates, or bug fixes. For businesses still using Windows 10, this creates immediate security, compliance, and performance risks.
Although Microsoft is offering Extended Security Updates (ESUs) for a fee, this is a temporary solutionand an expensive one. It also does not address compatibility issues with newer applications and services that will increasingly require Windows 11.
If you’re still running Windows 10, now is the time to act.
- Identify systems still running Windows 10.
Create an inventory of all devices and confirm operating system versions across your organization. - Determine upgrade eligibility.
Check whether existing machines can be upgraded to Windows 11. If not, they will need to be replaced. - Plan hardware replacements strategically.
Spread out costs by prioritizing critical users and older machines. Consider using remaining 2025 budgets or planning early 2026 purchases. - Avoid long-term reliance on Extended Security Updates.
If you're paying for ESUs, use that time wisely to phase out unsupported devices. These updates are a short-term stopgap—not a sustainable solution. - Coordinate with your IT provider.
Ensure that your transition plan includes data migration, software compatibility checks, and staff communication to minimize disruption.
Upgrading your systems is not just about staying current—it’s about protecting your business from security threats and ensuring ongoing support from software vendors. Acting now reduces risk, controls costs, and prepares your business for a more secure and productive future.
5. Audit Your Software Subscriptions
Software has largely shifted to a subscription-based model. While convenient, it also makes it easy to accumulate unused or duplicated services that auto-renew annually.
Many licenses are also tied to specific users, and businesses continue paying long after the user is gone.
Action steps:
- Create a software inventory, including who each license is assigned to
- Track renewal dates and billing cycles
- Cancel unused or duplicate subscriptions before renewal
Even a few redundant subscriptions can add up to thousands of dollars in annual savings.
6. Review Compliance and Cyber Insurance Requirements
Compliance frameworks like HIPAA, PCI-DSS, or CMMC are evolving. So are the expectations of cyber liability insurers. Many policies now require MFA, regular patching, and endpoint protection to remain eligible for coverage.
Action steps:
- Review your current compliance obligations for 2026
- Confirm that cyber insurance policies are still valid with your current security posture
- Make necessary adjustments before renewal periods
Working with your IT provider now ensures you are not caught off guard during an audit or claim process.
Wrapping it Up
Technology should be an advantage, not a liability. As we move into 2026, a proactive review of your systems, licenses, hardware, and security is one of the smartest investments you can make.
You do not need to know all the technical details yourself. But you do need to know that someone is helping you ask the right questions, assess risk, and plan ahead.
At Stimulus Technologies, we help businesses like yours reduce IT stress, improve reliability, and get back to doing what they do best.
Listen to Stimulus Tech Talk on your favorite podcast platform or watch on Stimulus Technologies YouTube channel.
