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Should I upgrade my business computers to Windows 11?

It’s that time again. Microsoft will be releasing a new version of Windows for personal computers and laptops in the next few months. The age old question remains, should I upgrade my business computers to Windows 11? Lets discuss some of your options:

  • Upgrade now to Windows 11
  • Upgrade later to Windows 11 (6 months to 1 year)
  • Skip Windows 11, making the assumption that Windows 12 will be released in 4-6 years
  • Move off Microsoft technology
Computers are used in offices and professional business for almost everything. Making the choice to upgrade is not a decision to take lightly.

Upgrade now to Windows 11


  • New technology, latest and greatest features. These features can improve productivity, connectivity and make the computer easier to use.
  • Windows 11 will come preinstalled in new computers – so it’s virtually free if you are replacing your computers
  • Keeping all systems at the same operating system version can help keep support costs down


  • As with all new things, bugs will be present and take time to work out. Upgrading early means more support calls, more strange PC behavior and more patches and updates.
  • New tools means employee training. Employee training means a short term loss in productivity for both computer users and systems administrators.
  • Windows 11’s new features will require hardware changes to take advantage of them all. In order to get the most out of Windows 11, and thus the latest and greatest features, you may require expensive PC upgrades.

The major advantage to upgrading now in my opinion is to take advantage of the latest and greatest features. The major disadvantage is the costs associated with doing that. So if your company has the budget, your current computers are showing their age, and you don’t mind working through growing pains with a new operating system, upgrading to Windows 11 in the short term may make sense.

Upgrade later to Windows 11


These are the same as upgrading immediately except

  • The biggest advantage over doing this right away is that bugs will be (mostly) worked out.
  • Time to train support staff and do a planned deployments over time to minimize disruptions and test hardware/software.
  • A budget for upgrades can be established.


These are the same as upgrading immediately except

  • You’ll be running two different versions of Windows. One version on your new computers and one version on all the rest.
  • Some employees will have access to the new features and some will not. This may become an a political issue within the office.
  • Software and peripheral compatibility with those that have Windows 10 and those that have Windows 11 may become a problem.

Overall, we take the approach of maximizing uptime and emphasizing productivity over deploying the latest and greatest feature set. A pragmatic approach in our opinion is best. In our opinion, upgrading to Windows 11 for people running Windows will happen in almost all cases. However in business you need to consider expenses, productivity and customer service. Taking a delayed upgrade approach is a great way to overcome the upgrade disadvantages.

Skip Windows 11 and upgrade to Windows 12


  • Status quo for now, no training or compatibility problems.
  • Lowest cost option
  • Windows 10 will be supported by Microsoft until October 2025 (as of the writing of this article).
  • Skipping upgrading until that time (4 years from now) may place your office computers into a better upgrade cycle.


  • Access to the latest and greatest features will not be available
  • New equipment will have Windows 11 preinstalled. To keep the version at Windows 10 you will have to downgrade the operating system.
  • At some point you may have to upgrade if Microsoft changes it’s operating system release cycle.

We like holding off upgrades between upgrade cycles. If your computers are reasonably current you may be able to skip Windows 11 altogether and move to the next version. This is assuming Microsoft keeps releasing Windows versions like it has done in the past.

Move off Microsoft technology


  • An opportunity to evaluate whether there is a better mousetrap. It gives your business a chance to evaluate if there is a better operating system for the job.
  • With ChromeOS, MacOS, Linux and all it’s various types, there has not been a better time to look at your options
  • Security patches and update cycles of Windows can be challenging to manage
  • Overall less data and bandwidth requirements, or at the very least more control over what data and bandwidth is used
  • Overall less telemetry collected
  • Easier for mobile workers to limit data consumption
  • Many options for hardware and software
  • Linux operates quickly on almost all equipment from the oldest PCs to the newest
  • Apple controls the operating system and hardware (best compatibility) and Apple has some really great processor technology
  • ChromeOS operates on very low cost equipment and is simple to use
  • ChromeOS is common in education. In several years it’ll become the operating system that your younger employees are most familiar with.
  • Total Cost Of Ownership for a business that has made the switch is lower than Windows and Microsoft’s ecosystem.


  • Changing from Windows can be very disruptive to your business and usually needs to be done all at once.
  • Training can be challenging
  • Employee’s may initially reject the changes
  • There may be some proprietary software that must run on Windows in your business. An evaluation will be required.

Overall we like the idea of getting off Windows and moving to a more suitable operating system IF that operating system performs all the functions you need efficiently and securely. No one says you must stay with Windows when equipment comes preinstalled. Pick the best tool for the job and run with that.


We believe that every business is different and that what works for your business has to be supported by your employees. Windows 11 is the latest operating system from Microsoft and it’s going to be the best one yet, but that doesn’t mean it’s the best tool for the job, It may or may not be.

Should I upgrade my business computers to Windows 11? Our answer is maybe. We know some folks will disagree with our opinions in this piece. This is a contentious topic and ultimately is up to you, your employees and your business requirements. We’d like to hear all your opinions on the topic, so please leave your comments below!

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