7 Pieces of Advice Before Upgrading

By Dale Denham

Most everyone wants the latest and greatest upgrade to technology, especially when it’s a free update, like Windows 10 or IOS 9. Even enterprise software users desire the latest upgrade.

Consumer upgrades are relatively easy, as shown by the many IOS 9 upgrades that have gone smoothly. Yes, there are real problems from a small percentage of users, but most are fine. Same with Windows 10; I have upgraded three machines, and two work great—the third works great most of the time. Same device, same upgrade, but for some reason some people have issues and others don’t.

Upgrades nearly always have some new feature that exposes a previously unknown flaw. When you are dealing with personal equipment, such as a phone, problems are usually fixed with help from your favorite “techie.”

However, enterprise software comes with a much larger set of issues when considering upgrades. The most important question you should be asking before upgrading is:

How much have we customized the software?

For every customization you make to software, the complexity of an upgrade increases. As you increase the number of customizations, the complexity rises exponentially.

If you have “off the shelf” software running in your enterprise, upgrades still aren’t a sure thing, but they are much easier. You still have to ask the most important question when it comes to upgrades:

Why do I want this upgrade?

If the answer is "to stay current," you should wait a few months and see what problems others experience. Skip at least every other major version as well if staying current is your reason. If there is a specific set of features you want, perhaps upgrade a bit sooner. However, never upgrade within the first month of new software.

Even then, you still need to determine:

What impact will this have on users?

Upgrades usually introduce a new set of options or features, which sometimes change what users have come to rely on. In some cases, there are minor changes that you discover only after the upgrade, and you wish you could go back. Contemplate what effect this upgrade will have on everyone who uses the software.

Advice:

Never install .0 upgrades (IOS 9.02 instead of IOS 9.0).
Wait one month before upgrading your consumer devices.
Be prepared to have a few problems and troubleshoot them.
Read about the benefits and drawbacks of the upgrade from other users.
Train your users (for enterprise software) weeks before the upgrade.
Provide your users (and/or yourself) hands-on time with the software before the upgrade.
Try to stay no more than two major versions behind the current version.

One final word. Most cloud-based software (Office 365) forces upgrades on you, as does Windows 10. You can usually delay the update for several weeks. You should not wait too long for Windows, as security patches are important.

As usual with IT, the real answer on whether you should upgrade is "It depends."

Should I Upgrade?

Windows 10: You are better off buying a new machine, as new hardware is being built specifically to take advantage of Windows 10 architecture. If your machine is out of warranty, you will have to pay for support if the upgrade causes problems. However, Windows 10 does seem to work on most old hardware. Ironically, my seven-year-old Dell desktops work better with Windows 10 than my three-year-old Lenovo Yoga.

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Dale Denham Author's page Dale is a business leader who is best known for providing business-focused I.T. leadership. He believes technology is not limited to increasing efficiency, but is essential to driving revenue. Dale strongly believes having great people is the critical ingredient to success no matter how great your technology might be.Known to many in the promotional products industry as a leading technologist, Dale is using his mix of business and technology to help drive the industry forward. One of the leaders and founders of the PromoStandards effort, Dale and others are working hard to address industry inefficiencies. Dale also is a board member of PPAI through 2018.Follow Dale on Twitter @daledenham or connect with him on LinkedIn via http://www.linkedin.com/in/daledenham.