IT Expert Voice

It’s been a while since the last time you had to orchestrate a major desktop upgrade. You may benefit from the cautionary advice from IT veterans who survived prior changes to a new operating system.

For many IT managers, administrators, and even end-users, Windows 7 may be the first time they’ve had to face moving to a new client operating system (OS). For IT veterans with one or more operating system migrations under their belts, it may have been a while since they had this particular “learning experience.”

While the computing landscape has changed in many ways since the last time your company endured an OS upgrade – such as more browsers to support, more compliance and other regulations, SaaS, cloud computing – some underlying truths, gotchas, and watch-out-for’s remain in effect.

Here’s some “lessons learned” and cautionary advice from IT veterans who have survived prior OS migrations. If you’ve done this before, what you read may be familiar. But it’s just as likely that you’ll see something you hadn’t done on previous upgrade rounds, or you blissfully forgot about.

Go To Fresh Hardware

If you have hardware that’s relatively new, it’s tempting to reuse it. For home users and SOHOs, maybe that makes sense. But for larger businesses, the consensus says otherwise.

“Don’t do in-place upgrades onto current systems, advises Beth Cohen, president of IT consultancy Luth Computer Specialists. Cohen has supervised OS migrations since Windows NT and Novell NetWare as director of engineering for IT at BBN and as CIO/CTO at several startups. “Swap out the hardware and do a drop-in-place new system.”

However, points out Harold Mann, president of IT consultancy Mann Consulting, “If you have legacies, like how your shortcuts or task bar are organized, this approach might be unacceptable.”

Test, Pilot Before Mass Deployment

It should go without saying – though all experienced admins say it anyway – that you test any new OS on representative computers. They emphasize that businesses need to test not just the hardware configuration, but also applications, peripherals, and configurations.

“You always want to take one machine and do a test scenario, test everything you can think of to test,” says Dan Bent, an IT technologist at Benefit Administrative Systems who has been in IT since 1991, working with and upgrading OSs including MS-DOS, Windows 3, NetWare, Unix, and Linux.

“You may have unusual or legacy hardware, which requires drivers that aren’t available,” Bent points out. “If you have legacy hardware that goes back to x386 days, and needs a special driver, or older/low-market-share software, or in-house/custom applications, that’s something I’d want to test.”

“In some cases, software vendors would not say whether or not their apps worked, so you have to do your own testing and check all the options!” recalls Chris De Herrera, best known for his work with portable and mobile devices, who spent over 20 years as an IT administrator. “The common issues we ran into were software compatibility with special hardware that was specific for our business. Most hardware manufacturers were behind the times when it came to certifying their drivers and applications with the latest OS.” How much do you want to bet has changed in that regard?

To test, you need an IT inventory, points out Nick Beaugeard, managing director at Hubone, who, at a previous company, was responsible for rolling out over 1.5 million seats of Windows 95, Windows NT4, Windows 2000, and Windows XP to major companies. “Deployments without inventory are almost guaranteed to fail,” he says. Don’t trust a manual inventory, either; use an automated software tool, Beaugeard suggests.

Migrate All Systems

A phased approach? Bah! You want to end up supporting as few versions and environments as possible, says Cohen. “Have one OS, one version, don’t try to straddle this across several years.”

In a related vein, keep it simple, urges Beaugeard, “The default install is best. It tends to be the most tested, robust, and secure configuration of an operating system. This is mainly what users have at home, and their systems work without expensive IT pros, right? Aim for ‘as default as possible’ and question any and all deviations.” Equally, don’t over-engineer desktop builds, Beaugeard advises. “Multiple Registry tweaks and customizations only serve to make the operating system less stable, resulting in massive support costs.”

Plan, Schedule

“A successful OS migration is about project planning from a business perspective,” says Benefit Administrative Systems’ Bent. “Once you you’ve tested the OS and are confident it will work in your environment, it comes down to project management.” Plan appropriate downtime to complete the migration (including hardware upgrades), or schedule the time to deploy the OS onto new systems and then deploy the systems. “Success is about planning the downtime, minimizing it… and expecting some issues to arise,” Bent says.

In moving users to new computers, you want to bring over all your users’ data. Remember that users don’t always store or save to default or recommended locations. “Think about what people have on their local hard drives,” says Bent. “Here’s where enforcing local networking policies comes into place, e.g., if they have appropriately backed-up storage… backed up, and appropriately stored on the network, the migration will be smooth. But otherwise, oops, there goes that application, or some data files.”

It’s About Your Users

“Remember ‘”WIIFM’ — ‘What’s In It For Me?’” says Bob Coppedge, president of Simplex-IT LLC. “If your migration doesn’t have a clear benefit and buy-in from the people most affected, you’re in for a tough ride.”

Be prepared for some users to push back, says Jason McKinney, a system/network administrator and IT manager for over 15 years. “People will resist it, because it’s change. For every person who’s an early adopter who can’t wait for the new stuff to come out, you’ll have three who liked it the way it was, including liking to complain about how it was.”

User discomfort may come from what seems like minor, inconsequential petty differences, like the way the Task Bar changes. “I once had an major executive get upset because the beep sound changed,” recalls Mann Consulting’s Mann.

Prepare your users for change, says IT architect and former system administrator Ernest Lilley. That means you must have a sense of what will change for them. He asks, “How radically different will an OS migration – or any upgrade – make user workflow? What will the human cost of changes be?” For example, the switchover to Office 2007 was a nightmare, because the feel of the software changed, he points out. “You need to figure out how to let users know, and what the costs are… and be ready to rescue them when they have problems.”

The Right Tools Help

“Don’t underestimate the power of sneakernet,” says McKinney. “Remote tools are the bee’s knees and can be critical for getting deployment done with reduced staffing, but sometimes you have to go there. It could be wiring, hardware – you have to see what they’re seeing.”

“Always use automation,” says Hubone’s Beaugeard, who believes that manual installs are usually a bad idea. Many tools assist with the process, including free solutions from Microsoft. However, Beaugeard cautions, “Automated tools come at risk, however; I have heard stories of an Australian government agency who rolled a wipe-and-load upgrade of Windows 2000 to Windows XP to all machines by accident.”

Things Will Go Wrong

“Have redundancy and failsafe scenarios,” says Bent. “This is where your best practices, and adherence to them, pay off. If mission critical data and apps are on the network, then if you lose a workstation for a while, at least you aren’t losing stuff.”

“Accept that no migration goes perfectly; you’re likely to lose some bookmarks, settings, et cetera,” says Lilley. “The potential data loss is my primary concern in this whole thing.”

“Don’t forget the ’soft’ stuff,” reminds Simplex-IT’s Coppedge. “Draft champions early. Take no credit, take all blame. And feed people generously during the process.”

And the best thing any savvy IT manager can do is be patient, suggests Frank Koehl, founder of Fwd:Vault. “Most IT managers should wait three to six months before rolling out a new OS to allow the market to sort out the most egregious issues, though I’ve known managers who would wait six months to a year in order to ensure hardware and software vendors are in sync with the new OS.”

“Migrating to a new operating system can be as easy as installing a new application or it can be difficult and time consuming,” says Andy Hackett, vice president of sales for TeamLogicIT. “Whether it is the former or the latter really depends on a number of factors,” summarizes Hackett. “One, does Microsoft provide a direct upgrade path from the current OS to the new OS? Two, are the customer’s applications supported by the new OS? Three, does the customer’s hardware support the new OS? And four, does the customer want to migrate their entire environment (programs, settings, favorites, data, etc.) to the new OS?”

Want more like this? Sign up for the weekly IT Expert Voice newsletter so you don’t miss a thing!