10 rules for OS upgrades

It’s time to start thinking about your desktop upgrade plan before your bosses surprise you with it. It’s inevitable, so it might as well be on your terms.


Looks like Vista may actually arrive near to Microsoft's most recent release announcement: November 2006 for business editions, and January 2007 for the consumer edition. That means it’s time to start thinking about your desktop upgrade plan before your bosses surprise you with it. It’s inevitable, so it might as well be on your terms. And to make that easier, here are Oliver’s 10 Rules for OS Deployment.

1. Delay, delay, delay. Nothing screws up a desktop upgrade more than rushing in. Properly managed, time can only be your best friend. More time to plan, more time to implement, more time for Redmond to work the kinks out.

2. Harass your software vendors. Users who get new OS doodads but can’t get stable versions of what they need to get paid tend to get cranky. Call those software vendors and find out where they are with their Vista versions. That way, fewer office supplies get thrown at your head.

3. Impress the brass. Tinker with Vista and find out which new features will most impress that senior dude who signs the checks. Then do a little demo. Think shiny and small, quick movements. Keeps ’em occupied.

4. Sell your lead users. This actually requires work. Find out what’ll impress lead users in each department. That means making Vista and some third-party software do something new that will make your lead users’ lives easier -- or at the least, sexier. Or you can try mini muffins, but don’t count on it.

5. Work in a hardware upgrade. If Rule No. 4 gets too hard, combine a Vista upgrade with new desktops. The best way is to wait until your current desktop lease is up and then renew it with new machines pre-installed with Vista. It means less work for you, sexier machines and clean keyboards for users.

6. Desktops before servers. This is subjective, but I’ve always found it easier to upgrade the desktops than to roll out the back-end stuff. Fortunately for me, Microsoft is cooperating by releasing Vista before Longhorn, but if you really push Rule No. 1, you may be in a position to pick and choose.

7. Plan that data migration. A good reason for Rule No. 6: One set of data gets migrated at a time. This time it’s desktop data, so work out that backup strategy. If it’s shadow copy, make sure your users know to put their files in the right folder. This saves bloodshed on roll-out day.

8. Think small. Size does matter, especially in desktop deployments, and the ideal size here is small. I don’t just think department by department; I do it team by team. If there aren’t any teams, just create a couple.

9. Educate the public. New operating systems are scary. Microsoft even messed with Solitaire this time. You may hear sobbing. So show them what they’ll be facing -- even if it’s just the power users in each department. Your help desk will thank you.

10. Write a note. Don’t just let your users walk in one morning and face a new OS. They’re squirrelly, and you might cause a stampede. They need a global e-mail the day before and then a little note printed out on their keyboard showing them how to log in and find their key apps the morning of -- even if it’s exactly the same as under XP. Works wonders.

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