I’ve been using Microsoft-based desktop PCs for a long time. I remember buying a light brown desktop PC in a huge metal case and having also to buy DOS 4.0 separately so it could run software. DOS 5.0 was not far behind, and I’ve been faced with operating system upgrade decisions in small businesses ever since.

The release of the Windows 8 Consumer Preview in February reminded me that yet another OS upgrade decision will soon be upon us. And although I, and many other cogs in the SMB machine, tend to wait out the initial stage (aka Service Pack 0), the fact that the world is moving on requires that we give some thought to whether we should join the bandwagon.

I look at every small business OS-upgrade choice as a cost/benefit ratio. Calculate the cost, calculate the benefit, and divide. It’s a subjective and metaphorical number, to be sure, but the process of trying to calculate it is a useful one. It forces you to evaluate the decision on the basis of facts and not just emotion. If the costs outweigh the benefits, upgrading should wait. The benefits must outweigh the costs for an OS upgrade to make sense.

Let’s take a look at the variables you should consider.

The costs

Costs come in the form of both time and money, so we’ll count both.


The first and most obvious cost is that of licenses. Microsoft has not released pricing for Windows 8, but you should count on something north of $100 per PC at a minimum, not counting the cost of staff time to do the upgrades. It’ll be higher if you’re buying full licenses instead of upgrades. When counting this up, remember to include any PCs or laptops that aren’t obvious upgrade targets at first; it’s better to count those costs and subtract them later if you find you can leave some machines out of the process than not to count them and then find yourself needing to spend money you don’t have.

Cost: $100+ per machine

Installation time

The second cost is that of installation time-the time it takes to do the upgrade on each machine, which never goes flawlessly. Whether you do this yourself or hire it out, this cost is always higher than that of the licenses. If you hire it out, remember that your staff will still be entirely unproductive during the upgrade, which means that it’s always going to cost you something. And if something goes wrong and the installer hasn’t taken adequate precautions, you could spend even more time cleaning up the mess. Figure on at least half a day for each machine, plus the out of pocket cost your consultant charges, if applicable.

Cost: One half day per person + installation T&M


The third cost hits after the upgrade is done, and that is the cost of leaving behind familiar ways of doing things. Even if you ultimately decide that Windows 8 is easier to use than Windows 7 (or XP) was, it will still change the way you and your coworkers work. And although Microsoft promises that the Windows 7 desktop will be available as an “app” in Windows 8, that’s little more than a hack that lets you get going quickly, before you really know what you’re doing. You won’t be learning how to use Windows 8’s UI as long as you’re using its Windows 7-style desktop, you’ll just be coping. Sooner or later, you’ll have to invest time in adopting Windows 8’s ways.

Trust me on this one-this cost will be high. Windows 8 is a radical departure from the habits you’ve acquired. No matter what you do about this, you and your people will lose a lot of time figuring out how to be productive on Windows 8.

Another issue on this topic is that the whole Metro UI is geared toward consumers, not workers, meaning that it’s designed to appeal to those using up their leisure time-music, videos, social media, that sort of thing. It remains to be seen how much of this new stuff will fit into your work life.

The bottom line is that everyone will have to stop doing things from force of habit; nothing you do will be efficient for a while. I would set aside at least a whole week, starting with the one in which you do the upgrades, for this. You are paying the price of finding out where everything went and how to get things done, and there will be a lot of hits and misses. Remember, Vista was less of a leap from XP than 8 is from 7.

Cost: One to two weeks per person.

Replacing software

The fourth cost comes from finding replacements for applications that won’t run on the new OS. Microsoft says that anything that runs on Windows 7 will run on Windows 8. If true, this won’t be an issue. But you would be wise to get news on the applications on which you rely before taking this assumption to the bank. Make an exhaustive list of applications and utilities that each person who will be getting an upgrade uses, and check with the vendor for all of them. And then find a way to test them on a real machine.

Cost: Several days to research application compatibility

The benefits

The benefits are much harder to pin down. Microsoft, and some reviewers, will always claim that the newer version is easier to use than the previous version, but usability is too subjective to matter. Many claimed that Vista was easier to use than XP, but I never did.

In the case of Windows 8, the usability equation is even murkier. So much new replaces so much old that little will be the same, making most of your acquired habits an enemy of your intuition. Is it easier to point to an invisible hotspot in the corner of the screen than to click on a Start button? Even if it is, is it easier when you need a touch screen and don’t have one? For the past 18 years, Microsoft preached the importance of “discoverability” in user interfaces, but no longer. Now, Microsoft is giving up discoverability like a bad relationship. Whether it’s easy to use or not, you’ll need training to learn how to use it. You won’t be able to just figure it out. So if I were you, I would not consider usability in to be a benefit. Just leave it out of the equation.

The benefits that matter are new capabilities. Typically Microsoft claims that the new OS corresponds with the dawn of a new era of something, and the new OS lets you join it. Let’s see what new stuff Windows 8 brings.

Metro-style applications

The Metro UI, a smartphone-style interface, is Windows 8’s most visible new capability and one that I think bears some attention. If you’ve ever seen a smartphone, you’ve seen the basic concept-you navigate the machine, and your applications, through a set of tiles using gestures and swipes. It looks and feels exactly like a smartphone.

It’s not the look and feel per se that may benefit you so much as the applications designed to take advantage of it. Developers will write some new applications for this way of doing things, and you’ll need Windows 8 to run them. The question is: Do you need any of them? Do you even know what they are? If the answer’s yes, add points for this benefit. In other words, if you see some new Metro-style applications on the horizon, consider the capabilities they bring as part of the equation.

Just remember that gestures and swipes are for touch screens, not mouse and keyboard users, so the benefit here depends on whether you have the hardware to take advantage of it.

So, if you need to run (or develop) Metro-style (touch-screen) applications, this capability will drive the benefit side of the equation up. If not, it simply gives you access to all the new software being written, if you have the hardware.

Benefit: New apps

Picture passwords

Windows 8 will let you create a logon password that consists of a series of gestures over an image. For example, you could view a photograph of your family, draw a circle around one person, drag a line across another, and associate that set of gestures with your account. You then use those gestures while viewing the photograph to log into Windows.

Is this really a big enough benefit to mention? I think so. For some people, remembering passwords is a huge problem, leading to unsecure desktop logins. A good business PC needs a strong password. If you can’t remember it, you have a business vulnerability. Some people will find it much easier to remember a series of gestures than an alphanumeric sequence.

Again, the downside is that you have to have a touch-screen in order to use it. So if you’re upgrading an existing, mouse-driven machine, this benefit will add zero points.

Benefit: More-secure desktops

Windows Live credentials and SkyDrive

Windows 8 lets you link a local account with a Windows Live account, an account that authenticates you in the cloud rather than locally. If you have more than one Windows 8 PC, this lets you share the same commonly-used settings across all of your machines. You get the same look and feel and common access to your Metro-style applications. If you travel a lot or use different machines in different places or just need a more predictable user experience in all of these various locations, this capability may be worth something to you. The downside is that the benefit is limited to common Windows settings and Metro-style applications only.

The bigger benefit here comes from SkyDrive. SkyDrive is a Windows Live service and web site that lets you store files in the cloud, and you can use it now with Windows 7. But with Windows 8, SkyDrive becomes a Metro-style application and an integrated part of the operating system. You can store files in SkyDrive with Explorer-like efficiency, and then get access to them from any other Windows 8 PC you log into. This makes it a lot easier to work on files from different machines and spares you from having to email yourself files or copy them to USB drives before leaving the office.

Of course, this all falls down whenever and wherever you don’t have reliable, high-speed access to the Internet. I’ve gone plenty of places where reliable, high-speed connectivity is a problem. Consider this before plunging in with both feet.

Benefit: Mobility options

Storage spaces

Windows 8’s Storage Spaces is a virtualized form of storage-a way of grouping a set of real hard drives into one large hard drive that doesn’t actually exist, so you can expand your storage and make it easier to manage. Even better, it lets you use classic data-protection schemes like mirroring and striping. Sounds like RAID, doesn’t it? That’s essentially what it is. But in this case, it’s accessible enough that it may actually be something that SMBs can use and manage without an IT specialist on board. It’s available on both server and client, and it’s relatively easy to set up.

This is one area where I think Windows 8 could be of great benefit to you. Many SMBs have a big problem with data protection, because they don’t have the money or time to manage complex data-protection schemes. It’s always been true in the companies I’ve worked for, all of which have been SMBs. (I suppose the exception might be those that are funded by venture capital, but they are a tiny minority.) Their data is just as important to them as it is to larger businesses, but the resources are just not there. Storage Spaces promises to change that.

So, if you have a lot of data that that is not adequately backed up, or if you are constantly struggling to come up with enough storage for your business, give this one big points. It’s a significant benefit.

Benefit: Data expansion and protection

Other miscellaneous, tiny little new capabilities

Windows 8 brings a lot of other new capabilities, but I don’t consider any of them very significant to SMBs. Here are some of the ones that might contribute to your decision:

Internet Explorer 10 will be available in two versions, one as a desktop-style and another as a Metro-style application. It promises to have better support for HTML5 and CSS3, and to be faster, than previous versions of IE. Other than that, it remains to be seen how much bang you’ll get for this buck. Refresh and Reset, two ways of undoing icky changes to Windows, will make it easier to back out of an installation gone bad. It’s System Restore in two different colors, the second of which essentially reinstalls Windows. I, for one, welcome this kind of change, but it’s a two-edged sword. If it has the results that users expect, it may be a boon to SMBs, who need all the push-button solutions they can get. If not, it could be like giving hand grenades to children. We’ll see. Windows To Go will let you put your Windows 8 installation on a bootable USB drive. This is not exactly a mainstream feature, but it will certainly be welcome by small development shops like mine.

Benefit: Minor improvements


I used Windows Vista for four years before switching to Windows 7. I was slow to upgrade because I couldn’t see much difference between them. But on those occasions when I did use it (usually helping someone else with a problem on their machine), I noticed that it booted significantly faster than mine-so much faster, that it caught my attention. I had noticed that my Vista machine booted slowly and found myself annoyed by it, but the slowness really came to light whenever I used a Windows 7 machine. When I finally upgraded, I could hardly believe the difference. I’ve got other reasons for having made the move, but for me, the boot time became a surprisingly significant reason to upgrade.

I bring this up not because Windows 8 promises to boot faster than Windows 7, but because there may be benefits that you can’t learn about without using the system, and the only one who can determine their value is you. So if possible, even if you decide not to upgrade, find a system that you can play with. Get some experience with it. See if you notice anything that proves to be valuable to you, something you weren’t looking for. You may find a compelling reason not listed in the features.

Benefit: Intangibles

One more thing

Having said all this about costs and benefits, remember that the specifics of your situation trump all. Your business is unique, and nothing any writer can outline in a blog will speak to the issues that only you experience in the day-to-day operations of your business.

Therefore, you need to take samples. Get some experience with it. Get at least one person to install Windows 8 and use it in some capacity in the context of your business. Give this person some time and the means to exercise it. Install and run applications that your company needs to run. And do it before you upgrade the whole company. There’s no teacher like experience, and this experience will give you someone who has sorted through the issues before everyone else has to.


Windows 8 is upon us. Should you upgrade when it’s released? Get yourself a spreadsheet and do a cost/benefit analysis. Doing this will help you size up both halves of the equation in the context of your business. Whatever you do, don’t panic. Windows 7 will be around for a long, long time; there is no need to join a bandwagon that may not be going in your direction. Nothing bad will happen if you take your time with this-if anything, it’ll help you be clear about why you’re doing it.