Windows 7 has been regarded as a make or break product for Microsoft, with many inside and outside IT left with a bad taste in their mouth from the company’s Vista operating system. While I have enjoyed my experience with Windows 7 thus far, we certainly do not need yet another review of the software here. In my mind, perhaps even more interesting than the new operating system are the lessons that a CIO and his or her IT shop can learn investigating Microsoft’s missteps with Vista, and attempts at redemption with Windows 7, as these apply to nearly any organizational effort, be it rolling out a new corporate application or delivering millions of copies of a new operating system.

Lesson 1: Don’t forget the core “experience”

While this may sound like consultant-speak, critical to any application is the experience of using the software. Microsoft touted Vista as having lots of improvements to the user experience, from an enhanced UI to improved ancillary applications. While all this was well and good, merely booting up Vista was a painful drawn-out experience. No matter how wonderful your interface looks, beginning your interaction with a computer with five minutes of “Please Wait” is difficult to recover from.

Regardless of what application or project you are deploying, determine the handful of key “experience” related metrics. Just as Microsoft focused on boot times with Windows 7, ensure that basic expectations of how users will interact with your system, process or application are met. While employees at your company likely have far less choice about which applications they use as compared to the average consumer, the “sale” will be a lot easier if initial impressions of the system are positive, and critical business scenarios are intuitive and easy to perform.

Lesson 2: Acknowledge your problems

Arguably it took Microsoft too long to acknowledge the problems with Vista. Many were fixed or mitigated as service packs for Vista were released, and once the release timeframe for Windows 7 was clear, Microsoft openly acknowledged Vista’s flaws, made the case for how Windows 7 would fix them, and moved forward.

Similarly, you are not going to win every battle as CIO, and will likely release an application, system or two that is a turkey. If complaints are legitimate, impact performance and usability of the system, and continue after the initial adjustment period of implementation, acknowledge and attempt to fix or mitigate them. Avoid the old platitude of “managing expectations” or using management-speak to avoid labeling anything a problem and address the problem head on, and detail how you will attack it.

Lesson 3: Let the users in early and often

While there was much hullaballoo about all the usability testing that was done with Vista, I personally encountered few people that had laid their hands on the operating system before it was released. On the contrary with Windows 7, even minimally tech-savvy people were downloading the release candidate and running it on all kinds of hardware, providing a massive testing cycle as well as free PR and buzz for the new OS. With enterprise systems, the sooner you can let “real” users get their hands on a new system the better. Not only will they provide valuable feedback and exercise the system in ways you may never have imagined, they will also keep your IT organization honest since they will provide immediate, honest and trustworthy feedback about what you are working on.

These lessons are simple to understand and conceptually quite obvious. Yet the world’s largest software company clearly forgot these caveats as it released one of its most important and visible products. This example should serve as a model for CIOs to remain vigilant and, like Microsoft, not take their dominant position in the “market” for granted. Your IT shop is no longer the only game in town, with competition ranging from old threats like outsourcing to the emerging availability of off the shelf applications in “the cloud.” Microsoft seems to have redeemed itself with Windows 7; hopefully your IT organization can learn a far less expensive lesson by contrasting the Vista and 7 releases.

Patrick Gray is the founder and president of Prevoyance Group, and author of Breakthrough IT: Supercharging Organizational Value through Technology. Prevoyance Group provides strategy consulting services to Fortune 500 and 1000 companies. Patrick can be reached at