What does the former CEO of HP have to tell anyone these days about how to run an IT organization? That was the question I had when I heard that Carly Fiorina was going to be in town this week, keynoting at a small conference called the Internet Telephony Expo. Given her turbulent tenure at HP, I joked with one of my colleagues that probably the best strategy for anyone at the conference was to listen to what she had to say and do the exact opposite.

And while that seemed somewhat gratuitous, after the speech I was left with a cloying feeling, like having too much MSG after a big Chinese meal. What she had to say was interesting: the nut graf, as we journos say, is that the coming digital revolution will involve transforming every piece of content and the processes that use them into portable, personal, and virtual constructs. What this means for me is a world in which we are our own IT managers, and in charge of our own digital destiny. It is a heady notion, and I for one am not sure I am ready for this level of responsibility.

At first blush, you might think this is heresy, especially coming from the guy that runs a Web site for people who do nothing but take charge of their digital domains on a daily basis. But hear me out. The job that you really have isn’t your own IT manager, but the manager for your friends and family.

Take one aspect of my digital life – my home telephone. I have been a customer of Vonage for several years, and while it hasn’t been effortless, I have enjoyed a certain freedom to never talk to a Baby Bell sales rep ever again, especially when I want to make changes to my phone features like call forwarding, voice mail and call pickup. Some of the Bells are getting this religion: last month I saw some advanced features from Verizon that allow you to make custom feature configurations via the Web like Vonage and the other IP tel providers have.

What about digital photography and music? Having all our CDs encoded on our home PC is very liberating, to be sure. I wouldn’t go back to the analog world for anything. But it has been a painful process in getting my wife on board, and it had nothing to do with technology or the bit rate the files are encoded or which music player we are using or whatever. It was all about cataloging the songs into their appropriate genres, so my wife could play blocks of music that fit her mood. You could say that as the home IT manager I forgot to do the requirements analysis, but the hard part is knowing the right questions to ask in our digital transformation.

In both cases (and I could on with other examples, but I’ll spare you), the downside is that when something goes wrong, I have to go into debug mode for my family and that isn’t a job that I relish. Particularly if I have to call the same providers that I just got freed from talking to their support reps, or spend time at night taking apart my PC.

Carly was big on transformations, which is ironic because her biggest one (in folding Compaq into HP) was far from successful. Certainly, HP has held on but has not hit any home runs then or since. Part of making transformations successful is understanding the end state of what you desire: and I think in the case of HP as well as our 100% digitally pure content world of the future, neither was a slam-dunk.

Look how much promise VoIP is, even now. While no one can argue that more businesses and individuals make use of the technology, it is far from stable and far from being universally deployed. And even in 2005, creating a single network infrastructure to operate both data and voice networks is tricky, and many IT organizations are still not up to the task of designing robust enough networks to handle both kinds of traffic.

Part of the problem is that while VoIP is a network application, it is an application that stresses networks in new and different ways that traditional IT folks don’t usually get until they are deep into the project. Second, network security takes on new levels of urgency and complexity when VoIP is running over these networks. This gets back to what I was saying about transformations.

Carly spoke about customer enablement, whereby VOIP and other disruptive digital technologies are incredibly powerful tools, helping business to compete and consumers to prosper. She mentioned how ‘this nation cannot maintain our competitive leadership without this enablement.” But I am not really sure she understands the path that we have to take to get there.

We are in the midst of a digital revolution, to be sure. But there are still many bumps along the road, and we still need better tools, too. And while “the cell phone with the camera on it has become the single most ubiquitous photography device in the world,” making use of all those digital photos and organizing them and keeping track of them is far from perfect. What we have done is created the digital equivalent of a dusty shoebox in the attic. We still need to transform the collection and display process too.