The Tao of Being A Technology Executive

The greatest challenge you face as a technology manager in a large enterprise is that most of what you do is damn invisible. It’s like a lot of house repairs: You fix the plumbing, you do the foundation, you spend $100,000—and everything looks the same.

IT management is a lot like that; half the time, nobody knows you’ve done anything. The simple fact that you kept it all working, from a technical perspective, is a miracle. It’s like, Holy Toledo!—we made it through another day and nothing happened.

To be a great technology manager, I believe you have to have done it at some level. Otherwise, you have no way of distinguishing what’s hard from what’s easy. That’s the rub—the things you know should be easy are hard, and things that seem hard, turn out to be really easy. If you can’t make those judgments, you’re not going to have the respect of the people who work for you.

Ray Ozzie is the best technology manager I’ve ever known. Ray was at Iris, working on Notes when I met him, and I was at Price Waterhouse as director of information and technology. Ray was incredibly inspirational and deeply technical—he was up in the stratosphere. But he wasn’t just a brilliant technical guy; he was someone who could aggregate and motivate and build teams of people. Very few people can balance that.

Being able to inspire isn’t important just for people who run high-tech startups, like Groove (where Ray is now), or CenterBeam, where I work. It’s something every CIO has to do. You have to shape what your people are doing as a breakthrough, even if it’s actually dull as dishwater. Because that’s an inherent desire of all technical people: They want to participate. But not everyone can be the lead architect of Windows XP.

I got some of my best advice about managing from a college adviser I had, the famous computer scientist Edward L. Glaser. It was 1968, and I had just started a programming company with my roommate. My adviser, Mr. Glaser, said, “Just assume that other people aren’t as smart as you—take that as a given. You still can’t accomplish anything big on your own—the only way you can do anything big is through the work of others.” Of course, only a fool goes through life believing he is the smartest guy around. But Mr. Glaser knew the conceits of youth—he knew how to talk to a 17-year-old.

Even with that advice, my worst mistakes have all come from thinking I knew it all.

I was running technology at a little company called the Consumer Financial Institute in Boston when the first IBM PC came out in 1981. We had an IBM mainframe and a Unix machine—which I thought was the greatest thing. I was convinced the PC would never be anything more than a game machine—that the technological purity of Unix would win out. Because of that, we didn’t embrace the PC for far too long.

My other big miss came in the early days of the Web. I was the CTO of a startup Internet company, and to save costs at a conference, we decided to share the platform with some other company. So this kid gets up and starts talking about his idea. He has this company that lets you do garage sales on the Web. And I’m absolutely mortified. I can’t believe I’ve got to get up on the stage after him. It’s an embarrassment to have to share the stage with some guy doing garage sales.

Of course, that kid was Pierre Omidyar, the founder of eBay and now a billionaire. And there it is. It happens to you over and over in life.