10 CIOs: Career Decisions I'd Do Over

"Many corporations are still managing people as if we were living in another era," says Slim. That's not a surprise for those of us who are survivors of the corporate wars. For the record, I have worked in midsized and large government and private sector organizations, and let me assure you that the dysfunctions are very, very much the same. There's always someone who has a bright idea about how to "increase productivity" by putting their thumb on people and treating people like factory workers in the industrial revolution. And, as much as your organization might "rah, rah, rah" behind the bottom line over all else, the great likelihood is that this is NOT the highest life priority for most people at your organization.

During WDS it was apparent to me that not much has changed and, in fact, that some of the bully bosses out there think that they're doing the right thing. One attendee who works in the telecommunications industry told me how her boss recently handed down an imperial mandate that employees would no longer be able to listen to music on a headset while they work. "It makes you less approachable," was the justification. Yeah, it also makes you not want to come to work if you're an introvert that needs to focus in a cubicle environment while lots of chatter is going on. The stories go on and on. Well meaning, yet stupid rule, meet worker-made-uncomfortable-and-unwelcome.

One of my favorite people that I met at the conference happened to be a lawyer. We got into a conversation about law, since I work for government in one of my roles, and she quite seriously told me that the thing that drives her crazy is that the law is this massive and powerful instrument that gets misused. For example, it's the only way, she said, for you to put someone to death legally. It completely drives her nuts that it gets used for trivia, over-regulation, and so on. This is no less true of rules and restrictions in our organizations. Rules are powerful tools. We should use them only when it is critical to do so. As one of my mentors has said to me about performance reviews, when you give a review, it's as if you're holding a megaphone to an employee's ear. Be minimal and soft.

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I am of course not advocating for a country club attitude. As I've pointed out in the past, that's a good way for the organization to burn down around your ears. But why, oh why, do we persist in doing things like asking people to "get approvals" to take some time off to go see their kid in a show? Why isn't the real position, "get the work done, and of course we're going to be flexible"?

As authors like Dan Pink have repeatedly pointed out in books like "Drive", our best and brightest don't just work for money. They do it for autonomy, mastery, and purposeful work. I would also add that the money that they do collect is for their LIFE purpose, what I call their "core." For some people, that's their dog. For others, it's their kids. For yet others, it's travel. We get in the way of that with capricious rules at our peril.

Ringleader Chris Guillebeau ended the conference with a bang. He distributed $100,000--in CASH--to the attendees there, with a mission. Go forth and contribute to something that matters. "Make an investment to a startup project. Invest in someone else because of community, adventure, and service," he said. Being part of something that matters is the reason why micro-finance sites like Kiva succeed. It's why Kickstarter projects succeed. And it's why, unless large organizations are very, very careful, they will lose their best and brightest as the micropreneur phenomenon takes hold, and as their best and brightest flee the organizations. It's still early on. Start doing something about it. Now.

Jonathan Feldman is a contributing editor for InformationWeek and director of IT services for a rapidly growing city in North Carolina. Write to him at [email protected] or at @_jfeldman.

At this year's InformationWeek 500 Conference, C-level execs will gather to discuss how they're rewriting the old IT rulebook and accelerating business execution. At the St. Regis Monarch Beach, Dana Point, Calif., Sept. 9-11.