7:30 AM, on Monday, December 5th, 2011, flight 1052. As I took my seat in Southwest Airlines' "Business Class," otherwise known as the exit row, I gave a nod to my new seat mate and noticed his MacBook on the tray table. He was reading something on his iPad and set it down for a second to send a text message from his iPhone. Now there's a Kool-Aid connoisseur, I thought. "Going to Salt Lake or beyond?" I asked. "Salt Lake. Gotta visit some customers, and after that I have to go to Boise to train our western region sales team."

And so the conversation began. I learned that his name is Jamie, he is in sales, travels every week, loves his job and his company, and is the top sales performer. $3M in quota last year and his secret sauce is knowing his customers' businesses better than they do, and delivering value with every interaction. He said, "Last week I had a meeting with a new prospect for the first time, and they couldn't believe I showed up without slides, and we spent the meeting talking about their situation instead of throwing up all over them about what we do."  Jamie is a HERO. His world revolves around delivering customer value, and he has neither the time nor the patience for anything that gets in the way.

Naturally, I asked him some questions about his MacBook Air and the applications he uses. His answers, while fascinating, echo what I hear from many others like him:

Q: How do you like your MacBook Air?
A: I love it.
Q: Does your company issue those or is that one yours?
A: Hell no! It's mine! They gave me a huge Dell.
Q: Where is it?
A: It's in the closet at home, still in the bag.
Q: Does your company support the Mac?
A: Nope. I'm on my own.
Q: What about getting on the network and using e-mail and the salesforce automation tool?
A: I just use webmail on the Mac and we use salesforce.com. They helped me get my iPad set up with e-mail though.
Q: Don't you guys have other apps on the network that require Windows?
A: Yeah, but I just don't use them.
Q: Doesn't that get you in trouble with your boss?
A: As long as I'm blowing out my number, he doesn't care what I use.
Q: What if you have a problem? Don't you call the helpdesk?
A: Nope, if I have a problem with the Mac itself, I go to the Apple Store. The only time I call our helpdesk is when I can't get access to something.

Jamie has the skills to make his own technology choices. His talents are hard to find and he is expensive to replace. His exceptional performance in his job means that his executives know who he is and he will be given the power to overrule the IT hierarchy and use whatever helps him stay productive.

When I talk with I&O professionals about people like Jamie, they're often horrified. "That guy is setting a bad example for his team!" or "He needs more support than he admits!" or "In this economic climate, I have absolutely no interest in supporting new platforms!" This last one I heard just last week, and I asked: "Really? So you think your HEROes should be reined in or reprimanded?" "Absolutely! That's why we have policies!" "I see. What if they leave the company because they're frustrated with how the company supports his efforts?" "I'd say good riddance!" Wow.

Similar lines of thinking are rampant in I&O organizations everywhere. We have gone from a culture of service 15 years ago, to a culture of standards and control today. Removing all sources of risk and threat has taken priority over people-centric customer service and enablement, and people like Jamie see their I&O organizations as unhelpful…so they banish them from their working lives. We need look no further to understand the nature of consumerization and who's driving it. The situation has to change, and I&O organizations will be forced to find ways to deliver both freedom and security. Jamie's demographic holds a tremendous amount of power in business.  This idea is the subject of much thinking and research here at Forrester.

The days of what I like to call "Henry Ford's IT" — where people can have corporate technology in any color they want as long as it's black (a reference to the Ford Model-T sold in only one color) are over.  The successful I&O professionals of tomorrow will be a master of delivering freedom AND security, and will be doing it with less than they have today.

What do you think? Is aligning with what Jamie needs or wants the same thing as aligning with the needs of the business? Does Jamie need to re-align with the policies and practices of the business, or does the business need re-aligning with Jamie?