Put yourself into the position of your CEO. He rubs shoulders at various functions and places with other business owners and CEOs and VIPs. He’d *love* you if he were the one showing off the newest awesome technology to his peers, rather than the one oogling someone else’s gear that *their* staff succeeded in implementing. Better yet if he can actually do work conveniently and securely! The same goes when he and 3 competitors are offering presentations to a prospective customer, and he simply has better technology to show off (either on his person or in the demo).

It really comes back to one of those rules of business: always make sure your manager looks good. Don’t be the person who makes your manager look bad.

Of course, this whole circular problem with managers (consumers) influencing each other and bringing in technology ideas to the corporation and thus bogging down IT and security is a problem. But some problems none of us may end up solving unless we’re in a hard-and-fast regulation-driven organization housed in the Pentagon.

In that case, keep in mind that you can make allies by running ahead of the curve. Just make sure if you stumble a few times, you only scrape your knees rather than take your whole team out of the race.

(I know, it depends on your culture and CEO personality. For many, trying and failing now and then is valuable as opposed to not trying at all. But for some, trying and failing in front of the CEO is just as much a career death knell as anything, no matter how gracefully you handle it.)