Why Jon Stewart should be CIO of the U.S. government

I used to do email audits, and I’ve been up to my armpits in email system selection and controversy most of the time I’ve been an analyst. For those reasons, I very much enjoyed Jon Stewart’s coverage of the Hillary Clinton event Wednesday night where he was asking the questions any good IT Auditor or CIO should be asking when presented with the concept of a private email server, particularly after the fact.

[Related: Hillary Clinton is now the face of shadow IT ]

Jon is about to step down from the Daily Show, maybe his next job should be CIO for the U.S. government, based on the current problem, he’s probably better than who they have. Let’s talk about this and executive privilege, which goes to the core of this problem.

Looking underneath the excuse

What Stewart did was to look underneath Clinton’s reason for the personal email server and correctly pointed out that it was invalid. That is always the best way to deal with an executive privilege issue, to point out why the executive shouldn’t want the unique privilege. In this case, with a government server and two phones what is personal stays personal, and what is private stays private. The convenience of one phone doesn’t offset the problem of separating out 30,000 emails or having to have someone else read all of the emails to find that 30,000.

And, of course, the ongoing implication that some subset of the 30,000 emails might have seemed incriminating and prevent her presidency would have been an added bonus. Stewart correctly used the first example to showcase that Clinton’s desire to have a personal email server was a bad idea, not for the U.S. (which it clearly also was), but for her.

At this point, the smart IT auditor would also look at voluntary executive behavior, and Stewart correctly pointed out that now that Clinton is back in the private sector she has two phones so that her email is again separate at the source. This suggests her real reason wasn’t convenience at all and that it’s likely the real reason wouldn’t be acceptable to executive management.  

[ Related: Some email truths for Hillary Clinton ]

Granted as the CIO, Stewart making fun of her would only cause trouble and surely wouldn’t ensure his long-term tenure, it would probably only endear him to Clinton’s peers and his own subordinates who would miss him once he got fired.

It would be worth the price of admission to go to one of his meetings, though. But executive privilege can be a nightmare that never stops giving. I’ve seen a number examples over the years.

Executive privilege

The worst example of executive privilege I’ve seen, and I’m talking about executives who can do things that others can’t, was a CMO at Novell years ago who had built into her contract that she flew first class or on private jets, and got a limousine. Even when going from building to building, where most folks walked, she’d have her limo pick her up and drop her off. This pretty much alienated everyone and she failed miserably in the job.

A few years back Intel got a new CMO and he decided he deserved an office, even the CEO at Intel has a Cubical, so he took over a conference room and even had his staff go into a different conference room where he’d call in from his “office” for meetings. This tended to alienate everyone, including the folks he reported to, and that didn’t end well either.

Executive privilege, specifically the violation of policy or practice, for someone of power almost always ends badly. Stopping the practice of exploiting privilege involves finding a way to make the executive aware that it will end badly for them. And while Hillary can point out that others before her used private email servers, the counter argument that they hadn’t planned on running for president likely should have given her pause and avoided this problem.

Jon Steward for president

I really like the idea of having Jon Stewart in some government role because sometimes laughing at some of the insane things that politicians do is the only way to ensure sanity. But his core example of showcasing why an executive shouldn’t do something, not because it is against policy, which they often think they are above, but because it might damage their long-term career goals or current status is to point.

Executives, when they are thinking, tend to be protective of their careers. In order to keep them from doing something stupid, one of the best paths is to show them the likely personal adverse result of what is often a misuse of power.  

So, given the problems identified with Hillary Clinton’s email and a clear abuse of executive privilege, and partially because Jon will need a job shortly, I think he should be CIO of the U.S. Government as, clearly, we have had worse. At least Jon is funny.