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With the election over, the world’s opinionators have switched their opining from comparing candidates’ horse-race strategies and tactics to pointless post mortems on the same subject.

Pointless because the correct analysis is, what was Clinton thinking, setting up her own email server instead of using Gmail like everyone else?

Last week I promised to get back to business. I am. Because if you filter out all the noise, the Clinton Email Fiasco provides plenty of guidance for the world of organizational dynamics.

Start with an excellent long-form piece by Politico’s Garret Graff titled “What the FBI Files Reveal About Hillary Clinton’s Email Server” (9/30/2016). According to Graff, the FBI’s investigation documents “… depict less a sinister and carefully calculated effort to avoid transparency than a busy and uninterested executive who shows little comfort with even the basics of technology, working with a small, harried inner circle of aides inside a bureaucracy where the IT and classification systems haven’t caught up with how business is conducted in the digital age.”

In broad brush if not detail, the story should sound familiar. Start with Clinton’s technical illiteracy. She apparently doesn’t even know how to use a personal computer. For email, she once learned to use a Blackberry and that was the beginning and end of her tech savviness. Even her staff’s attempts to move her to an iPad or iPhone died on the vine.

Couple that with the sheer volume of emails she had to contend with — you’ll recall they numbered in the hundreds of thousands. Next mix in that the State Department’s secure email facilities were clumsy and antiquated. And that in addition to her Blackberry, Clinton managed much of her email traffic by having aides print out messages for her to read and hand-write responses. But outside the State Department’s facilities this couldn’t be done, so her staff forwarded emails to her private server as a workaround so they could be printed.

The punchline: Substitute your own company’s less-than-tech-savvy executives for Hillary Clinton. Substitute inconvenient or hard-to-use information technology for the State Department’s secure email system. Substitute Gmail and Dropbox for a privately managed email server.

And finally, substitute your technology-use policies for the State Department’s technology-use policies, and your insufficient technology refresh budget for the State Department’s insufficient technology refresh budget.

Get the picture?

Outrage is easy when someone in authority violates the policies everyone else is expected to follow. Empathy is harder.

But as any good business analyst will tell you, empathy is the essential ingredient in information technology design. “Documenting requirements” only gets you so far, as anyone knows who has documented the requirements for secure passwords will tell you. Those requirements are precisely what cause employees to write down their passwords on easily-found Post-It notes.

People have work to do. Executives are people too, often with bigger piles of work than anyone else. And character flaws notwithstanding, your typical executive mostly gets it done.

Executives are, if anything, even more impatient than anyone else regarding obstacles that keep them from doing it.

Regrettably, in my experience at least, at a personal level more executives see information technology as obstacle than see it as an assist, so while they might not be so extreme as to not know how to use a PC, there are plenty who won’t take the time to learn (for example) how to track changes in Word; to use SharePoint in its usual IT-friendly/user-unfriendly configuration; or to use the company’s web conferencing system’s whiteboard feature to facilitate mixed in-person/remote participant meetings.

Not to mention … it’s a whiteboard. How many employees at any level have PCs that let them use a stylus to draw on the whiteboard?

Answer: Very few, because of the rarely recognized chicken/egg nature of so many IT requirements: Few people ask for something because they don’t know it exists; IT doesn’t offer it because nobody asks for it.

So … where does the Clinton Email Fiasco take us?

It’s past time for businesses of all kinds to recognize that inconvenient IT, especially when coupled with a lack of technology savviness, constitutes a significant risk to the business.

Even more, it’s long past time to recognize that dealing with most risks by establishing policies are little more than CYA strategies. They’re pretty much worthless when it comes to preventing or mitigating the risks themselves.

While in your case the fiasco will be less obvious and visible, the lesson is nonetheless just as consequential when profits and brand are at stake as for more minor matters like appealing to voters.

Comments (11)

  • EXACTLY my thoughts re: the whole Clinton email scenario, right down to the ‘oh, s__t’ moment, when the IT guy realized he hadn’t deleted the emails when he was supposed to. (Now to figure out how to post your piece on LI.)

  • Bob – I partially agree with you. I’m all for friend and easy to use solutions that meet the business need. My current struggle is auditors, those pesky people that come out and do everything possible to make access to data difficult. In the trenches we are fighting a daily war between cybersecurity and ease of use. My guess is Clinton ran into this exact problem. Believe it or not, by last audit busted me for allowing access to DropBox from our network. We explained a number of people use it to interact with partners and vendors. Still no dice but I haven’t turned it off.

  • Bob: Your usual sideways look at the issue…makes you think. Thanks!

  • I disagree with most of what you said. You make the statement “Start with Clinton’s technical illiteracy. She apparently doesn’t even know how to use a personal computer”

    While poor technology can hamper accomplishing a mission or a set of goals, email is not new tech. It has been around for decades!

    Whatever happened to personal responsibility. Would you want a mechanic to work on your car who did not know how to properly use the tools needed to get the job done correctly and safely? In this day and age, email is one of those tools!

    How could a proclaimed world leader in this day and age, not know how to use basic technology?

  • Thanks for this week’s article. I found it very informative, but I do have few questions and/or comments:

    1. “Pointless because the correct analysis is, what was Clinton thinking, setting up her own email server instead of using Gmail like everyone else?” Point of information – Is this gmail.com? I don’t expect it is, but I would have found a few words of explanation helpful for those of us who have never worked for the government.
    2. You wrote, “Start with Clinton’s technical illiteracy. She apparently doesn’t even know how to use a personal computer. For email, she once learned to use a Blackberry and that was the beginning and end of her tech savviness. Even her staff’s attempts to move her to an iPad or iPhone died on the vine.” – If this is true (and, apparently this point has been exhaustively documented), why are you, as well as almost everyone in media, infuriated with her? Did her boss, the President order her to keep her server on the State Department computer network? Did the Director of IT services consider her practice to be of such a significant risk that he offered his resignation after repeated warnings on this issue?
    If not, why are you and others so angry at her? She. Is. A. Lawyer. She. Is. Not. A. Computer. Geek. Like. An. IT. Person. Would. Be.
    She is an expert in foreign affairs. She has tremendous expertise in civil rights, women’s rights, and children’s rights. She has expertise in national health care and investment banking policies. She is exceptional at developing policy and breaking down barriers – these are facts, no matter how you feel about the consequences of this actions. But, by your own article, she has no more expertise in network security than a senior network technician or administrator would have in filing a civil rights appeal or presenting a closing argument to a jury, and has never claimed otherwise.
    So, I ask again, where does this persistent, intense and judgmental anger at her come from? You probably know that Albert Einstein and Michael Faraday were lousy at math, but pretty good at physics. History seems to have been pretty kind to both of them, despite their lack of inner math vision.
    I personally feel that the consequences of this election will have grave consequences for our country, so I’m not real happy about that and I just want to understand. I’ve always felt you were exceedingly fair in your analysis, but this really feels like the application of a double standard because she is a white middle-class (older? [my age]) woman. I honestly can’t see anything else. Can you help me see what I might be missing, other than the fact that no one is perfect?

    • Not sure where you detected intense anger on my part. Personally, I’m appalled at the election results – less because of who was elected; more because hate and anger were the clear winners and what that says about the electorate.

      But … the email server was just about the only issue with any substance at all to it raised against Clinton. Setting it up was a bad idea, and she handled the fallout just about as badly as I’ve ever seen a candidate handle something like this. I’ve talked with quite a few folks who voted for Trump, and read the comments of innumerable others. Almost without exception the email issue was front and center in their decision-making.

      But regarding tech illiteracy, this is, what, 2016? There are basic tools of the trade it’s reasonable to expect any modern manager to have mastered by now. Clinton hasn’t. She has many fine qualities. This isn’t one of them.

      • Thanks for your response. To be clear, Clinton, like me, is a class of ’69 graduate, from a good school. Do I wish she had been even marginally computer literate? YES!!!, for a million (or, perhaps, 350 million) reasons. But, I have the somewhat unique experience and recent experience of working with about 3,000 in 70+ K-12 students while also working with a fair number of X-Gen and some Millennial molecular biologists and biochemists involved in basic research, as a part-time bioinformaticist during the same 5 to 7 year period as I was substitute teaching to make ends meet.

        And, except in the very best schools, would I say more than 30% percent of those academic populations is even moderately computer literate, apart from using their smart phones, a word processor, or spreadsheet.

        But as I write this, it occurs to me that I can’t think of any super-users I had in the 4 different companies and the 500 users I had partial or total user management responsibility for, except in an architecture department, who could really “get” server security, let alone evaluate it.

        Believe me when I say that the systems administrator/tech support person within me agrees with what you wish were true of users, whole-heartedly. I think your article helps constructively address many aspects of what I have come to believe is a non-trivial problem.

        However, since the FBI concluded that her server never was broken into, as far as could be determined, in my opinion, it is a lack of literacy about what demagoguery is, how to recognize it, how to counter it, and how to legislate needed protections, given an effective understanding of that we need to be concerned about, rather than Clinton’s computer literacy.

        Outside of my own “brilliant” thinking, I didn’t see one media article addressing this issue, though there will be hundreds addressing its consequences. Did you or anyone see such articles in this election? And, if not, why not, given the huge volume of hate speech and hate tactics utilized in this election?

        Again, thank you for taking this topic on, in such a constructive way.

  • Today’s highly segmented media environment provides all of us with an easy choice of an echo chamber to reinforce and amplify for our own views, fears, and proclivities. Add to that confirmation bias and selective listening, and we come right up to my read on this particular Bob Lewis piece. So with my selection bias noted, I really appreciate this column.

    If IT can’t make the right choice the easy choice, technology users will often not suffer the inconvenience of making the right choice.

    For those of us who work in an environment where the risks of Dropbox, Facebook, or self-service SaaS without contract protections are unacceptable, we have to provide modern, easy-to-use tools that will approximate the convenience of these tools. IF we do not give them an easy way to do what they need to do, resourceful people will find a way.

    Most people, given appropriate information, will work a little harder to do the safe thing, but not a lot harder.

    Great column, Bob.

  • In your previous column, you wrote: “We appear to have a national consensus on the most important issue: Is this the best we can do?” echoing a common feeling that both major nominees were equally appalling (people voting for a meteor strike in preference, etc.)

    But I never understood why people were so horrified by Hilary Clinton. When she was running against Obama for the Democratic nomination, there was no feeling like Democrats were forced into choosing the lesser of two evils. Instead, it seemed like they had two solid candidates and got to pick which was the best.

    Now that was eight years ago, and since then she’s held the high profile and extremely challenging position of Secretary of State.

    In this column, you do an excellent job of dissecting the reasons behind the email fiasco, which were pretty much the same reasons I’d come up with. The email issue was extensively and exhaustively investigated by the FBI, which determined, seemingly against the FBI Director’s preference, that no crime was committed.

    And yet based seemingly on this one scandal, choosing Clinton was put on par with selecting a hate-filled vitriolic demagogue with no relevant experience, who called failing to pay workers and tax-dodging “smart business”.

    So it leaves me wondering, was Hilary Clinton really considered so vile an option, if evaluated on her own merits? Sure she wasn’t perfect, she had flaws, she’d made mistakes before and she was bound to make more (anyone not living in a glass house, feel free to throw stones). But if you are waiting for an election between two perfect candidates you’ll be waiting forever.

    Was it really 8 years of collecting more political scandals that turned Clinton from one of two decent choices into an “I’d rather face apocalypse” option; or was it the candidate that she was facing?

    I wanted to turn this question into an IS/IT/business-related one, but have been unable to come up with an example of a business actually having a decent choice, but that just looked bad lined up against really poor option(s).

    Have you ever come across a situation like this? Anything like it worth addressing in a column?

    I’m thinking, perhaps, that consultants often get a bad rap – collect a lot of money for not producing much value. I’m sure there are lots of opportunistic consultants out there; do they taint the reputations of the consultant(s) who’d be beneficial? Or companies who don’t make the best use of the value that a consultant does provide (consultant creates an excellent report; it sits on the shelf collecting dust instead of being implemented; company vows never to hire a consultant again).

    Or any other more relevant example you might know of (maybe there isn’t one, I don’t know).

    • I wasn’t horrified by Clinton, but I was disappointed that she was the best the Democratic party had to offer. Ignore the real and putative scandals – they ranged from phony to minor, in my estimation. Ignore her nearly textbook perfect exactly wrong way to handle them.

      Instead, ask yourself what new or interesting ideas Clinton brought to her campaign. I didn’t hear anything that wasn’t the same tired old stuff. Leaders have to set direction, and “more of the same” is pretty weak tea when it comes to setting direction.

      Also – don’t ignore her nearly complete unwillingness to hold press conferences. Clinton needed to be out there, making it clear she, unlike her opponent, was perfectly happy to talk to the press, take their questions, and actually answer them.

      Instead … nada, or nearly so.

      In my estimation, Clinton would have made an outstanding chief of staff. As a president she would have been competent, which is no small thing.

      Finally, ask yourself this: Who do the Democrats have waiting on the bench, ready to run next time? There’s Elizabeth Warren, who will be 71 years old when the next election rolls around. Beyond that, the best I can think of are our two senators from Minnesota, and I’m skeptical that either Amy Klobuchar or Al Franken are really presidential material.

      Compared to the guy who just got elected, of course they are. But compared to, say, either Roosevelt, Truman, or even Ike Eisenhower? Kennedy? Bush #1? Bill Clinton?

      But then, I’m no expert on these things. You did ask, though.

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