Keil Hubert: Don’t Ask Alice

Has your CXO ever thwarted a critical IT initiative using phrasing that’s clearly not their own? Business Technology’s resident U.S. ‘blogger Keil Hubert discusses the insidious practice of using lies and misdirection to secure personal advancement through indirect character assassination.

Take a covert look around your office. Is anyone watching you? If you’re (momentarily) safe from observation, let me ask you something: have you ever had a tech initiative scuttled by someone outside of the IT department who had undue influence over your executives? Don’t laugh! They might hear you… Just smirk into your hand. We’ll keep it our secret. I know…  It’s happened to all of us in the industry at one time or another. I feel your pain, compadre.

If you’re not one of those veterans of the IT trenches, let me prognosticate a small (but painful) element of your future: someday, no matter how careful you are in your preparations, your boss is going to veto a perfectly-obvious, self-evident, cost-effective, and critically necessary tech change request because he or she ‘heard that’ your proposal is somehow a bad idea. Your boss won’t have any actual hard facts to support their position, and they’ll be extremely evasive when you press them for the source of their position. You’ll walk away, thwarted and frustrated, completely flummoxed by your boss’s utterly indefensible stance.

This is a far more common occurance than logic would suggest is reasonable in a rational organisation. What this happens, it means – in the most blunt of terms – that the executive holding dominion over the IT department has begun to distrust his or her IT experts. Maybe they think that you’re lying to them. Maybe they suspect that you have an insidious hidden agenda. Perhaps they completely misunderstood something you said and confused an innocuous technical term for something prurient. For whatever reason, your boss went outside their official IT channels and ran your proposal by their tech-savvy ‘mate’ in another division – and that guy or gal took advantage of the opportunity to advance their own agenda to savage both you and your idea to your boss. That weasel sabotaged your initiative without you ever knowing that they had an objection – and your boss believed his or her favourite weasel’s opinion more than yours.

In Texas – in my circles, at least – we nicknamed this ‘Alice Syndrome’. It’s derived from the 1971 novel Go Ask Alice. When the book first came out, it was advertised as the actual diary of a teenage girl who flirted with drug abuse and wound up overdosing. American schoolteachers embraced the book for its strong anti-drug narrative – I remember finding a copy of the paperback edition in my bloody elementary school. As Dr. Barbara Mikkelson [1] of Snopes.com fame framed it:

‘Drugs were on the minds of everyone in the late 1960s and early 1970s, even those who weren’t partaking of illegal substances or harboring plans to ever do so. Paternalistic concern about the burgeoning drug culture led to the youth of that day being heavily indoctrinated with anti-drug propaganda at almost every turn — particularly in school, where they were subjected to health classes which were little more than “don’t get high” lectures. Even the selection of recreational reading materials intended for them was booby-trapped with literary offerings purporting to be true life stories of real kids yet which were no more than “This is what could happen to you” sermonizings.

‘The most famous of these literary works was 1971’s Go Ask Alice, presented as the diary of an anonymous teen girl who began her career as a stoner at age 15 and died of an overdose just weeks after her 17th birthday. Through the diary entries we see this girl quickly escalate from her first drug experience (LSD was surreptitiously slipped into her Coke at a party) to all manner of disaster…’

That’s how drug use works when you’re a teenager, right? You take LSD once, and then you freeze to death in the wreckage of your private aircraft just outside a secret Nazi missile base in the Antarctic. I never experimented as a youth, so I’m a bit unclear on the sequence.
That’s how drug use works when you’re a teenager, right? You take LSD once, and then you freeze to death in the wreckage of your private aircraft just outside a secret Nazi missile base in the Antarctic. I never experimented as a youth, so I’m a bit unclear on the sequence.

The key phrase there is ‘presented as’… There actually was no diary. The whole shebang was invented, whole-cloth, by a middle-aged woman named Beatrice Sparks. As Lina Goldberg explained in her essay ‘Curiouser and Curiouser’: Fact, Fiction, and the Anonymous Author of Go Ask Alice:

‘In 1979, eight years after its publication, in an interview in School Library Journal with Alleen Pace Nilsen, Sparks admitted that although there was a real “Alice”, Sparks had added other incidents and ideas inspired from similar case studies.’

Ms Sparks went on to write eight other ‘teens who saw their lives ruined by their bad choices’ genre stories after GAA’s commercial success. [2] Sparks tried to claim that she was only the ‘editor’ of the real Alice’s diary, but experts rightly didn’t believe her. The story reads like a 50-year-old writer pretending to be a teenager. Sparks tried to claim that she couldn’t find the original source materials, and didn’t want to identify the actual subject. Then she changed her story about Alice having died of an overdose to having died of ‘natural causes’, but still didn’t want to reveal the subject’s actual identity. Ms Sparks came across as evasive, exploitative, disingenuous, and not at all credible.

Re-stated in the most charitable fashion, a woman who held a very strong (presumably well-intentioned) opinion on the negative effects of drug abuse decided to attack the problem through thinly-veiled fiction. She created a fake ‘diary’ that purported to tell the story of a typical American teenager who abused drugs and came to a bad end. Perhaps she felt (again, reasonably) that her audience would be more receptive to a cautionary tale told by ‘one of their own’ than they would be to yet-another dry lecture delivered by an older person who couldn’t relate to youth culture. I give her efforts – at best – a B for compassionate intent, and a D- for sloppy execution.

Alice Syndrome (or whatever you call it in your company) most often manifests in the form of a tactical gambit – a fraud – that’s perpetrated through intermediates in order to stop someone else from doing something that the perpetrator opposes. Say that your CFO is very comfortable with Microsoft Excel 2007 and doesn’t want to upgrade. When she learns that you, in your role as head of IT, intend to force all of your companies to upgrade to Office 2013, she engages in a little Alice-ing by whispering to the CEO that Excel 2013 has been ‘proven’ to cause cancer in rats. It doesn’t matter that the heart of the story is utter b******s; once the target audience (the CIO) comes to believe the teller’s core message (i.e. that Excel 2013 is A Bad Thing), he or she becomes poisoned against your upgrade proposal and won’t hear any more about it.

Hear No Evil - White Businessman Covering Ears Desk
‘Don’t start with me about patching, either. I’ve recently learned that Zero Day Vulnerabilities keep you from going impotent.’

If that was all there was to the syndrome, it’d be relatively easy to contain: specious logic can be exposed as such with facts, rational dialogue, and other conventional business tactics. There’s more to the problem, though… Sometimes, Alice Syndrome is perpetrated for more cynical and destructive ends. People being people, some clever employees will embrace this tactic for strategic gain. They become consummate, opportunistic generators of balderdash – not just to interfere with your endeavours, but also to curry favour with the powerful people in the company, so as to secure themselves a purely personal advantage.

I dealt with these professional Alices frequently in my various roles as a head of IT. In one of my organizations, the members of the manufacturing arm of the company dominated all of the key leadership positions. If you hadn’t come from the factory floor, you didn’t have a hope in hell of scoring an executive billet. All of the executives knew each other, because they’d all come through the good-old-boy pipeline together. That meant that their primary loyalties were to other members of the brotherhood, not to the business or to the line employees. It also meant that the Top Fellows [3] double-checked their difficult decisions with the other made-men rather than with the actual, paid experts in a given subject.

I had to regularly grapple with my own Alice: a recurring thorn in my side from the factory floor who delighted in subtly thwarting every major upgrade that we attempted to launch. This fellow would slow-roll the deployment of new equipment to his users, would trash-talk the IT team among all the users, and made himself ‘available’ to the CEO to weigh in on IT issues that he himself had no knowledge of or experience in. He took a little boy’s sick pleasure in making life unnecessarily difficult for the back-office support departments, whether finance, human resources, supply, or IT. We eventually reached a point where Alice mitigation became a standard element in our project planning efforts.

One of Alice’s [4] favourite dirty tricks was to case aspersions on the motivations and competence of the IT staff when systems didn’t work. His most common fake complaint was directed at the data network infrastructure – when his department’s PCs took a bloody long time to boot up, he complained to all and sundry that ‘the IT people’ were ‘deliberately slowing down the building’s network connection because they hate us’. He repeated the same lie so many times that we started hearing it from dozens of disaffected users – users that were all ‘in the brotherhood’, and would leverage their special status to interfere with support operations. His people undermined attempts to fund various projects, whispered poison into the CEO’s ear at department parties, and did everything that he could to get other people to put obstacles in our path.

‘I’m onto you, laddie! I … heard … that the "cloud” where all our servers live now is actually comprised of invisible nerve gas."
‘I’m onto you, laddie! I… heard… that the “cloud” where all our servers live now is actually comprised of invisible nerve gas.”

When we challenged Alice to defend his accusations, he claimed that all of the PCs in his building took twenty minutes each to boot. We put his claims to the test with known-good PCs and discovered that there was a ~30 per cent increase in boot times for their machines compared to the PCs in the rest of the campus… but not 20 minutes’ worth of delay. Also, the ultimate source of Alice’s ‘slowdown’ wasn’t the campus’s network infrastructure, since his entire building used less than 7 per cent of their available bandwidth to the campus data centre. No, we discovered that the cause of his ‘catastrophic’ work stoppage was the poor performance of a departmental server inside his building that he, himself, had insisted that his all personnel connect to at startup. Put bluntly: Alice had manufactured his own crisis, and then used it to hypocritically throw shade on IT.

Give my Alice some credit: the fellow wasn’t stupid. He’d worked out that he could secure a stronger political position with the ruling elite than his peers by opportunistically disparaging the ‘lesser departments’ to the executives. He fed the executives’ paranoia that all of the other service providers were jealous of their success, and suggested that all of us filthy proles were secretly plotting against the throne. If you’re a Tolkien fan, picture our Alice playing the part of the caustic and conniving Gríma Wormtongue to our CEO’s King Théoden of Rohan: he gave good service to the business once, but worked covertly to undermine the organisation to facilitate his own advancement.

Fair warning: if you work for a business that has more than two-dozen employees, rest assured that you’ll inevitably have these people in your company if you don’t already. Odds are, you have an Alice or three already in the ranks, and you just don’t realize it yet. See, there’s a natural human tendency to rationalize unethical behaviour when it’s deployed in the service of a ‘higher purpose’. Personal advancement and job security are often two of the highest purposes motivating individuals in the modern economy – workers are constantly trying to position themselves one step ahead of the next round of layoffs. If they can’t secure a defensible billet through talent, then (they rationalize) it’s morally acceptable to secure said billet through subterfuge. Likewise, people in reasonably secure positions will morally justify engaging in subterfuge to get themselves a better billet. These actions may be initially inspired by existential dread; over time, they’re fueled be simple greed.

As Dr Keegan wrote in The Psychology of Fear in Organizations: Greed and fear are lethal bedfellows. They stoke the flames of paranoia, often fuelling toxic cultures in the process.’ Whether your Alices are primarily motivated by their own fear or greed, their approach to life is to spin opportune situations to appear much different than they really are in order to play on others’ fears. They mask their own motivations and misrepresent events to indirectly stain the reputations of other team members. Alice comes off as the ‘good friend’ who ‘has the boss’s back’ against internal threats that don’t actually exist. Those leaders then reward Alice with money, promotion, greater autonomy, and (worst of all) greater access to the C-suite.

… where they can leverage their access to inflict even more damage on their potential rivals.
…where they can leverage their access to inflict even more damage on their potential rivals.

Dealing with these bloody insidious people is extraordinary vexing, since it’s often very difficult to catch them it he act. They tell their lies in private conversations and under controlled conditions. They couch their ‘advice’ in such a way as to convince the recipient that it shouldn’t be attributed to them. They carefully avoid leaving documentation trails, preferring hallway chats to incriminating e-mails. For all practical purposes, they’re self-appointed agents provocateurs, enticing other people to conduct reprehensible acts while keeping their own reputations clean.

Therefore, it’s critical to your survival and effectiveness as a head of IT to identify your potential and realized Alices as swiftly as you can. You can’t effectively defend yourself from adversary action that you don’t realize is occurring. The best way to identify these fiends in saints’ vestments is to pay very close attention to strange phrases that come out of your top executives. Whenever your executive makes a statement in regards to something within your domain that seems oddly incongruous (given their education, background, technical proficiency, etc.), assume that he or she didn’t come up with on their own: start pressing (as best you can) for the originating source of the opinion. Leverage your good relationships with secretaries, aides, and other line-level workers to learn who the executive takes his or her advice from, or who-all they pal around with.

Once you’ve identified your potential adversaries, find a way to engage them. Draw them out. Get them engaged in conversation to glean clues as to their motivations. If they come right out and express anger with you or your people, then you have a critic – not an Alice. If, however, your target seems congenial and smarmy, accept that you probably have an Alice on your hands. Confronting them directly isn’t going to make them back off – these are opportunists who prefer to strike at you indirectly. They’ll vehemently deny any charges that you level, and will likely put on a very good show of feeling hurt by your mistrust.

I’ve found that there are only two effective approaches to mitigating an Alice, assuming that you can’t get them sacked. If your circumstances require you to suffer an Alice to live, then subtly manoeuver them into exposing themselves – engineer a situation where you catch them committing an inappropriate act. This allows you to discredit any and all of their negative statements as the sullen ranting of a known-malcontent. Failing that, you put extra effort into ‘inoculating’ your boss against your Alice’s likely arguments. Deduce how your Alice likes to spin things, and then present your program to upper management with a counterargument for Alice’s inevitable complaints.

Over time, you may wind up investing more time strategically preempting your adversaries’ potential moves than you spend developing actual IT solutions.
Over time, you may wind up investing more time strategically preempting your adversaries’ potential moves than you spend developing actual IT solutions.

Just be aware that using your Alice’s tactics against him or her is only going to be effective for a few skirmishes. Once they catch on to what you’re doing, they’ll usually withdraw deeper into the shadows, and will change their own tactics to regain the initiative. You’ll wind up playing a long cat-and-mouse game with them, like one of John le Carré’s spy-catcher thrillers. This can – I’m sorry to say – go on for years with neither of you gaining the upper hand.

That’s the final reason why we nicknamed this insidious behavior ‘Alice Syndrome’… Go Ask Alice is still being taught in American public schools, even though it was discredited as a work of fiction many years ago. Well-meaning teachers continue to wield the book’s wholly-fictional morality tale as a bludgeon against what they perceive as decadent youth culture. So, too, your office Alice will likely continue to bedevil your operations with his or her clever little lies for months, or years, or even across overlapping careers. To make things worse, cutting the head off of one such Alice doesn’t permanently end the problem – dispatch one, and another will fill the void before you’d had time to clean your allegorical blade. Fear and greed are omnipresent in the modern business environment, and no opportunity for interoffice mischief goes unexploited for long. There’s always going to be someone to appreciates the potential for personal gain, to be secured at very low risk, and tries their hand at a bit of anonymous fiction.


[1] For disclosure’s sake, I’ve been a fan of Dr Mikkelson since the late 1990s when I first started studying urban legends. I negotiated with Dr M for permission to reference her work over at snopes.com for the Texas Air National Guard’s ‘Rumour Control Line’ during the post-9/11 period, when our deploying soldiers and their families were inundated by hysterical fear-mongering coming from well-meaning friends and relatives by way of the Internet.

[2] Dr M’s word choice. I could not have done better. <tips hat>

[3] There were no ‘Top Ladies’; the reigning good-old-boy system was strictly a brotherhood.

[4] Not his real name, obviously.


POC is Keil Hubert, keil.hubert@gmail.com
Follow him on twitter at @keilhubert.
You can buy his books on IT leadership and IT interviewing at the Amazon Kindle Store.

Keil-Hubert-featuredKeil Hubert is a retired U.S. Air Force ‘Cyberspace Operations’ officer, with over ten years of military command experience. He currently consults on business, security and technology issues in Texas. He’s built dot-com start-ups for KPMG Consulting, created an in-house consulting practice for Yahoo!, and helped to launch four small businesses (including his own).

Keil’s experience creating and leading IT teams in the defense, healthcare, media, government and non-profit sectors has afforded him an eclectic perspective on the integration of business needs, technical services and creative employee development… This serves him well as Business Technology’s resident U.S. blogger.

Keil Hubert

Keil Hubert

POC is Keil Hubert, keil.hubert@gmail.com Follow him on Twitter at @keilhubert. You can buy his books on IT leadership, IT interviewing, horrible bosses and understanding workplace culture at the Amazon Kindle Store. Keil Hubert is the head of Security Training and Awareness for OCC, the world’s largest equity derivatives clearing organization, headquartered in Chicago, Illinois. Prior to joining OCC, Keil has been a U.S. Army medical IT officer, a U.S.A.F. Cyberspace Operations officer, a small businessman, an author, and several different variations of commercial sector IT consultant. Keil deconstructed a cybersecurity breach in his presentation at TEISS 2014, and has served as Business Reporter’s resident U.S. ‘blogger since 2012. His books on applied leadership, business culture, and talent management are available on Amazon.com. Keil is based out of Dallas, Texas.

© Business Reporter 2021

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