q The American View: A Literal Education - Business Reporter

The American View: A Literal Education

Imprecision in language is one of the worst traits that a leader can possess. Business Reporter’s resident U.S. ‘blogger recommends hiring an annoyingly clever person to force you to communicate clearly by confounding you whenever you get sloppy. It’s the only way to learn.

My son Austin came home from university last Thursday wearing a satisfied smirk. He seemed ready to burst with barely-contained mirth. I obligingly asked him how his day had gone and that set him to cackling. It seemed that he’d driven his psychology professor to drink by creatively fouling up her poorly-worded class project.

He showed me his handout from the class’s exercise. One side had a grey square with three rows of three dots each. On the other side were the instructions: ‘Please connect all of the dots together using at most four straight lines.’ I groaned. This was the classic ‘think outside the box’ logic problem from late 1990s business consulting, and it wasn’t well presented [1]. I didn’t need to look at his solution; I know my son. His dot-grid was connected by a meandering collection of six wriggling lines … A completely fair solution, given how poorly the instructions had been phrased.

Per Dr. Marcel Danesi, writing in Psychology Today back in 2009, the phrase ‘thinking outside the box’ dates back to World War I. The nine-dot puzzle – where a clever student is supposed to draw an umbrella shape – got popular in the late 90s as a way for shiny-suit consultants to wow their victims clients with their superior thinking skills. Because of humans’ natural tendency to perceive the edges of the grid as an impassable boundary, there’s no obvious way that four connected lines can cross all nine dots.

Unless you want to get into multi-dimensional maths.Not that we have many ’safe’ topics left to discuss after the last year in international politics.  

That’s the ‘teaching’ part of the puzzle. That‘s why instructions are supposed to be phrased Without letting your pencil leave the paper, draw four straight lines through the following nine dots.’ When the presenter extends one of the straight lines well outside the dot grid to return at an angle against the opposite side dots, it seems immediately obvious and surprising at the same time (if you’ve never seen it before).

My son comes by his humourist streak honestly. He saw a flaw in the professor’s instructions, and he exploited it for his own fiendish amusement. [1] As did I. I hated this cute consulting trick when it first came out, because it’s condescending doesn’t truly teach what it’s intended to convey. That’s why I used to enjoy torturing the underqualified and overconfident confidence men consultants that forced us to endure their ‘nine-dot puzzle’ during their cheesy ‘team-building’ exercises.

Unlike Austin’s wriggling lines solution, my technique was to draw the dot grid on a chalkboard, then turn the chalk sideways and cover the entire puzzle with a single broad ‘line.’ It got the job done, and it was 100% legal according to the rules presented. The wiser consultants tightened up their remaining material and stopped treating us like first-year MBA aspirants. The obtuse ones … life got worse for them. Much worse.

I bring this up because you’re likely to get a punk like Austin on your payroll someday.  You need to be prepared. Most importantly, you need to accept that you’re partially responsible for the grief that these kids bring you in the office. Yes, they’re being deliberately obnoxious by twisting what you say into something that you absolutely do not want … But that’s because you gave them exploitable instructions in the first place. They can’t job rhetorical grenades at you if you don’t hand them the grenades first.

Display of WWII GrenadesIf you’re going to go to all the trouble to pass them out, it would be rude not to use them.

That’s what imprecise communication causes. Garbled meaning leads to accidents, mistakes, errors, and grief. New Model Army expressed this idea in their song ‘A Liberal Education’ with the mournful lines: ‘You gave us what we asked for / But never what we wanted / We were only children / How could you have been so stupid?’ I first heard that album in 1989, the same year that my military science professors lectured us on the mantra that ‘Careless orders kill soldiers.’

Both thoughts get after the same problem just from different sides of the exchange: NMA presented it from the perspective of the subordinate being unclear; my colonels presented it from the perspective of the superior being unclear. Both use-cases lead to the same undesired result: a communication is misunderstood and things go wrong.

Sometimes, the consequences of unclear communications are relatively tame and give everyone a good laugh. Sometimes, the consequences of unclear communications are tragic and horrifying. Miscommunications have all led to countless unnecessary, wasteful deaths during the Second Iraq War … and the Afghanistan war … and the first Gulf War … and the Vietnam war … Misunderstandings have cost soldiers’ lives all the way back to the world’s first organised fighting forces.

Most of the time (thankfully!), the consequences of unclear communications can be measured in wasted time and labour, and frustration, instead of in injuries or deaths. That’s most often the case in the business world. The worst that happens is a strained professional relationship, as in this summarized example:

BOSS: Make me a nebulously-defined thing that’s unlike anything we normally do

WORKER: Right. Here you go

BOSS: This isn’t what I envisioned at all! I’m angry!

WORKER: Why? I gave you exactly what you asked for

BOSS: I’m angry with myself for being imprecise and with you for not reading my mind

WORKER and BOSS: I will remember and resent this slight until the sun goes cold

Two angry business peopleResponsible leaders own their failures and make corrections. Irresponsible leaders punish subordinates for their own failures.

This isn’t just a common workplace gaffe; it’s a fundamental, built-in vulnerability in humans’ inability function in social settings. It’s a regular trope in literature that goes back centuries. It’s part of who we are. That’s why a snarky troll with a proclivity for misinterpreting orders isn’t just inevitable in the workplace. His type of difficult employee is actually necessary for young leaders’ professional development.

No, really. In the ‘outside the box’ puzzle example that I opened this column with, my Austin has a good relationship with his psyche prof. When he sabotaged her puzzle exercise, she was annoyed and embarrassed, but not mad. To her credit, she learned a valuable lesson about imprecision in written instructions and corrected her teaching material for that exercise to mitigate that exploitable vulnerability. No harm, no foul.

A large part of growing as a leader involves being forced to confront your own weaknesses so that you have no choice but to deal with them. If you have an active mentor who provides timely feedback about your goofs, that’s great! Most leaders don’t. Most of us have to learn from our failures and embarrassments after the damage is done. Often, growth only comes after we’ve made a mistake that got us in trouble, wasted precious time or material, or got our people hurt. Sometimes those mistakes are professionally unrecoverable.

That’s why I believe strongly that you’re lucky if you can hire an irreverent smart&*$ like Austin that will cleverly, mercilessly, and respectfully force us to reconsider our assumptions, speaking style, and failures of imagination. They may annoy us, but they force us to evolve. We have to get better at conceiving, crafting, and delivering instructions if we want to stay one step ahead of our chosen internal nemesis.

Young manager having an argument with his secretary For best results, run your drafts by your designated court jester before taking them public. Their exuberant feedback will help you fix the errors in your message before it reaches a larger audience. 

Punks like my Austin teach us to choose our words carefully and to be precise in our orders. They help us to see the world from a radically different perspective. In the end, that’s what we all need: organisations require diversity of thought and experience in order to reach their full potential. When everyone in an organisation thinks, speaks, and acts alike, the organisation as a whole grows vulnerable. It becomes unaware of its own blind spots and flawed assumptions.

That’s why I prefer to hire a few overly-clever mischief-makers and then give them a certain amount of leeway to confound, frustrate, and surprise me. That’s why you should, too. I’m not suggesting that you tolerate a disruptive nonconformist who wants to tear down your culture. I am saying that you need to hire people that will challenge you to get better in spite of yourself … even if it occasionally stings your ego.

[1] I use term ‘fiendish’ deliberately here. An unworldly intelligent being twisting a well-intentioned mortal’s wish or request to a terrible end in a common trope in myth and legend. Like a djinn dooming a human with a legitimate interpretation of a poorly-worded wish, or a devil interpreting a contract in the worst possible way.


Title Allusions: Justin Sullivan and Stuart Morrow, A Liberal Education (1981 song) from New Model Army’s album Vengeance (1984).

POC is Keil Hubert, keil.hubert@gmail.com

Follow him on Twitter at @keilhubert.

You can buy his books on IT leadershipIT interviewinghorrible bosses and understanding workplace culture 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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