Dear Executive
Dear Executive, how do you manage your Appreciative System?
Dear Executive,
how do you manage your Appreciative System?
When you opened your inbox this morning, what grabbed you first, the legal risk memo or the management accounts? Sir Geoffrey Vickers shines a light: That instinct wasn’t random; it came from your appreciative system, that silent personal algorithm that decides what counts as signal, what gets blurred, and what fires action.
When last did you inspect its code e.g., what information did you let go in the last million-rand conversation, what did you park as ‘noise’ and why did it feel irrelevant at the time? Or, if you replay yesterday’s meeting, can you spot the moment “fair” or “strategic” slipped through unchallenged? Which trigger phrase, “speed to market,” “people first,” “ESG”, flips you from analysis to autopilot?
Make the effort and check yourself: record your next big decision on voice-note. Twenty-four hours later, highlight the numbers you ignored and the values you assumed. That gap is your system showing its hand. Do this for any important strategic decision you may want to take.
Now go one step further: pivot your lens and judge the same issue one year out instead of this quarter. Which facts rise, which sink? Know this: strategy rides on those shifts.
We cannot escape our appreciative system, but running an unexamined appreciative system is risky. It is like budgeting in invisible ink, it looks fine until the audit light hits.
Dear Executive, do you know what the builder means when she shouts “Bricks”?
Dear Executive,
do you know what the builder means when she shouts “Bricks”?
On a construction site a mason calls out ‘bricks. There are no adjectives, no verbs, and yet everyone moves. Pallets slide, trowels rise. One noun has issued an order, set a priority, pushed the work forward. Bricks arrive. Wittgenstein, the language philosopher, would call that a language game: meaning of the word, lives in the action, not the dictionary.
Think of your Exco meetings: which words do that in your meeting? “Synergy,” “agile,” “rightsizing”, are they triggers for action or polite background noise? Wittgenstein’s language-game insight still bites: a word’s meaning sits in what it lets us do together, not in the syllables themselves i.e., if we understand the game and its rules.
When finance says “optimise,” does IT hear “cut”? When you promise “transform,” do customers brace for downtime? How often does your communication explain the rules before the first move? Pause a bit. Instead of what are we saying, ask what move are we making? Are we informing, requesting, warning, inviting? Different game, different rules.
Consider your next memo or mail: If you removed the logos and titles, even the verbs, would every reader still know who must do what next, like the builder’s single shout ‘bricks’ does?
Clarity often feels blunt; jargon feels clever. Words pour the concrete of strategy. Choose them like materials. If not, your people may wait for instructions while you admire the diction.
Dear Executive, have you considered CERTAINTY as the enemy?
Dear Executive,
Have you ever walked into a meeting where someone—maybe even you—was so certain about their position that the conversation lost its spark?
The questions stopped, the energy dropped, and people either nodded along or checked out completely. When leaders hold too tightly to certainty, what gets lost? Does innovation stall? Do differing perspectives go unheard? Do we, without realising it, create environments where learning takes a backseat to being right?
Certainty feels powerful—it gives us confidence, clarity, and direction. But what if it also closes us off? What if the best ideas, the ones that truly transform businesses, emerge from admitting we don’t have all the answers?
Perhaps leadership isn’t about having certainty, but about holding space for curiosity- for self and others. Maybe the real strength is in staying open.
Dear Executive, do you know the story of the Camel's Nose?
Dear Executive
Executives often find themselves navigating treacherous slopes, don't they? Think of your strategic decisions, corporate policies, letting a minor policy slip slide to hit a deadline or subtle shifts in organisational culture. We sometimes do seemingly innocent exceptions or small compromises that lead to unintended and sometimes disruptive outcomes.
The fable of the camel’s nose, charmingly told by poet Lydia Howard Sigourney, captures precisely this scenario. Imagine: A camel requests merely to warm its cold nose inside a worker's shop. Seeing no harm, the worker allows it. But soon, the camel’s head follows, then its neck, and eventually its entire ungainly body, until there's no space left for the rightful occupant.
Reflecting on one’s leadership experience—has a small concession ever gradually expanded into something far greater and far less manageable? How can we recognise these "camel’s noses" in our own corporate tent?
Consider the wisdom embedded in this seemingly simple tale. It challenges an executive, to ask: What small allowances are you making today, and are you prepared for their potential consequences tomorrow? How does one hold firm to keep the whole camel out? The choices we make are the moments that shape our legacy as leaders.
Dear Executive, do you think you own Hilbert’s Hotel?
Dear Executive,
Do you think you own Hilbert’s Hotel?
There’s a thought experiment in mathematics called the Infinite Hotel. A hotel with an infinite number of rooms, all occupied, yet it can still accommodate more guests. Just shift everyone one room over.
The paradox reveals something we executives often overlook: in theory, capacity can be endless. In practice, it never is. We celebrate scaling. platforms, ecosystems, digital models, all promise exponential growth. But we ought to ask the harder question: Where does it start to break?
People don’t scale like servers. Culture doesn’t replicate like code. Trust, leadership, attention, these don’t expand infinitely. They stretch. Then strain. It’s seductive to believe that if something works at 10x, it will work at 100x. But at some point, growth becomes noise, complexity becomes chaos, and a strategy that worked at one scale begins to quietly fail at another.
So, what’s this all about? Well, firstly, it isn’t to fear scale. Then what? It’s to understand its structure, and respect its limits. Before we open more rooms, we need to ask: Do we have the architecture (human, cultural, strategic) to hold what we’re building?
Infinity is an idea. Leadership deals in realities.
Dear Executive, are you misreading the odds?
Dear Executive,
Are you misreading the odds?
Imagine you’re offered a second chance in a high-stakes decision — do you switch paths or stay put? The Monty Hall ( remember the show?) paradox says: switching is the smarter bet. Yet most people stay. Why? Because the mind loves certainty, even when it’s wrong!
In business, we mostly start with partial information. Then new data arrives. A merger becomes a botch. A deal falls through. A partner (surprisingly) reveals more information. A market shifts. And now the inevitable happens, you must choose: stick or switch?
Here’s the possible trap, though — your original choice still biases your judgment. Even when better options open up, your gut whispers, “Stay loyal to the first call.” Now, is that strategic discipline — or cognitive inertia?
The business world confronts us as executives with this challenge: learn to update your probabilities, not your justifications. New information should reframe your odds, not harden your position.
If you find the time, consider reflecting on this question: Am I holding firm because it’s right, or because it’s familiar? And if the odds have changed, why haven’t I?
And while you are at it, consider the possibility that strategy isn’t about being right first. It’s about being more right as you progress on the strategic path.
Dear Executive, are you still paying for something you've already paid for?
Dear Executive,
Are you still paying for something you've already paid for?
The sunk cost fallacy is subtle. It doesn't shout. It whispers: “You've invested too much to stop now.” You know the story — the project that's faltering, the partnership that's grown stale, the strategy that no longer fits, the JV that no longer offers value. And yet, the instinct is to persist.
Why? Because of the time, money, and effort already spent.
But here’s the rub: those costs are already sunk. They no longer belong in the equation. We are indeed tempted to think, “We’ve come too far to turn back now.” But is that conviction or emotional bookkeeping? It is an important question because there is a critical difference: Smart persistence is forward-looking.
The real question is sharper: Would you choose this again today, knowing what you now know? Persistence, we’re told, is a virtue. But so is discernment. The best entrepreneurs don’t keep going because they’ve invested a lot; they keep going because, despite the cost, they still see future value. There comes a time not to push forward, but to stop, to exit, to reallocate. The cost of quitting is measurable. The cost of clinging is often hidden — until it isn’t.
Upon reflection: is leadership just about backing what you've started or is it also about knowing when the future demands a different decision?
Dear Executive, are you suffering from suvivorship bias?
Dear Executive,
Are you suffering from the Survivorship Bias?
Are you building your strategy only by studying the winners? The unicorns, the legends, the “we made it” stories? What if what you don’t see is more important than what you do?
Survivorship bias occurs when we draw lessons from those who made it, while ignoring the silent graveyard of those who didn’t. That impressive product launch? Nine others failed quietly. That bold leadership move? Perhaps it rode a wave, not wisdom. It might’ve succeeded because of the market, not the method.
How often do you ask, “What’s missing from this picture?” “What are we not seeing?” What’s been edited out of your boardroom or Exco conversations by sheer absence? Survivorship bias whispers, “Look at the winners, they’ll show you the way.” We quote them. We emulate them. We reward them. But what’s been left out? Who failed? And why?
There may be value in asking, before you greenlight the next step: Is our strategy shaped by truth (evidence) or by the illusion of evidence? Great leaders don’t just study success. They examine failures.
If we are to lead Africa toward a sustainable, just, and wise future, we must learn not only from the victors, but from the vanished. Let’s interrogate the silence.
Dear Executive, are you still at the helm of Theseus ship?
Dear Executive,
You might know the riddle of Theseus’ ship—a vessel where every plank, sail, and nail are replaced over time until nothing original remains. Is it still the same ship? It’s not just a philosopher’s game; it’s a mirror to your world. Every leader faces a version of the Ship of Theseus paradox. You’re making calls every day—new strategies, fresh tech, shifting teams—each move swapping out another piece of your organisation’s framework.
But here’s the kicker: have you ever paused to ask if this company, after all those changes, is still the one you signed up to lead? Or has it morphed into something else entirely? What anchors its identity—the people who cycle through, the products that pivot, the values that flex with the market, or something less tangible?
You’re at the helm, steering through relentless transformation. Change is non-negotiable if you want to keep sailing. Yet are you safeguarding its soul, or crafting a new beast? How do you preserve the spirit that made your enterprise worth building in the first place? How do you keep the mission sharp when the parts keep changing?
Leadership isn’t just riding the waves of change—it’s ensuring that, through every shift, the ship still feels like yours, its purpose unmistakable.
What’s your compass here?
Dear Executive, how does one speak of the sea to the frog that has never left its pond?
Dear Executive,
How does one speak of the sea to the frog that has never left its pond?
Can you imagine explaining the vast, interconnected digital world to someone who's only known the confines of traditional business. When you cast your eyes over your business and your workforce, how do you foresee preparing yourself and them for a future where work knows no physical boundaries?
As executive leaders, shouldn't we ask ourselves, are we ready to embrace digital literacy, or are we stuck in our comfort zones? (Remember Murphy’s Third Military Law?)
With AI reshaping industries, how can you foster a culture that not only accepts but thrives on change which occurs at a relentless pace?
Consider reflecting on this: Should you and your team of leaders be cultivating the emotional intelligence needed to lead diverse, remote teams? In our current understanding of a digitally transformed world, the businesses that will thrive are those that not only adopt new technologies but also transform their leadership approach, skill sets, and organisational culture.
The sea of digital transformation is vast; it seems a leadership imperative to ensure we're not just frogs in a pond but explorers of this expansive ocean.
Dear Executive, are you caught up in the hamlet doctrine?
Dear Executive,
Are you caught up in the Hamlet Doctrine of knowing too much and doing nothing?
In Shakespeare’s Hamlet, the prince learns the truth early—his family’s corruption, the rotten political order—yet he’s paralysed. Unlike Oedipus, who acts first and uncovers reality later, Hamlet’s knowledge drowns him in thought, not action. It’s a curse: insight breeds nausea, melancholy, and inaction.
Sound familiar? You’re flooded with data, I know—endless reports, analytics, data streams, expert opinions, forecasts. Knowledge is power, but it can also trap you in “analysis paralysis.” Overthinking stalls decisions; fear of the wrong move stops all moves. Like Hamlet, one might feel stuck, watching opportunities slip as thought and action pull apart. It’s a modern tragedy—too much information, too little resolve.
How does one escape this modern-day trap?
Recognise the pattern. Balance reflection with bold steps. Embrace strategic experimentation. Simplify the flow of information to avoid drowning in detail that add no real value. Hamlet mused, “There is nothing either good or bad but thinking makes it so.” Avoid overthinking. It rots your potential. Leaders act, learn, adapt. The gap between thought and action narrows when you dare to move.
Dear Executive, do you deal with wicked messes?
Dear Executive,
Do you deal with Wicked Messes?
Wicked messes are those complex problems that seem impossible to solve, like our healthcare system. Well, tackling these requires more than just knowledge. It’s about HOW you think and your state of mind.
Firstly, you need a solid grasp of the issue, think critically, evaluate information, and apply different models. It doesn’t end here. Your psychology shapes how you solve (dissolve?) problems. You surely heard about the “Parent, Adult, Child” model? The “Parent’ in you sticks to the rules and can be rigid. The “Child’ in you acts on impulse. The “Adult’ in you stays rational and objective- aim for that yet give your “Parent” and “Child” a place and a voice.
Next consider this: Are you a “Secure” or “Insecure” adult? Secure adults tend to embrace new ideas and thrive in uncertainty. Insecure ones seem to resist change and stumble with ambiguity.
Would you consider, when handling wicked messes, to lead by mixing deep knowledge with self-awareness? Although not a silver bullet: understand the problem but also know yourself. Stay logical, stay open, leading your team to unravel those wicked messes.
Dear Executive, are you familiar with Murphy’s third military law?
Dear Executive,
Are you familiar with Murphy’s Third Military Law? It warns that "the most dangerous thing in the combat zone is an officer with a map." Strange? Maybe.
But in leadership, this rings true. Plans and strategies crafted from a distance often miss the terrain’s real obstacles. How often do we stick to a strategy, even as conditions shift? And what insights are lost between decision-makers and those on the ground?
The best-laid strategies can crumble in execution. The lesson? Humility matters. Robust data must be paired with frontline intelligence. After all, Murphy’s Law reminds us: if anything can go wrong, it probably will. When the map no longer matches the territory—how ready are you to adapt?
Dear Executive, have you consulted the Philosopher’s Stone on moral character?
Dear Executive,
Have you consulted the Philosopher’s Stone on Moral Character?
When challenges arise a behavioural choice arises: do I act from genuine conviction or a sense of obligation? For centuries, thinkers like Aristotle, Confucius, and Plato pondered how our actions reflect our virtues—or expose our failings.
Their timeless question remains: Do you truly live what you believe in your core? It’s not about perfection; it’s about honesty with yourself and consistency in your daily interactions. Their core premise is that the alignment of our behaviour with our core values, like the philosopher’s Stone, turn the ‘base metal’ (lead) of our human nature into a more refined and elevated form (gold).
Should you have time to reflect on your decisions this week—did they align with the ideals and values you profess? Those you find falling short, what small step could you take toward authenticity? It seems that true leadership emerges when your outward choices mirror your inner values.
Dear Executive, allow me to introduce you to the masked-man-fallacy
When was the last time you funded an idea because the name felt cutting-edge rather than the evidence? We fall for it ever so often i.e., the masked-man fallacy. Just rename a dusty “Legacy System Upgrade” to “Quantum-Ready Core,” and watch the signatures flow. Same code, shinier mask. Meanwhile a modest-looking “Process Tidy-Up” gasps for airtime, though its ROI glows.
Would you consider some reflective questions e.g., which projects survive on brand halo instead of hard data? Strip logos, anonymise authors, and ask: Would I still approve this if I had no clue who built it? Or the language trap: how many initiatives are “digital transformation” in marketing decks but plain “core plumbing” in the server room, and yet treated as two budgets?
Leibniz smile, because the masked man thrives on unchallenged vocabulary. One way of ripping of the mask is by backing every decision with measurable attributes (cost to deliver, resilience gained, risks burned down) nothing your brand manager can Photoshop.
As executives we frequently need to dust off the question of how many million-rand bets in our pipeline are really wagers on adjectives? And perhaps, if we unmask the work, one might discover the quiet superstar already hidden in plain sight.
Dear Executive, allow me to introduce you to Cipolla’s ‘stupidity’
Cipolla offered five “laws” that explain why stupidity is a systemic force in human conduct themselves. Question: What if tomorrow’s board pack misbehaves because people do?
Carlo Cipolla’s “laws of stupidity” insist that value-destroyers lurk in every meeting, outnumbering your instincts. His First Law: we always undervalue that headcount. His Fourth: we’ll repeat the error next quarter. The result? Projects that burn both shareholder equity and team morale while enriching no one, yet we still call them “strategic bets.”
What proposals are on your agenda? Which proposals presume rational actors once the lights dim? Who’s counting on goodwill instead of guardrails? Before you sign shouldn’t you ask “If this implodes in twelve months, what killed it?” If the room falls silent, you ought to hear alarm bells. Have you considered trip-wires, tied to cash burn and not heroics or excuses?
Do you have at least one empowered Sceptic whose KPI is to break the idea before reality does. Titles don’t immunise; dissent is cheap insurance.
And your culture? When was the last time someone told you, “This plan is foolish,” and kept their bonus? If that feels unlikely, consider the possibility that you’ve designed an echo chamber where Cipolla’s laws run free.
If systemic stupidity is a statistical certainty, is your organisation engineered to catch it early or to politely fund it?
