How Systems Reward the Wrong People And Why Unfixing This Is Harder Than You Think

The Wrong People Keep Winning

We know something is broken when organisations reward:

• Those with the loudest voices, often elevated for historical or political reasons, not those with the clearest insight
• Those who decorate problems, not those who solve them
• Those who scale dysfunction, not those who fix root causes

This is not a coincidence. It is systemic.

How It Starts – Proximity over Competence

For decades, many organisations have promoted individuals not for their competence, but for their proximity to power. A familiar example is the loyal lieutenant who never questions leadership decisions, always present in every meeting, always available to absorb blame or repeat the official narrative. Over time, such figures ascend not for their insight, but for their utility as echo chambers. Being in the right room at the right time matters more than building the right thing. This has created a self-replicating elite of visibility over substance.

Fear-driven development exacerbates the problem. Individuals who retain bottlenecks, hoarding knowledge or maintaining critical legacy systems, become indispensable by default. Rather than removing the obstacle, leadership rewards the obstacle for its obstructive value.

Hiring practices often follow suit. Instead of seeking talent that challenges the status quo or elevates the team, managers gravitate towards candidates who pose no threat. Safer, quieter, more compliant. In the name of harmony, organisations dilute their own potential.

And underpinning it all is a quiet, pervasive denial of reality. The truth is hard. It demands rigour. It makes people uncomfortable. And so the system compensates by celebrating the performative and punishing the corrective.

These are not isolated flaws. They form an ecosystem of dysfunction, resilient, self-sustaining, and hostile to change. This ecosystem is rarely deliberate. It emerges gradually, as well-intended shortcuts, political calculations, and fear-based incentives accumulate. Over time, these patterns harden into the system's default state.

The Visible Damage – What Dysfunction Looks Like

This dysfunction manifests in visible and measurable symptoms:

• Inconsistent strategy and shifting priorities
• Ad-hoc work that ignores long-term impact
• Lack of alignment across teams and leadership
• Poor employee satisfaction and retention metrics
• Eroded trust in company decisions and direction
• A cultural drift toward entitlement, where engineers, or worse entire teams, behave like spoiled children, demanding rewards while resisting feedback or responsibility

When these symptoms persist, they do not only hinder performance. They compound decay. They mask the real rot, ensuring the cycle repeats.

How It Persists – Comfort, Theatre, and Inversion

These symptoms are not random. They are consequences of deeper systemic patterns that reward conformity over courage.

The stories of WeWork and Theranos offer cautionary tales. In both cases, narrative overpowered scrutiny. At WeWork, the charismatic founder was endlessly rewarded for vision while ignoring operational and financial reality. Employees who questioned direction were sidelined, as the organisation chose theatre over accountability.

Theranos took this even further. Engineers and scientists who spoke up were punished or removed, while the illusion of breakthrough innovation persisted. In both companies, the system systematically rewarded compliance and punished integrity, until collapse made the truth undeniable.

At the heart of this dysfunction is a web of well-intended mechanisms that have been slowly corrupted. Incentive structures reward what is easy to measure, not what matters. Visibility trumps value. Metrics become a proxy for meaning, and soon the appearance of productivity outpaces real contribution.

Misinterpretations of psychological safety add another layer. Rather than fostering environments where truth can be spoken and hard questions asked, many teams begin to interpret safety as comfort. Discomfort becomes a risk, not a signal. Those who challenge assumptions or raise inconvenient truths are labelled as disruptive, and quietly excluded.

Performance theatre thrives in such conditions. Effort is replaced by optics. Rituals are mistaken for progress. Stand-ups that merely cycle status updates, retrospectives that never question leadership decisions, and demos built for applause instead of feedback, all become theatre in place of meaningful iteration. Meeting culture expands, retros lose their teeth, and leadership celebrates the rhythm of the process without ever questioning its effectiveness. The game becomes acting like a team, not delivering as one.

Meanwhile, value inversion sets in. The system begins to elevate the narrator over the builder, the diplomat over the doer, the adapter over the challenger. People learn to play roles that are socially reinforced but operationally hollow.

This is how systems reward the wrong people, not through conspiracy, but through slow erosion. And unfixing it requires not just courage, but a fundamental reframing of what we choose to see, measure, and value.

The Way Out – Optionality and Broken Windows

The first step toward healing is restoring structural consistency. Teams must be able to measure and own their process. Not as an illusion of autonomy, but as a real, protected space for decision-making. This means clear decision rights, consistent guardrails, and the confidence that good decisions will not be undone by political winds or performative escalations. It is a space where engineers and leaders alike know the rules of the game, and trust they will not change mid-play. When consistency anchors the work, people can act without fear of political retaliation, escalation, or becoming collateral damage in someone else's performance theatre.

If systems reward the wrong people, it is because they lack the structural conditions to reward courage, only compliance. To reverse this spiral, two principles must be reintroduced:

1. Restore Optionality
Drawing on Nassim Nicholas Taleb's insights from Antifragile, rationality is not about certainty of outcome, but availability of principled options. When truth-telling, dissent, or action carry too much risk, no rational actor will attempt them. Restoring optionality means creating roles, paths, and systems where integrity is viable, not suicidal.

If the only rational path is silence, then the system is irrational by design.

2. Fix the Broken Windows
The Broken Windows Theory reminds us that visible neglect leads to deeper decay. In organisational terms, ignoring small acts of dysfunction, or failing to recognise small acts of rigour, sets the tone. The window does not have to be structural. It can be as subtle as who gets praised in a meeting, or who gets sidelined after raising the alarm.

Rewarding integrity at the micro level is how trust scales. Do not wait for a full reorganisation. Start by noticing who fixes the small things.

The system will not change because of slogans. It will change because someone, perhaps just one person, decided to act without waiting for permission.

Until we acknowledge the mechanisms, not just the symptoms, we will continue to optimise the wrong behaviours, and call it success.