When an organization grows unhealthily — too fast, for bad reasons, or through bad recruitment — it will also shrink unhealthily. When it grows it’s bold and confused. When it shrinks it’s scared and nasty. The asymmetry matters: growth mistakes are forgiven because the tide is rising, but shrinkage exposes every structural weakness simultaneously and adds fear to the mix.
Simple Picture
A plant in a small pot grows until its roots fill every available space. It becomes rootbound — still alive, still green on top, but unable to grow because every path is already occupied by existing root structure. Organizations do the same thing: they fill their container (market, mandate, team size) and then ossify. New growth cannot find space because old structure has claimed everything. The organization appears stable but has traded adaptive fitness for the illusion of security. It is better to be strong than secure, because you cannot be secure.
The Entropic Preference Stack
Hierarchical and other kinds of entropic organizations always favor solutions that survive within entropic organizations.
The preference stack of organizational entropy:
- Easy over simple — easy is what feels comfortable; simple is what works but may require hard choices. Entropic organizations choose the comfortable path and add complexity to manage the consequences.
- Complex over difficult — complex solutions create job security for the people who understand them; difficult solutions require actual skill but are transparent once solved.
- Responsibility-dilution over empowerment — distributing blame across committees and processes protects individuals; empowering people exposes them to accountability for outcomes. This is the kernel of CYA culture — protection from outcomes is the load-bearing benefit, and the rest of the bureaucracy is scaffolding to deliver it.
- Accountability over learning — tracking who failed is safer than asking what was learned. Learning requires admitting ignorance; accountability only requires assigning fault.
- Shock therapy over culture-nurturing — reorganizations, new methodologies, and consultant-driven transformations feel decisive; slow cultural work feels like doing nothing.
The solution pollution frame names the end state: the entropic organization does not fail because it lacks solutions — it fails because it cannot stop solutioning. The culture change insight is embedded here: entropic organizations will always worry about the development team’s ability to deliver by a given date, never about its ability to find the right solution. The deadline is legible; the quality of the solution is not. The legibility bias ensures that the measurable concern always dominates the important one.
The Fog and the Silence
When no one knows who the good or bad contributors are, this fog of war creates the negative form of office politics. There are major incentives toward social manipulation because social capital is the only currency that trades in the dark.
The most dangerous symptom: allowing reported issues to result in zero action. This is the quickest way to convert enthusiastic employees into clock-in-clock-out workers. Most employees, especially engineers, want to improve the company and themselves — until you prove that their thoughts do not matter.
Usually an outstanding problem is already known by the staff. Often they have tried to make leadership aware. But the issue gets prioritized into nothingness, or filtered into white noise by the chain of command. Worst case: someone raises it directly to a senior decision-maker, and the intent to ignore is made clear. This is simple sabotage in its subtlest form — not active destruction but passive suffocation of feedback.
As a manager, you can gauge whether engineers are healthy by checking if they are comfortable giving constructive feedback directly. Management might see an increase in reported problems during development, but they’ll also see an increase in resolutions — instead of seeing fewer but critical issues that fester unresolved. The feedback pipe is open or it is not; there is no middle ground.
The evaporation follows naturally. The most talented engineers are the least willing to work in an environment where their feedback disappears into nothingness. They leave. The residue is grateful to have a job, makes fewer demands, and reinforces the very culture that drove the talent out.
Engineering in Entropic Systems
Will tend to go all out attacking the first problem rather than thinking through and avoiding them. This is the engineering version of the entropic preference for easy over simple: jumping to implementation feels productive, but premature action on the wrong problem is worse than delay.
Without requirements or design, programming is the art of adding bugs to an empty text file.
The more you learn about your problem, the more you understand that whatever you wrote won’t solve the problem in the long run.
Incompetence is fiercely gregarious. Raw ideas transfer more easily through untrained minds. An inexperienced team develops an echo chamber where nobody has the frame of reference to challenge bad assumptions. The Expert Beginner dynamic at the team level: confidence without competence, reinforced by the absence of anyone skilled enough to provide contrast.
Instead of forcing underskilled engineers to attempt something above their level, break the project into smaller systems — possibly cutting features in the process. Overtaxing your engineering effort is a surefire way to end up with hard-to-maintain work. It’s often better to lose battles than to staff desperately and win desperate battles at all costs. The Apple approach: wait for the right person rather than fill the seat with whoever is available.
A high-level engineer will often look outside the code to diagnose issues with it. When many moving parts are involved, knowing the background of all parties can be illuminating. If called in to fix engineering issues, seek out the people who are clearly disgruntled — they are the ones who have been seeing the problem clearly and being ignored. 95% of time is usually spent identifying the problem, 4% involves fixing it, and 1% is telling everyone it’s been fixed.
Process vs Judgment
In ambiguous situations, process is not a replacement for human judgment. Human trust is superior to blind adherence to dogma. The mark of a born bureaucrat is figuring out how to do something before figuring out the details of the what, and never getting to the why.
Teams don’t self-organize unless you organize them to do so. The leader-leader model is not spontaneous — it requires deliberate structural choices that create the conditions for distributed initiative. Simply announcing “we’re agile now” or “teams are empowered” without changing the actual power dynamics produces neither agility nor empowerment.
Get everyone to independently have ideas before a debate instead of “collaboratively” creating one through committee. The Surowiecki conditions for collective intelligence require independence — and independence in organizations must be structurally enforced, because the natural gravitational pull is toward conformity and deference.
Dimwit / Midwit / Better Take
The dimwit take is “toxic workplaces are caused by toxic people — remove the bad actors and the culture improves.”
The midwit take is “culture is set from the top — leadership needs to model the right values.”
The better take is that entropic organizations are not caused by bad leadership or bad people but by structural incentives that reward entropy and punish clarity. When feedback is filtered into nothingness, when issues are prioritized into oblivion, when process substitutes for judgment — these are not failures of character. They are the natural equilibrium of any system where the consequences of inaction are invisible and the consequences of action are visible. The person who raises an uncomfortable truth gets labeled a troublemaker; the person who stays quiet gets labeled a team player. The system selects for silence, and silence selects for entropy.
Main Payoff
The constraint in an entropic organization is not talent, process, or technology. It is the feedback loop. Every other dysfunction — bad code, wrong priorities, talent flight, political maneuvering — is downstream of a broken feedback mechanism. The organization that listens to its disgruntled engineers (they are the canaries) and acts on uncomfortable truths will outperform the one with better talent and better tooling but broken feedback. The rage that propels you in a dysfunctional environment is useful — but intrinsically tiring. It will take control the moment you are too tired to hold it. Stop well before.
Always remember: to argue and to win is to break down the reality of the person you are arguing against. It is painful to lose your reality. So be kind, even if you are right. Always be the humble explorer.
References:
- Workplace retrospective, personal experience
- Louis Srygley, “Without requirements or design, programming is the art of adding bugs to an empty text file”