There is a particular kind of failure that doesn’t announce itself as failure until long after the damage is done.
The people involved are smart. The intentions are good. The information available at the time supported the decision. And yet, years, sometimes months later, everyone involved looks back and wonders how a room full of capable people produced an outcome that none of them would choose if they could do it again.
The answer is almost never incompetence. It’s structure.
Decisions don’t happen in a vacuum. They happen inside systems — legal, organizational, social — that have their own logic, their own incentives, and their own momentum. Those systems shape outcomes as much as judgment does. Often more. And most people don’t see the structural problems until they’re already living with the consequences.
This pattern shows up differently depending on where you sit, but the mechanics are remarkably consistent. A decision that looks reasonable at each individual stage accumulates risk over time. Responsibility diffuses across people and roles until nobody owns the question “should we still be doing this?” Incentives misalign in ways that are obvious in hindsight and invisible in the moment. And the loudest voice wins by default, at the most exhausted group’s expense.
What follows isn’t about pointing fingers. It’s about recognizing the structural forces at play before they make the decision for you.
Jump to your situation:
Boards & volunteer governance · Executives & organizations · Job seekers in transition
Volunteer boards face a structural problem that few organizations acknowledge: decisions don’t reset with each new board. They inherit.
When a board makes a significant decision, particularly one that will take years to resolve, the people who made that decision are rarely the ones still sitting in the room when the consequences fully materialize. Terms end. People rotate off. New members arrive with no emotional stake in what came before, but full responsibility for seeing it through.
That creates a dynamic where momentum substitutes for judgment. The question stops being “is this still the right decision?” and becomes “do we give up on what everyone before us committed to?”
Those are not the same question. But they feel the same in the room.
Consider a condominium board that discovers, shortly after taking control from the developer, that critical documents are missing, promised improvements were never completed, and operating budgets were misrepresented during the sales process. They engage an attorney. The attorney uncovers additional issues. The board, acting on legal advice and with broad owner support, decides to pursue litigation for damages.
That decision, at the time it’s made, is reasonable. The harm is real. The case has merit. The owners expect accountability.
What the board doesn’t do, and what almost no board in this position does, is establish clear, documented criteria for re-evaluation. Specific decision points. Pre-committed thresholds that would trigger a formal review of whether continuing is still worth the cost.
Instead, the litigation proceeds. Demand letters are ignored. Discovery drags. Years pass. Legal fees accumulate. The board that filed the lawsuit is no longer the board managing it. New members inherit a decision they didn’t make, along with the political and financial pressure to see it through. Owners who were angry at the developer five years ago are now angry at the board for spending so much money on attorneys.
The incentive structure has quietly shifted. What began as “hold the developer accountable” becomes “we’ve spent too much to walk away now.” Sunk cost logic, the very thing every board member would recognize as irrational in theory, becomes the operating principle in practice.
The structural problem isn’t that the decision was wrong. It’s that there was no mechanism to force re-evaluation before exhaustion, cost, and momentum made the decision irreversible.
In long-running decisions like litigation, governance transitions, or capital projects that span multiple years, responsibility diffuses in a way that makes accountability nearly impossible.
No single board feels they have the standing to reverse a decision made by the collective “we.” The advisory committee that was meant to provide oversight becomes air cover rather than a forcing mechanism for hard questions. The one person willing to name the problem, often someone with a history of skepticism or opposition, gets dismissed as difficult or an iconoclast rather than heard as a canary.
And so the decision continues. Not because each successive board actively chooses it, but because reversing it would require admitting that everyone who came before got it wrong. That’s not a judgment call. It’s a political impossibility.
The guardrail isn’t theoretical governance wisdom. It’s a documented decision framework established at the outset.
If demand letters are ignored for 12 months, the board reconvenes to formally assess whether litigation remains viable. If legal costs exceed a specific threshold relative to potential recovery, a community-wide review process is triggered. If discovery reveals that key documents were destroyed, the board evaluates whether proceeding without that evidence still serves the association’s interests.
These criteria feel excessive when you’re starting. Paranoid, even. Defeatist.
They are none of those things. They are the structural safeguard that prevents momentum from substituting for judgment. They create decision points before the question becomes “do we admit defeat?” instead of “does this meet the criteria we established to test whether this still meets our needs?”
Most boards don’t establish them. And most boards, as a result, end up managing decisions they inherited rather than decisions they would choose.
Corporate environments have a different structural problem: misaligned incentives baked directly into organizational design.
A Chief Operating Officer is measured on stability. Reliable systems. Predictable outcomes. Their job is to keep the lights on, ensure the trains run on time, and prevent operational surprises.
A Chief Strategy Officer is measured on transformation. New markets. Disruptive initiatives. Their job is to identify opportunities that require breaking the current system in order to build the next one.
Put them in a room together to make a decision, and the outcome is often determined not by what’s right for the business, but by who has more organizational capital, who speaks with more authority, or who is willing to fight longer.
That is a structural conflict, not a personality conflict. And it produces predictably bad outcomes when the organization treats it as a collaboration problem instead of an incentive design problem.
In most executive teams, there are always voices that carry more weight. People whose opinions seem more important, whose track record commands deference, or whose communication style simply dominates the room.
There are also quieter, often more thoughtful voices. People who see the risk early, name it tentatively, and then defer when the pushback comes. Not because they were wrong. Because the cost of pushing wasn’t worth it.
A product manager raises concerns about technical debt during a roadmap review, gets firmly overruled by the VP pushing for faster feature delivery, and stops objecting. The issue doesn’t go away, it just stops being discussed.
The group interprets their silence as agreement. It isn’t. It’s exhaustion. Or self-preservation. Or a well-founded belief that challenging the louder voice will mark them as uncooperative, political, or not a team player.
Over time, those quieter voices stop speaking up at all. The dissent that could have prevented a bad decision becomes invisible. And the organization loses the very signal it needed most.
In organizations, responsibility doesn’t just diffuse across people. It diffuses across levels.
The executive team assumes the board, or a dedicated risk function, is tracking the strategic risk, when board members may not be that hands on and risk functions typically manage operational risk.
In contrast, the board assumes the executive team has done the operational diligence. Middle management assumes senior leadership has thought through the implications. And the people closest to the work — the ones who see the problems first — assume someone above them will notice before it’s too late.
Nobody does. Because everyone believed it was someone else’s job.
This is how smart organizations make catastrophically bad decisions with everyone’s fingerprints on them yet nobody’s clearly responsible. The structure made ownership unclear. And when ownership is unclear, accountability becomes impossible.
Pre-committed decision reviews. Role clarity that names conflicts instead of pretending they don’t exist. Processes that force dissent into the open rather than letting it die quietly in the hallway after the meeting ends.
These aren’t soft interventions. They are structural ones. And they work not by changing people’s judgment, but by changing the conditions under which that judgment operates.
Job seekers don’t usually make group decisions. But they operate inside a structure that produces the same dynamic: too many voices, no clear framework for filtering them, and a final decision that represents no coherent point of view.
Everyone has advice. Former colleagues think you should emphasize leadership. Your mentor says to focus on technical depth. The outplacement consultant wants you to lead with metrics. A well-meaning friend insists you’re underselling your creativity. LinkedIn thought leaders have 17 conflicting opinions, all delivered with confidence.
The stakes feel existential. So instead of filtering the advice, you try to incorporate all of it. The result is a self-presentation that sounds like a committee wrote it. Technically accurate. Humanly absent. A Frankenstein narrative that represents no recognizable person.
The structural problem is this: job seekers are operating in a high-vulnerability situation where everyone feels entitled to weigh in. And because the stakes are real — rent, identity, confidence — people defer to volume rather than relevance.
They collect opinions. They treat all voices as equally weighted. And then they either freeze, unable to reconcile the conflicts, or they produce something that tries to please everyone and convinces no one.
This is diffusion of responsibility in a different form. Instead of spreading accountability across a board or a team, it spreads across every person who offered input. If the approach doesn’t work, the job seeker can point to the advice they were given. If it does work, they’re never quite sure which piece of advice actually mattered.
Either way, they’ve abandoned the one source of judgment that actually differentiates them: their own.
The antidote is not ignoring advice. It’s curating it.
That requires knowing yourself well enough to recognize which input fits and which doesn’t. To have a reason for taking advice that’s as clear as your reason for dismissing it. To understand that being authentic doesn’t mean rejecting all external input. It means filtering that input through a coherent sense of self.
People need to listen to their gut. But they also need to analyze what pertains to their situation and what doesn’t. To take what fits and leave the rest. To recognize when they’ve heard enough opinions and it’s time to decide.
That’s not intuition. It’s structure. A decision-making framework that treats advice as input rather than instruction, and recognizes that ultimately, the presentation either represents you or it doesn’t.
Without that framework, the job seeker is just another group making a bad decision. Except in this case, the group is imaginary, and the person paying the price is very real.
Back to top · Jump to conclusion
The board stuck in a decade of litigation. The executive team where the loudest voice wins. The job seeker whose presentation sounds like everyone except themselves.
None of these failures come from lack of intelligence. They come from operating inside systems that have their own momentum, their own blind spots, and their own structural incentives. Systems designed around other priorities entirely.
Pre-committed decision points that force re-evaluation before momentum substitutes for judgment. Role clarity that names conflicts instead of pretending they don’t exist. Processes that surface dissent instead of allowing it to die quietly. Frameworks that help individuals filter input rather than deferring to volume.
And they work not by making people smarter or better-intentioned — most people already are — but by changing the conditions under which judgment operates.
The question is not whether smart, well-intentioned people can make bad decisions.
They can. They do. Regularly.
The question is whether the structure around them makes those bad decisions harder to sustain. Or easier to inherit, defend, and repeat until the damage is undeniable.
