A reader sent me detailed feedback on Part 3. The critique was thoughtful, well-reasoned, and largely correct.
The core argument: the Four Pillars framework assumes rational actors, aligned incentives, functional governance, and time to evaluate decisions properly. Most organizations don’t have those things. The framework is a good thinking lens but a weak operating model in environments where politics, time pressure, and misaligned incentives dominate.
I’m not going to argue with that. I’m going to dig into it.
Because here’s what the critique surfaced: the framework has preconditions. When those preconditions exist, the pillars work. When they don’t, the framework becomes a slide deck that everyone nods at and nobody follows.
This piece is about those preconditions. What they are, how to recognize when they’re missing, and what to do when you find yourself in an organization that won’t build them.
There’s hope in this. But we have to walk through the darkness first.
The Preconditions
Here’s something about leadership decisions that doesn’t get talked about enough: they compound.
The further up the organization you climb, the broader the horizons. Small changes have large impacts. A tool choice at the top affects every team below. A process decision in the executive suite shapes how hundreds of people spend their days. A cultural norm modeled by leadership becomes the water everyone swims in.
This is why the preconditions matter so much. At the individual contributor level, a bad decision affects one project. At the team lead level, it affects one team. At the director level, it affects a department. At the executive level, it affects the entire organization.
Failure to make decisions at the top doesn’t create a vacuum. It creates chaos. Teams make their own calls. Those calls conflict. The conflicts multiply. Small divergences become massive fragmentation. And by the time leadership notices, the cost of correction is enormous.
The Four Pillars assume certain things are already true at the altitudes where decisions compound most. Let me name them directly.
Servant leadership.
The framework assumes leaders who ask “how do I serve my team and my customers?” rather than “how do I hit my numbers and advance my career?” Leaders who absorb ambiguity so their teams can operate with clarity. Leaders who make the hard calls because that’s their job, not because it makes them look good.
Part 1 of this series argued that leadership failure is the root of organizational dysfunction. That’s still true. But saying “leadership should be better” doesn’t help the reader stuck under leadership that isn’t.
Psychological safety.
The framework assumes people can speak honestly without fear. That when an engineer says “this tool is making my job harder,” leadership can distinguish legitimate concern from comfort zone protection. That feedback flows upward without being punished, and decisions get revisited when evidence warrants it.
Without psychological safety, Pillar One gets weaponized. “Impact on the individual” becomes a shield for resistance to any change. Or worse, people stop giving honest feedback entirely, and leadership loses the signal they need to make good decisions.
Customer obsession as actual priority.
The framework assumes the organization genuinely puts customers first. Not “customer first” on a poster while quarterly revenue actually drives every decision. Real customer obsession, where the question “how does this serve the people we exist to serve?” carries weight in every discussion.
Without this, Pillar Two becomes decoration. Customer impact gets mentioned in the slide deck and ignored in the decision. Short-term budget and timeline pressures win because they have numbers attached, while customer experience remains abstract.
Willingness to measure honestly.
The framework assumes the organization will define success criteria upfront, instrument the metrics, and actually look at the results. That leadership wants to know if decisions are working, even when the answer is uncomfortable.
Without this, Pillar Four dies quietly. Metrics get defined but never instrumented. Results get measured but never reviewed. Or worse, people game the metrics, optimizing for the number instead of the outcome the number was supposed to represent.
These are the preconditions. When they exist, even imperfectly, the framework has something to build on. Without them, you’re pushing rope uphill.
The question is: how do you know which situation you’re in?
The Diagnostic
I’m a problem solver. Everything is a puzzle for me to put together or solve. I’ve spent twenty years in technology breaking down complex systems, finding the failure points, building solutions.
This is no different. Your organization is a system. It has inputs, outputs, and failure modes. Before you can fix it, or decide it can’t be fixed, you need to diagnose it.
Not every dysfunctional organization is hopeless. Some are imperfect but improvable. Others are structurally incapable of change.
The difference matters. It determines whether you invest energy trying to build the preconditions or recognize that your efforts will be absorbed without effect.
Here’s the distinction I’ve learned to make: organizations that know they’re imperfect can improve. Organizations that believe they’ve already figured it out cannot.
This sounds simple. It’s not. Most organizations claim to value feedback, continuous improvement, learning from mistakes. The words are everywhere. The question is whether the behavior matches.
Signs you’re in an improvable environment:
Leadership changes their mind when presented with evidence. Not easily, not always, but sometimes. You’ve seen a decision get reversed because data showed it wasn’t working. You’ve seen someone admit they were wrong without it becoming a career-limiting move.
Feedback occasionally travels upward. Not every time. Not without friction. But there’s at least a path. Someone in the organization has successfully influenced a decision by raising concerns.
Failures get examined, not just punished. When something goes wrong, there’s genuine curiosity about what happened. Postmortems exist and occasionally produce real changes.
Signs you’re in an environment that won’t change:
Feedback is punished, explicitly or implicitly. “Opportunity for improvement” meetings that are actually warnings. People who raised concerns finding themselves sidelined. A pattern of messengers getting shot.
The same problems recur without acknowledgment. You’ve watched the organization make the same mistake multiple times. Each time, it’s treated as new. Nobody connects the pattern because connecting the pattern would require admitting the pattern exists.
Relationships trump outcomes consistently. Decisions get made based on who’s in the room, not what’s right. The inner circle determines what gets approved. Being right matters less than being connected.
Leadership is defensive about the organization itself. Any suggestion that something could be better gets reframed as an attack. “That’s not how we do things here” ends conversations instead of starting them.
If you’re in an improvable environment, the rest of this post is about how to build the preconditions within your sphere of influence.
If you’re in an environment that won’t change, the rest of this post is about recognizing that clearly and making good decisions for yourself.
Both paths have hope. But they’re different paths.
The Environment That Won’t Change
I need to tell you about my worst professional experience.
I won’t name the company or the people involved. That’s not the point. The point is what I learned about recognizing an unsalvageable situation.
I took the role because it looked like a career opportunity. Platform architecture, establishing standards, building frameworks from my experience. I was told this work mattered, that it was important, that I’d have the latitude to make real change.
The red flags were there during the hiring process. Leadership dysfunction that was visible even from the outside. Communication that was confusing when it existed at all. I saw these things and talked myself past them. Better opportunity. Career growth. The usual justifications.
What I found was an organization built on acquisitions that had never been integrated. Tool sprawl and process fragmentation everywhere. Every step revealed something new that didn’t fit, didn’t connect, didn’t work. Walking through a dark room covered in Legos, every step bringing sharp pain at some new discovery.
Could I have fixed this? Technically, yes. The problems were solvable. Was I given the opportunity? No.
The reality was a leadership team that was blind to anything but relationship incentives. Value was measured by loyalty, not outcomes. My role wasn’t to build something better. It was to be an echo chamber, validating decisions that had already been made by people who had no interest in feedback.
Every attempt to surface concerns resulted in “opportunity for improvement” meetings. Code for: sit in the corner and do what you’re told. The organizational mafia was firmly established. If you weren’t in it, you weren’t heard. Not because your ideas were wrong, but because you weren’t the right person to have ideas.
I left quickly. It was the right decision.
Here’s what that experience taught me: some environments cannot support good work. Not because the problems are too hard, but because the organization has no interest in solving them. The dysfunction isn’t a bug. It’s the operating system.
Recognizing this isn’t failure. It’s clarity.
Building Within Your Sphere
If you’re in an improvable environment, you have more agency than you think.
You probably can’t fix leadership overnight. You can’t mandate psychological safety across the organization. You can’t force customer obsession into the culture by sheer will.
But you can build these things within your reach. And that’s where change actually starts.
Start with your team.
When I led a team at 10th Magnitude, the managed services company where I helped build the practice from the ground up, we lacked any structure in tooling and process. Architects, developers, and engineers all gravitated toward what was comfortable for them. The result was discontinuity on every front.
The first thing I did was implement the illusion of choice. Standards that we operated inside. Guardrails that enabled speed instead of friction. But I didn’t hand them down from on high and demand compliance.
We held daily standups where we spoke freely. What was working. What was not working. Where we could improve. This included the tools, the processes, how we tracked work, what “work” actually meant. Everything was on the table.
My job as the leader was to remove roadblocks and provide solid guardrails. Their job was to tell me honestly what was helping and what was hurting.
It wasn’t perfect. There were arguments. People disagreed. But over time, something shifted. The team found a common sense of purpose. We stopped fighting over tools and started building things that none of us could have built alone.
That’s psychological safety in practice. Not a policy. Not a workshop. A daily commitment to creating space where people can speak honestly without fear.
Build upward gradually.
Changing leadership’s mind is a long game. You won’t win it in one meeting. You might not win it in one year.
At the same organization, we had an ITSM system that leadership had committed to for partnership and financial reasons. As the architect, I saw the deficiencies clearly. I also saw that the decision had been made and “we should switch” wasn’t going to fly.
So I worked within the constraint. I outlined capabilities and deficiencies. I built workarounds for the inadequacies. And I collected data. Over time, I documented how the limitations were impacting users and customers. Real numbers. Real patterns. Real consequences.
At first, the direction was absolutely no change. But evidence accumulates. Patterns become undeniable. Eventually, the decision shifted. We moved to a new system in a staged approach that protected both financials and customer experience.
That took patience. It took consistent, honest feedback delivered without ultimatums. It took proving that I understood the constraints leadership was operating under while still advocating for what was right.
You won’t always win. But you’ll never win if you don’t play the long game.
Measure what matters, even if the organization doesn’t.
The critic correctly pointed out that measurement is organizationally expensive. Instrumentation takes effort. Feedback windows are long. People game metrics.
All true at the organizational level. Less true within your sphere.
You can define success criteria for your team’s decisions. You can track whether changes improved things or made them worse. You can build a local culture where honest measurement is valued, even if the broader organization doesn’t operate that way.
This does two things. First, it makes your team better. You learn from your decisions instead of just making them. Second, it builds credibility. When you can show leadership real data about real outcomes, you become someone worth listening to.
The preconditions don’t have to exist everywhere for you to start building them somewhere. Your team. Your domain. Your sphere of influence.
That’s where change begins. Not with a mandate from the top, but with a leader who decides to build something better within their reach.
When Leaving Is The Answer
Sometimes you’ve done everything right and the environment still won’t support good work.
You’ve built psychological safety within your team. You’ve led upward with patience and data. You’ve measured what matters and demonstrated value. And nothing changes at the level above you.
The feedback still gets punished. The decisions still get made by relationship instead of outcome. The organization still believes it has everything figured out.
This is when you have to make a different kind of decision.
Employees leave bad leadership, not organizations. At some point, after you’ve done everything to lead upward, tried your best to provide feedback, lived with the fear and frustration, you have to recognize when you’ve exhausted your options.
This isn’t failure. This is clarity about what you can and cannot change.
I’ve made this decision. The toxic environment I described earlier, I left quickly once I understood the reality. Not because I couldn’t do the work. Because the organization had no interest in letting me do it.
Staying would have meant compromising what I knew was right. Absorbing dysfunction until it became normal. Letting my own standards erode because the environment punished them.
Some people make that trade. I couldn’t.
Here’s what I want you to hear if you’re in this situation: leaving a broken environment is not giving up. It’s recognizing that you can’t serve where service isn’t valued. It’s protecting your ability to do good work somewhere else. It’s refusing to let someone else’s dysfunction become your own.
The hope isn’t that every situation is fixable. Some aren’t.
The hope is that you have a choice. You can recognize an unsalvageable situation clearly, without years of denial. You can leave before it damages you. You can find an environment that will let you build the things you’re capable of building.
That’s not a sad ending. That’s freedom.
The Bigger Question
If you’ve made it this far, you might be asking: if the framework requires all these preconditions, how does any organization build them? Who owns the work of creating psychological safety across teams, integrating decisions across domains, sustaining measurement over time?
These aren’t questions the Four Pillars can answer. The framework tells you how to evaluate decisions. It doesn’t tell you who makes them, where they live organizationally, or how the function sustains itself.
That’s a different question. And it’s the right question to ask next.
The servant leadership, the cross-domain integration, the long-horizon thinking that makes good decisions possible, these don’t happen by accident. Someone has to build them. Someone has to own the platform that everyone else builds on.
I call this the platform function. Not platform as in technology platform. Platform as in the foundation that holds everything else together.
What does that function look like? How do you build it in an organization that doesn’t have one? How do you scope it, staff it, sustain it?
That’s where “The Platform Layer” series picks up. If “Decide or Drown” is about what decisions to make, “The Platform Layer” is about building the organizational capability to make them well.
The framework isn’t incomplete. But it’s only one piece. The rest of the picture is about who does this work and where it lives.
The Light in the Darkness
Let me tell you what I actually believe.
The critique that prompted this post came from someone whose opinion I deeply value. A close friend who took the time to engage seriously with what I wrote and push back where it mattered. That kind of feedback is rare. It makes the work better. And it modeled exactly what this series has been arguing for: honest input delivered without fear, received without defensiveness.
They were right that the framework assumes things many organizations don’t have. What I hope this piece adds is that those things can be built. Not everywhere. Not by everyone. But by leaders who decide that their sphere of influence will operate differently.
Most organizations are imperfect. Most leadership is flawed. Most environments have dysfunction baked in somewhere. If you’re waiting for perfect conditions to do good work, you’ll wait forever.
But imperfect is not the same as hopeless.
You can create psychological safety on your team even if the broader culture doesn’t model it. You can be customer obsessed in your domain even if the organization chases quarterly numbers. You can measure honestly within your scope even if nobody above you wants to look at the data.
These pockets matter. They’re where good work actually happens. They’re where people learn what’s possible. They’re where the next generation of leaders sees something worth emulating.
And sometimes, those pockets grow. The team that operates well becomes the model other teams want to follow. The leader who builds trust becomes the leader others want to work for. The evidence that accumulates becomes impossible to ignore.
Change doesn’t start with a mandate from the top. It starts with someone who refuses to accept that dysfunction is inevitable.
That’s the hope. Not that every organization will transform. Not that every leader will become a servant. But that you have agency. You can build something better within your reach. You can influence upward with patience and evidence. And if the environment truly cannot support good work, you can leave with clarity instead of defeat.
The framework works when the preconditions exist. The preconditions exist when leaders build them.
Be that leader.
This is Part 4 of the “Decide or Drown” series. If you’re asking who builds these preconditions and where this work lives organizationally, that’s exactly what “The Platform Layer” series addresses.
Photo by Marielle Ursua on Unsplash
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