There’s a need for change.
The executive team conducts a gap analysis.
What isn’t working in the current culture?
What kind of culture do we want instead?
Which values need clarification or refreshing?
Then the leaders take the stage to announce the change – this is how we’ll do things in the future.
Some go the extra mile, printing out shiny cards with new values and continue repeating the new mantras in all their meetings.
On paper, it makes sense. Diagnose the problem. Define the aspiration. Align around new principles. And yet, despite well-laid-out plans, there’s little movement. Months later, the old cultural habits quietly return.
The reason is rarely a lack of good intentions. It’s structural.
Culture behaves less like a set of declared values and more like an operating system. It sits beneath strategy, processes, incentives, and daily interactions. It shapes how conversations happen, how decisions are made, how power moves, and what behaviors actually get rewarded.
When leaders try to change culture by rewriting values or refining language, they are mostly changing the interface. The deeper system – the assumptions embedded in processes, the symbols that signal what truly matters, the trade-offs that get rewarded under pressure – remains intact. And like any system, it tends to protect its own logic.
If a problematic work culture maintains its grip, it’s not because people resist change. It’s because the operating system still runs the same code. To weaken that grip, leaders have to look below the surface. They have to examine the processes that drive behavior, the symbols that define status, and the reinforcement mechanisms that quietly shape performance.
The following questions are not meant to inspire alignment. They are meant to help leadership teams look inside the system itself and identify where it continues to reproduce the very patterns they say they want to change.
That’s where the real work begins.
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Surfacing the Tolerance Gaps
Most organizations can articulate their values clearly: collaboration, accountability, transparency, well-being or similar principles. And yet, under pressure, leaders often tolerate behaviors that contradict those values, especially when performance numbers look strong. A high performer who undermines peers remains protected. A leader who centralizes decisions in the name of speed continues to advance.
No one frames this as hypocrisy. It feels pragmatic. Temporary. Necessary.
Over time, though, the tolerated behavior becomes the norm, trumping over the declared value.
The question
What’s one behavior we tolerate that shapes our culture more than any value we promote?
Recently, I was with an executive team wrestling with this simple but uncomfortable question. They spoke about becoming a company where respect truly matters. Yet as the conversation unfolded, a few sarcastic jabs slipped in, masked as humor. No one addressed them. The room moved on. I paused and pointed it out. In that moment, it was clear: what they were tolerating was shaping their culture far more than what they were saying.
When leaders answer this honestly, the conversation shifts from aspiration to reflection. The focus moves away from rewriting principles and towards examining what actually happens under pressure.
Once the tolerated behavior is named, it becomes harder to justify it as an exception. It becomes visible as a structural choice. That’s often the first moment the system becomes visible.
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Understanding How Influence Actually Moves
Formal authority is clear. Org charts define reporting lines and decision rights.
Influence, however, often flows in different ways.
In some systems, proximity to power matters more than competence or formal titles. In others, avoiding friction carries more weight than thoughtful challenge. Employees learn quickly which behaviors grant access and which ones create distance.
These patterns are rarely discussed openly, yet they shape behavior every day.
The question
What does someone have to do to gain influence here, beyond what’s written on paper?
When leaders explore this question seriously, they often discover that the real currency of influence differs from the stated leadership model.
Mapping informal influence exposes where the system rewards compliance over courage, or speed over depth. That visibility gives leaders the opportunity to realign influence with the culture they claim to want, instead of allowing invisible dynamics to keep driving behavior.
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Promotion Patterns and the Definition of Success
Promotion decisions reinforce the behaviors that are considered successful. Over time, they define what “good leadership” actually means, regardless of stated values.
The question
What do our most successful leaders have in common? What does that say about us?
Looking closely at promotion patterns reframes advancement as a cultural signal, not just a talent decision.
For example, I was working with a leadership team that spoke passionately about building a culture of experimentation and bold ideas. But when we looked at who they were promoting, a different pattern emerged. In a conversation about a high-potential candidate who wasn’t “quite ready” but had the courage to challenge the status quo, the room hesitated. The concern wasn’t about potential, it was about certainty.
Leaders often assume they are rewarding merit. But merit is always defined by the system in place. When the criteria are made explicit and examined, it becomes possible to ask a harder question: are we selecting for the kind of leadership we will need in the future, or reinforcing what worked in the past? Promotion then stops being a neutral outcome. It becomes one of the most powerful levers for shifting the operating system.
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When Values Feel Fragile
Values tend to feel stable in normal conditions. In workshops and town halls, they appear clear and shared. But pressure reveals their real strength.
When deadlines tighten or financial struggles dominate the agenda, leaders face trade-offs. Transparency competes with reputation. Inclusion competes with speed. Well-being competes with urgency. In those moments, decisions are rarely framed as cultural choices — they are framed as business necessities.
Over time, people learn which values hold when tested and which ones bend.
The question
When do our stated values feel most performative, or disconnected from daily reality?
Identifying the precise moments where values weaken shifts the focus. The issue stops being whether people “believe” the values and starts being whether the surrounding decision conditions make them viable.
The conversation moves from moral alignment to structural alignment. From urging consistency to redesigning how trade-offs are handled. Instead of asking why people fall short, the system itself becomes the object of examination.
That’s where the operating system begins to loosen.
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Inertia as Strategy
Practices that once created success often become part of organizational identity. Alignment becomes thoroughness. Discipline becomes caution. Loyalty becomes resistance to change.
Because those traits contributed to past performance, leaders rarely question them. They feel earned. They feel foundational.
Over time, what began as a strength becomes self-protective. The organization defends familiar patterns even when the environment shifts.
The question
What parts of our culture would our competitors love for us to keep?
This question reframes tradition as a variable rather than a given. What once felt like identity becomes open to strategic scrutiny.
Separating what is essential from what is habitual allows the organization to preserve its strengths without protecting its constraints. The past is no longer defended automatically; it is evaluated deliberately.
That shift reduces the grip of inertia without erasing what originally created value.
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The Discipline of Unlearning
Transformation efforts usually focus on addition. New competencies. New structures. New leadership behaviors.
Rarely do leaders examine what must be released.
Yet problematic work cultures often persist not because something is missing, but because something outdated remains protected. A decision pattern. A leadership reflex. An unspoken assumption about control or speed.
When those patterns stay intact, new initiatives simply layer on top of old logic.
The question
What will we need to unlearn?
Unlearning shifts the focus from adding more to carrying less. It asks leaders to confront the habits that once made them successful but now hold them back. It challenges identity and credibility because it requires subtraction, not addition. And subtraction is what disrupts inertia.
A pattern I see often comes up around delegation and empowerment. Leaders will say they need to lead more strategically, to focus on a few critical things, and create more space for innovation. But when we look closer, letting go is hard. In one conversation, a leader admitted he struggled to step back because he felt he needed to have the answers and ensure things were done “the right way.” What sat underneath wasn’t capability, it was control. Staying close to the details gave him certainty, comfort, and a sense of value. Letting go meant giving that up and stepping into work that felt less familiar, more ambiguous, and harder to master.
When leaders name what needs to be let go, not just what needs to be built, they move beyond surface change and start questioning their assumptions. The harder step is asking why they’ve held on for so long, and what those old ways have been giving them.
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Culture and Performance Are Interdependent
Many leadership teams treat culture and performance as parallel tracks. One belongs to HR conversations. The other lives in dashboards and quarterly reviews. In reality, they feed each other constantly.
Short-term results often legitimize behaviors that would otherwise be questioned. A leader who delivers under pressure may get latitude for dismissiveness. A team that hits targets may receive less scrutiny about how collaboration actually unfolds. Over time, performance begins to grant moral cover.
What began as a temporary exception turns into a recurring pattern.
Behavior produces results. Results justify behavior. The loop tightens.
The question
What behaviors are our current results encouraging, and where will those behaviors take us if they continue?
As soon as performance is examined through a behavioral lens, the conversation shifts from “Did we hit the number?” to “What did we normalize in order to hit it?”
That reframing introduces time into the equation. It forces leaders to consider second-order effects: whether today’s success quietly erodes tomorrow’s adaptability.
When that loop becomes visible, leaders can intervene earlier — not by rejecting performance, but by redefining which performance is worth reinforcing.
Culture stops being the soft side of the business. It becomes the mechanism through which results are produced — and reproduced.
Treat the System, Not the Surface
Wrong culture doesn’t loosen its grip because values were rewritten or language became sharper. It loosens when leaders are willing to confront what actually drives behavior. Especially the parts that are hidden or feel uncomfortable to name.
That means confronting the tolerated contradiction, the invisible pathways to influence, the promotion patterns no one questions, and the habits that once worked but now constrain.
Surface-level fixes soothe symptoms. They rarely alter the operating system.
Real cultural change begins when leadership teams step into the hard questions without defensiveness, when they stop asking how to appear aligned and start asking what must shift beneath the surface.
That requires courage. It requires looking at reinforcement mechanisms, not just intentions. It requires changing processes, symbols, and behaviors, not just narratives.
Culture will not correct itself through aspiration.
It changes when leaders decide to treat the cause, not the symptom.
