The Cultural Compartmentalization Paradox

Ever been part of a "Cultural Initiative"?

It goes something like this:

Why didn't we see what we expected?

IMPORTANT: In this post, I'm making the assumption that our intent to change the culture is genuine. There's a whole other category of companies who are NOT executing their cultural initiatives in good faith with real intent - they feel like they're being bullied into conceding to their workforce, and their efforts are simply token attempts. Those are doomed to fail for much more obvious reasons!

The problem is that we're treating our culture like a project, with scopes, deadlines, KPIs, OKRs, and other TLAs (Three-Letter Acronyms 😏).

Why Project Thinking is Ineffective in This Context

"That's a bold statement, Blink. Project Thinking is How We Solve Problems." (My friend Robert Roskam introduced me to a concept called the Einstellung Effect... I'll just leave that there for you to dot-connect with 😬)

Let's look at some reasons why Project Thinking isn't working for us here.

Culture is lived, not delivered.

How do we use projects to approach problem-solving? We define the work in a sprint, focus our efforts on doing exactly what we define, and measure quickly in order to adjust our next sprint.

On the other hand, Culture is deeply rooted in the emotional realm. Culture doesn't behave like a project domain; it isn't linear, predictable, or easily measured in short cycles. Its tentacles reach into feelings and beliefs and motivations and those "squishy" places where metrics are incredibly hard to define.

It's a fallacy to think we can define something like Culture in a finite, linear initiative!

Project Management Tools Aren’t Built for Culture Work

Building on that last point - none of your Project Management Tools can define this kind of "infinite" project well. You'll always have to make some sort of logical concession that breaks the analogy.

Your traditional "Project Budget" and roadmapping processes aren't going to handle this well either. Let's face the facts, our roadmaps rarely get software delivery exactly right (and if you disagree, show me you've never slipped a deadline... I'll wait! 😏) - so imagine how much harder it would be to "deliver" Psychological Safety in Q3! Every cultural effort is going to either have a murky end date or become a maintenance task. Your goal is to get it to "become the Culture"... but how long it will take to learn that Way is always going to surprise you.

Metrics and the Fallacy of ROI

We live in a world where everything has to be managed, measured, and instant. There's a continuous obsession with "Return on Investment"... and a complete lack of patience to wait for that return.

But Culture change doesn't work like that. People's minds don't change instantly. Their hearts won't warm overnight. Trust takes time to build. Almost by definition, we have to wait for results... and measuring feelings isn't exactly a science, so even when those results roll in, the metrics-obsessed folks are still going to struggle.

Another thing to remember here is that Culture is lagging, not leading. You'll have to account for some time to pass between changes that you make and the results you expect. How much? Well... some. There's no set pattern to it!

The Compartmentalization Paradox

Let's give a name to what's happening here: The Compartmentalization Paradox.

The paradox is this: companies treat culture as a discrete, bounded project — assignable, trackable, and temporary — while simultaneously expecting it to influence everything, pervasively and permanently.

Culture is not something you install, it's something you become. Yet organizations consistently try to slot "culture work" into the same lanes as product launches or cost reduction initiatives. This creates an unresolvable tension: they want widespread behavioral change, but they constrain it to a budget, timeline, and/or team. Here's how and why things go wrong:

Culture is Not a Department

If the company detects a cultural factor in play, such as attrition, lack of engagement, or morale problems, they'll often react to that by assigning it to HR... or DEI... or they might create a special task force.

This is the first act of compartmentalization: culture becomes someone’s job, rather than everyone’s responsibility.

This is how culture becomes performative and cheap instead of impactful and rich. Employees know when culture is a checklist rather than a lived experience, and management knows — deep down — that they’ve just moved the problem instead of addressing it.

Cultural Initiatives vs Cultural Norms

Here’s how the paradox creates failure: conflating surface-level initiatives with the deep structure of workplace norms.

An Initiative is a thing you do: a town hall, employee appreciation week, a social event, an offsite.

A Norm is thing you are: inclusivity in decisionmaking, how you treat a mistake, how you distribute power and influence.

Companies love initiatives because they feel more like Projects: they're time-bound, budgetable, and (often) measurable. But if the day-to-day experience of work doesn’t change — if people still feel unseen, unsafe, or undervalued — your culture hasn’t shifted. You’ve decorated the surface while the foundation stays cracked.

Lipstick on the Org Chart

It’s tempting to “show progress” by pointing to visible changes: a new Slack channel, some branded mugs, maybe a clever mascot for the culture campaign.

But none of that matters if the lived reality remains misaligned. If performance reviews punish collaboration, if promotions reward burnout, if meetings are silent because no one feels safe speaking up — then the culture project has failed, no matter how nice the swag looks.

Real culture work is invisible at first. It shows up in how people feel when their manager messages them. It shows up in who speaks in meetings — and who doesn’t. It shows up in whether people believe what leadership says.

As a leader, are you willing to do the right thing even if it's invisible? Even if you can't directly receive credit for it?

So What Does Work?

On the surface it seems like the Paradox has no good news for us. It's very good at highlighting things that aren't working... but what should we do instead?

Long-Term Commitment, Not Quick Fixes

If we recognize that culture is not a finite project with a strict budget and timeline, it leads us to understand that our culture is a long-term investment. It should be established early and then continually cultivated... frequent tweaks and adjustments are healthy and useful (but probably not complete overhauls... don't fall in the "continuous reorganization" trap!).

The companies that make meaningful cultural shifts are the ones willing to:

• Stick with the effort for years, not quarters.

• Accept ambiguity and lack of short-term proof.

• Change course based on internal feedback, not just external benchmarks.

It’s not sexy. It doesn’t demo well. But it works — slowly, then suddenly, like compound interest.

Leadership Behavior is the Real Lever

Nothing undermines a cultural initiative faster than misaligned leadership behavior!

You can’t promote “psychological safety” in a presentation and then shut down honest feedback in a meeting.

You can’t reward aggressive individualism and expect teamwork.

You can’t talk about inclusivity and never give underrepresented voices actual decision-making power.

The most successful cultural transformations start with leaders modeling the behaviors they want to see — even when it’s uncomfortable, even when it slows things down.

Culture follows credibility, not slides.

Embedding Culture in How Work Gets Done

It will be tempting to do something like "rewrite our Values together" and then look for ways to impose the new Values on initiatives that promote them. But the danger here is in treating your culture like it's something "extra" instead of building them directly into our day-to-day work!

Look: I get it, initiatives are satisfying because they have that finite "project" feel to them. But you know what's actually tons more effective? Making the values the actual DNA of your company!

How? Fewer initiatives. More Norms.

• Hiring: Don’t just hire for skill — hire for how someone affects the team dynamic.

• Onboarding: Introduce cultural norms alongside job duties.

• Decision-making: Bake in practices that reflect your values — transparency, inclusion, accountability.

• Performance reviews: Evaluate how work is done, not just what gets done.

It's very simple to say but will require incredible discipline to execute:

If you want collaboration, reward it.

If you want innovation, protect time for it.

If you want trust, build systems that reinforce it.

Culture isn’t an initiative — it’s the operating system.

Wrapping up

The Cultural Compartmentalization Paradox persists because it offers the illusion of control. Treating culture like a project makes it feel manageable: scoped, budgeted, contained. But real culture doesn’t live in plans or slide decks. It lives in how people treat each other when no one’s watching.

If you want to change your culture, stop asking, “What initiative should we launch?”

Instead, the right questions are “What do we reward? What do we tolerate? What do we model?”