This Seat is Reserved: The Head of the Culture Snake

The Messy Monday Culture Problem Series | Part 2

Part 1 ended with a simple premise. Culture is not what you say. It is who gets heard, who gets promoted, and what happens when someone challenges the direction of the room.

So let’s start with who the heck is even in the room in the first place

The Boardroom Over Time

The Alliance for Board Diversity, in partnership with Deloitte, has tracked the composition of Fortune 500 boards since 2004. Shocker, there really hasn’t been much change in who sits in those fancy seats at the fancy table. Between 2004 and 2010, white men actually increased their share of Fortune 100 board seats, from 71.2% to 72.9%. So much for DEI taking everything over.

Progress came in increments over the following decade, followed by a surge in minority board appointments in the months after George Floyd’s murder in 2020. Think about that, it took a high profile, videotaped incident of violence against a black man to pressure some to, let’s be honest, appear, to become more inclusive. Between July 2020 and May 2021, 32% of newly appointed S&P 500 board members were Black, compared to 11% the prior year. And then the numbers stalled. Even in the boardroom the power dynamic is broken. As of 2024, women hold a record 29% of overall board seats but just 8% of board chair positions (The Conference Board / Russell Reynolds, 2024). Presence is not power. Those are different things, and it matters that we say so.

The fuller picture, across gender, race, and age together, looks like this:

A few things this table does not show still deserve naming.

The healthcare numbers look relatively strong at the workforce level. But in healthcare systems and services, while 70% of managers and 61% of senior managers are women, only 32% of C-suite roles are held by women (McKinsey / LeanIn, 2024). The pipeline fills because women have predominately filled healthcare roles like nurses, aides, therapists and staff support. They are seeking upward mobility, staying in the workforce longer, but the top closes.

The age data tells a story that gets almost no airtime in the diversity conversation: the average age of S&P 500 board members is 66, compared to 57 for executive team members, and the average S&P 500 leader is more than 14 years older than the general working population (Denominator, 2024).

The people making decisions about culture are, on average, a full generation removed from the people living inside it.

This taps into the recent podcast episode I did with a PA House candidate who is 26. He said that sometimes, what many call “inexperience”, is what is necessary to be able to see innovation and to promote change.

There is also a transparency problem layered underneath all of this. From 2024 to 2025, the share of companies disclosing racial and ethnic board data dropped 40% in the Russell 3000 and 32% in the S&P 500, following the court decision striking down Nasdaq’s board diversity disclosure rule (The Conference Board, 2025). When the data gets harder to see, the assumption should not be that things improved. It should be that the problem is getting harder to measure by design. Add onto that now, the removal and abandonment of DEI initiatives across organizations and the writing is on the wall.

But boards are only part of the picture. The senior leadership team, the people directly below the CEO making operational decisions every day, is where culture actually gets built or, other cases, dismantled. A Stanford Graduate School of Business study examining the C-suites of Fortune 100 companies found that women are underrepresented in the positions that feed into future CEO and board roles, such as CFO and P&L leadership. Ironic considering they have greater representation in positions less likely to lead to those appointments, such as general counsel or human resources (Larcker & Tayan, Stanford GSB, 2020). Women are in the room. They are consistently placed in the seats that do not lead to the next room, instead, they remain as the pillars that keep that room standing.

The composition of the room matters because industries develop norms based on who sits at the table, what gets rewarded, and what they define leadership to look like. Those norms become self-selecting. A homogeneous leadership team does not just reflect the past. It reproduces it.

When “Culture Change” Is Just a Leadership Swap

There is something organizations do not like to admit. Changing the name at the top is not the same as changing the culture, specifically when it comes as an attempt to improve the culture. When can easily verify that one person can immediately be detrimental and actually create a decline in culture, especially when they clean house as step one and insult those who stay as step two.

When it’s a performative effort to attempt to show dedication to improvement, we’ve all seen the predictable steps. The announcement goes out. A spokesperson hoorah’s the new leadership hire, saying “this is what we’ve needed”. The all-hands happens. The new values deck gets distributed. And then six months later, the people who thrived under the old regime are often still there, still operating by the old rules, and the new leader is either adapting to them or fighting a war on ten fronts with no institutional memory to draw on.

As much as we like to think you kill the bad culture by cutting the head of the snake, it’s more likely that the Board simply cut off the move visible rotten scale, but forgot the rest needed to go too.

Because, there are indeed times when the whole C-suite needs sent to new adventures, but often it only happens when a power hungry guru who thinks he (or she) knows best ends up as the chosen one.

The research on this is not ambiguous. Companies need to root out a bad leader’s followers among the rank and file and make important internal changes... otherwise a moral meltdown is likely to happen again. The leader is the visible problem. The culture is the operating system. It’s funny that “bad” leaders have figured out how to instantly gain the support team they need to protect themselves, but others have not.

Four cases show how this plays out. All four are documented in published academic and institutional research.

Wells Fargo

The Wells Fargo fraud scandal is a textbook case of culture failure dressed as performance management. After the 1998 merger with Norwest Bank, CEO Richard Kovacevich began referring to branches as “stores,” directing workers to see existing clients as targets rather than people. The culture shift happened in the vocabulary before it ever showed up in behavior. Call something a store long enough and people start acting like they work in one. Employees created over two million fake accounts in an effort to meet volume targets, with real fees but the accounts were never authorized by the people who held them. When the CEO resigned amidst the scandal, his replacement came from inside the same culture. The board changed the name at the top and called it accountability. Wells Fargo held my mortgage for years, last year they sold it with a month’s notice - no action needed, they assured me… but my insurance company wasn’t notified and I almost lost my coverage. Thank the heavens for a great insurance agent who helped me navigate it ASAP.

Steward Health Care

Steward Health Care was once the largest for-profit hospital operator in the United States, running 31 community hospitals across eight states. It filed for Chapter 11 bankruptcy in May 2024 in what became the largest healthcare provider restructuring in American history. The collapse was not sudden. Federal and state records showed nearly 680 deficiencies at Steward hospitals in the years leading to bankruptcy, climbing from 13 in 2020 to 108 in 2024, with the number of deficiencies per hospital roughly three and a half times the average for all US hospitals (Brookings Institution, 2025). Massachusetts Governor Maura Healey said publicly the situation stemmed from greed, mismanagement, and lack of transparency on the part of Steward leadership. Bankruptcy documents revealed that over $1 billion in dividends and payments flowed to insiders, executives, private equity investors, and affiliates, even as the company’s financial position deteriorated. Five hospitals closed. Approximately 2,400 workers lost their jobs. What the Brookings analysis described was not bad luck. It was a leadership culture with no functional mechanism for anyone to say that what was happening was wrong... and keep their job.

This isn’t specific to for-profit healthcare either. Right in the town I grew up in, a community hospital ended up in the same general predicament. A family of doctors fought over ownership of the hospital, which had one of the few mental health inpatient floors for teens in the area, floundered and eventually was forced to close after losing its license. The building was abandoned, vandalized, medical records just strewn across floors. The town couldn’t track down a responsible owner for the property and it took 20 years to tear the building down, happening only after it was set on fire so many times it became a major arson risk to the community.

Nokia

Nokia’s collapse has been analyzed in peer-reviewed academic literature, including in the journal Business History (Peltonen, 2018). The arc is instructive. When a new CEO took over in 2007, the top management team was revamped and the Chief Technology Officer position disappeared from the executive team. A technology company removed its most senior technical voice at the exact moment the industry was being redefined by software. You raised an eyebrow as your read that, I know you did. Employees knew Symbian was far behind Android, but engineers did not tell the truth to higher management, believing it was of no use. The culture had already taught them what happened when you raised inconvenient problems. Two CEO changes in five years deepened the instability rather than resolving it. Nokia lost around 90% of its market value in six years. A company that dominated the market, with almost everyone playing snake on their phones and swapping out their click on cases, dissolved into the history books.

Theranos

There are no shortages of podcasts and documentaries focused on Theranos, one of the rare female driven company case studies in this area. Harvard Business School also published a case study on Theranos as it was almost unbelievable and hard to wrap your head around (Fuller & Masko, 2019). The board failure there was not primarily one of misconduct. It was one of composition. The board was assembled for prestige and political access, not for oversight, and lacked the expertise to challenge what it was being told. Teams were not allowed to communicate transparently, let alone raise concerns that might contradict what leadership hoped to hear. Would-be whistleblowers were threatened with lawsuits. 175,000 Arizona residents received faulty blood tests. The structure of the board made the fraud possible. The culture made it invisible until it was not. This isn’t even a fraction of what will make your head spin about this case. The CEO is in jail, the Board meanwhile, is probably still wondering what exactly the product was that they were overseeing in the first place.

Uber

Uber is the most instructive case precisely because the culture change was indeed, attempted seriously. New CEO Dara Khosrowshahi came in as an acknowledged outsider, publicly committed to changing what the prior leadership had built. But, as we’ve noted, culture is embedded throughout an organization, so replacing a person or two is not enough... you have to show you are serious by bringing in experts, assessing the situation honestly, and putting concrete processes in place (Larcker & Tayan, Stanford GSB, 2018). What Uber discovered was that the people who had thrived under an aggressive, win-at-any-cost environment did not simply change because the leader did. Some left. Many stayed and continued operating by the norms they knew. Change at the top is necessary. It is not sufficient. One person cannot single handedly build immediate trust, institute new recognition and rewards and cannot coddle everyone who was happy the way it was.

Fear Is Not a Side Effect. It Is the Mechanism.

In many of these cases, people knew there were issues. Some went the whistle blowing route. Others may have taken part in malicious compliance. Others, may have just gone numb. To combat that, there have been efforts overtime to bring a very “all are welcome” feeling to the work place. Well intended but not well understood.

There is a term that has made its way into nearly every leadership conversation of the last decade: psychological safety. Like most things that become buzzwords, it got there because it describes something real. And like most buzzwords, the repetition has flattened what it actually means. Most of us probably don’t even truly understand what it means.

The concept comes from Harvard Business School professor Amy Edmondson, whose 1999 paper in Administrative Science Quarterly defined team psychological safety as a shared belief that the team is safe for interpersonal risk taking, and found it directly associated with learning behavior and team performance. That paper has been cited nearly 100,000 times. Google’s internal Project Aristotle study identified it as the single most important factor in high-performing teams.

What gets lost in the buzzword version is that this runs in both directions. The coverage tends to focus on the employee who cannot speak up. But the mechanism operates at every level of the organization. Research on 1,150 leaders in 160 management teams found that psychological safety functions throughout the entire organizational hierarchy, and that managers who perceive the climate as safe are more likely to collaborate, share information, and take ownership of decisions (Mogård, Rørstad & Bang, International Journal of Environmental Research and Public Health, 2023).

Read that again if you manage people.

You are not just a conduit for decisions made above you. You are also someone who needs to be able to push back on those decisions, flag when the direction does not make sense from where you sit, and say out loud when the thing being asked of you is going to land badly on the people you manage. If the culture above you makes that feel like a career risk, the silence does not stay with you. It travels down. And the people below you learn, fairly quickly, what kind of room they are in.

This is also worth sitting with on the other side of the table. The version of psychological safety that has filtered into most organizations has quite honestly made actual management harder. A stern tone, negative feedback or lack of thorough communication gets internalized into fear for many, no matter the context.

Giving someone direct feedback on work that is not meeting the standard is not a safety violation. Documenting a performance issue before it becomes a formal grievance is not retaliation. Having the conversation about behavior or output before it escalates to HR is not creating a hostile environment. Encouraging brevity for time management is not oppression.

These are the basic functions of management. But in workplaces where the concept has been stretched past its research definition, managers have learned that initiating any of those conversations carries risk. Not because the conversations are wrong. Because the response to them has become unpredictable.

So they stop. They write the performance review that says “meets expectations” or “exceeds expectations” for someone who does not. They let the grievance build until it lands on someone else’s desk. They default to the path that generates the least friction in the short term and the most damage in the long term. The person on their team who actually needed the feedback never got it. That is its own kind of failure, and it belongs in this conversation.

I’m guilty of all of this. And when I realized it and implemented clear and measurable expectations, I had team members panic. My time became filled with mediation, coaching and increased one on ones with staff who, made six figures but now demanded hand holding. HR shook their head, said they knew it was a waste of time because the appeals wouldn’t change anything but someone invoked the magic works… “hostile”, “discrimination”, “violation”… The findings never supported the allegations, but it’s one of the reasons I left people management. No matter the joy in the wins I saw in 80% of my team, the other 20% stole it away.

Edmondson’s original research was explicit on this point. Psychological safety is not about comfort. It is about candor. The condition that makes honest conversation possible in both directions... the employee who can raise a concern without fear, and the manager who can give direct feedback without fear. When only one direction is protected, you do not have safety. You have managed silence.

Adults can have feelings and still be held to a standard. Those two things have never been in conflict. We have just built systems that act like they are.

The research uses other language for the same underlying construct, language worth knowing because it has not been worn smooth yet:

• Interpersonal risk climate: the degree to which people believe speaking up will be punished or rewarded

• Organizational voice: whether employees have real channels to surface concerns, not just nominal ones

• Learning culture versus performance culture: organizations where mistakes get analyzed versus organizations where mistakes get hidden

• Accountability without retaliation: the ability to name a problem and have it investigated rather than have it used against you

All of these describe the same gap. The distance between what an organization says it values and whether people actually believe it is safe to act on those values.

Research published in the Academy of Management Journal found that teams with low psychological safety experience 38% more rework and missed deadlines than those with strong safety climates, even when skill levels were equal (Schweitzer et al., 2023). The cost is not abstract. It shows up in the work, the timeline, and eventually the outcome.

Fear is not a side effect of a bad culture. It is the mechanism by which a bad culture reproduces itself.

People learn what is safe to say. They calibrate. And eventually the only voices reaching the top are the ones that were never going to say anything inconvenient.

The Yes-Men Problem

There is a pattern that deserves its own name. The leader who does not simply tolerate agreement, but actively constructs it. Who surrounds themselves on arrival with people who reflect their own perspective back without friction. Who promotes the loyal and sidelines the skeptical. Who calls this alignment.

It has a name in the research. Homophily, the human tendency to trust, associate with, and ultimately hire people who resemble yourself. Deloitte research on inclusive leadership identifies homophily as a primary bias that leaders must actively counteract, noting that without intentional intervention, a leader’s natural state tends toward self-cloning (Deloitte Insights, 2016). Self-cloning is not a personality flaw. It is a gravitational pull. The question is whether an organization has built the structures to resist it.

Think about the CFO question. A CEO who hires a CFO who thinks exactly the same way gains operational alignment. They may also gain a blindspot with a budget. Who brings the counterargument? Who challenges the growth projection? Who asks what happens if the assumption is wrong? BCG research found that replacing as few as 2% of the total management team with people from different industries improved innovation revenue by a full percentage point (Lorenzo et al., BCG, 2018). Diversity of thought is not a values statement. It is a performance variable.

Irving Janis named this in 1972. Groupthink. The structural conditions that make it likely: insulation of the group, lack of impartial leadership, homogeneity of members. His research showed that groups with leaders who announce their positions before discussion begins are more likely to reach biased conclusions. Not because the people in the room are unintelligent. Because the room itself has already communicated what the right answer is.

We have dressed this up considerably since 1972. Open door policies. Town halls. Anonymous feedback surveys. Suggestion boxes that became digital platforms that became engagement dashboards. The infrastructure of listening has never been more elaborate. And yet the person who walks through the open door with a problem that implicates someone powerful still gets labeled. Not a whistleblower, not even a dissenter. Just... difficult. A troublemaker. Not a team player. Someone who does not understand how things work around here. The title I received in my last few months in the federal government by those in the Secretary’s inner circle.

The subject matter expert who has been doing this job for fifteen years raises a concern about the new direction. The room nods politely. The decision proceeds unchanged. And if that person keeps raising it, at some point the label sticks. High reliability organizations, the ones that study this most carefully, including aviation, and nuclear systems, have documented what happens when the SME gets dismissed in favor of the person with the title. It is not a theory. It is an accident report. Yet - in healthcare, it happens constantly.

The clique is not always visible. It does not announce itself. It shows up in who gets included on the email chain and who gets the summary after the fact. Who gets invited to the informal conversation before the formal meeting where everything is technically still open. Whose feedback lands as insight and whose lands as complaint. The cool kids table in a workplace does not have a sign.

It has a seating chart that everyone can read and nobody is supposed to acknowledge.

If you manage people, you have felt this from at least one direction. The moment you registered that the decision had already been made before the conversation started. The question you did not ask because you had read the room well enough to know it would not land. The person on your team who stopped bringing problems to you because they had learned, somewhere along the way, that it was not worth it. Or the person who did bring it, and watched it go nowhere, and then got quietly moved off the project.

That is not a character failure on anyone’s part. That is a culture doing what cultures do when the open door is real but the welcome is not.

The Federal Government as the Most Transparent Example

Every organization has a version of this dynamic. The federal government makes it legible in a way that private organizations rarely do, because the data is public, the structure is documented, and the consequences are measurable.

A political appointee is exactly what it sounds like. When an administration changes, the incoming president has the authority to appoint individuals to leadership positions across the federal government, roughly 4,000 of them, ranging from cabinet secretaries to agency heads to senior advisors. Some of those positions require Senate confirmation. Many do not. What they share is that they are filled based on political alignment, not competitive merit process.

You do not apply for most of these roles the way you apply for a job. You are known to the right people. You supported the right campaign. You believe what the administration believes, or at least you say you do convincingly enough.

Underneath those appointees sits the career workforce. Federal employees who came in through a competitive hiring process, who are legally required to serve regardless of which party holds the White House, and who, in theory, provide the institutional memory and subject matter expertise that keeps government functioning across administrations. They are not supposed to be partisan. They are not supposed to change with the political winds. That is the design. A professional civil service that outlasts any single election.

The design has always been imperfect. But the degree to which it holds matters enormously for how well the government actually works.

The civil service as a formal structure dates to the Pendleton Act of 1883, passed specifically in response to the spoils system, where government jobs went to political loyalists regardless of qualification. The reform was direct: hire on merit, protect from politically motivated firing, create a workforce that serves the public rather than the party in power. It was not a perfect system. It was a deliberate correction to something that had been visibly failing. So why the huge exception to the top 4000 people with power in the system?

What the research shows about what happens when that correction unravels, is quite blunt.

Studies of the federal bureaucracy find that agencies with more political appointees have slower responses to information requests and more expensive government contracts, and that rank and file employees in those agencies report fewer behaviors associated with good management and lower regard for agency leaders (University of Chicago Center for Effective Government, 2024).

The concern is not partisan. It applies regardless of which party is doing the appointing. It is structural. When the people at the top are selected for what they believe rather than what they know, the organization underneath them calibrates accordingly.

Career staff learn quickly what the new leadership wants to hear. The ones who provide it move up. The ones who do not get reassigned, sidelined, or pushed out through mechanisms that are technically legal and operationally familiar to anyone who has watched a loyalty-first culture operate in any sector. The institutional knowledge walks out with them. The early warning system does not fail dramatically. It just quietly stops working.

This is the blue and red boardroom problem, and it repeats on a four or eight year cycle regardless of the blend of purple doing the work. The staff underneath are expected to be nonpartisan professionals. The leaders above them arrive as ideological representatives. And the gap between those two things is where expertise goes to get dismissed as resistance.

The ACFE’s 2024 Report to the Nations finds, again, that whistleblowers, the people closest to the work, detect 43% of all occupational fraud. Not the auditors. Not the executives. The people who, in a loyalty-first culture, are exactly the ones who get moved out first. Not because they are wrong. Because they are inconvenient.

That is not a coincidence. That is the culture working exactly as designed.

Next week: The American workplace did not happen by accident. Part 3 looks at what we got right, what we exported as a problem, and what the rest of the world's approach to work tells us about our own.

Sources:

• Alliance for Board Diversity / Deloitte Missing Pieces Report (2004–2022)

• The Conference Board / ESGAUGE / Russell Reynolds / KPMG Board Practices and Composition Report (2024–2025)

• Spencer Stuart 2025 U.S. Board Index

• McKinsey/LeanIn Women in the Workplace 2024

• Denominator, S&P 500 Age Leadership Distribution (2024)

• Larcker, D. & Tayan, B., “Diversity in the C-Suite,” Stanford Graduate School of Business (2020)

• Larcker, D. & Tayan, B., “Learning from Uber’s Mistakes,” Stanford Graduate School of Business (2018)

• Brookings Institution, Goldstein & Agarwal, “Lessons from the Collapse of Steward Health Care” (2025)

• Peltonen, T., “The Collapse of Nokia’s Mobile Phone Business,” Business History (2018)

• Fuller, J. & Masko, J., “Theranos: The Unicorn That Wasn’t,” Harvard Business School Case 319-068 (2019)

• Edmondson, A.C., “Psychological Safety and Learning Behavior in Work Teams,” Administrative Science Quarterly (1999)

• Mogård, E., Rørstad, O.B. & Bang, H., “Psychological Safety and Management Team Effectiveness,” International Journal of Environmental Research and Public Health (2023)

• Schweitzer, V. et al., “The Limits of Psychological Safety,” Organizational Behavior and Human Decision Processes (2023)

• Lorenzo, R. et al., “How Diverse Leadership Teams Boost Innovation,” BCG (2018)

• Deloitte Insights, “Six Signature Traits of Inclusive Leadership” (2016)

• Janis, I.L., Victims of Groupthink (1972)

• University of Chicago Center for Effective Government, Political Appointees to the Federal Bureaucracy (2024)

• ACFE, Occupational Fraud 2024: A Report to the Nations