Leadership Anxiety in the Modern Workplace
There is a particular kind of executive anxiety making the rounds in corporate America right now. It is not the anxiety of missing quarterly targets or navigating geopolitical supply chain disruptions. It is quieter and considerably more personal: the fear of saying the wrong thing at the team offsite, of a joke landing badly, of being the subject of a thread that takes on a life of its own before Monday morning.
Callum Borchers captured this tension sharply in his Wall Street Journal piece, “How to Be a ‘Cool’ Boss Without Getting Fired,” published in August 2026. The article chronicles managers caught between the desire to be liked and the very real professional consequences of misreading the room. But the piece raises questions that go well beyond workplace etiquette. It points to something more structural: a fundamental redefinition of what effective, respected leadership actually looks like in the modern organization.
Why the “Cool Boss” Playbook No Longer Works
The core argument Borchers advances is straightforward. The traditional markers of a “cool” boss—late nights with the team, edgy humor, spontaneous antics at company retreats—no longer serve managers well in a professional landscape shaped by social media scrutiny, generational value shifts, and a record number of workplace complaints.
The examples he cites are not abstractions: a startup CEO ridiculed online for tattooing employees as a hiring gimmick; a former Netflix vice president terminated after oversharing personal health struggles at a company event; a Boston transit authority facing a nearly $500,000 settlement because a well-liked general manager crossed a physical boundary during what was supposed to be a lighthearted dinner.
These are not cautionary tales about bad people. They are cautionary tales about good intentions colliding with a fundamentally changed workplace culture.
Borchers is right to frame this as a managerial challenge rather than a morality question. Most of the leaders he profiles are not villains. They are people who came up in professional environments where the rules of engagement were different and who have not yet recalibrated their instincts for a new context. The millennial manager Shannon Leiro puts it plainly: “You just have to have an automatic filter.” That sentence, as mundane as it sounds, actually captures a sophisticated professional truth. Good leadership has always required contextual intelligence—the ability to read an audience and adjust accordingly. What has changed is that the audience has changed, and the consequences of getting it wrong have become far more visible and far more costly.
The Real Cost of Misreading the Room
The legal and reputational stakes Borchers identifies deserve closer examination than the article affords them. Equal Employment Opportunity Commission complaint volumes are not just a barometer of workplace misconduct; they are also a signal of shifting employee expectations and a growing willingness to assert rights. According to EEOC data, harassment charges—a significant category within overall complaints—have been showing renewed momentum after years of post-#MeToo plateau. Organizations that treat this as background noise do so at their peril.
The Boston MBTA settlement is particularly instructive. The general manager in question was, by accounts, popular. That popularity did not insulate him from accountability when his behavior crossed into physical contact without consent. This illustrates a critical blind spot among otherwise well-regarded leaders: the assumption that goodwill accumulated over time creates a buffer against missteps.
Research published in the Journal of Applied Psychology suggests the opposite dynamic can occur—what scholars call the “moral licensing” effect, where a track record of positive behavior can actually lower a person’s guard and lead to lapses in judgment (Jordan, Mullen, and Murnighan, 2011). Managers who believe their reputations protect them may be the most at risk.
The Netflix case adds another layer. The former vice president who disclosed his ketamine use and performed a headstand while drinking at a company retreat was not, by most conventional measures, doing anything malicious. He was, in all likelihood, trying to connect with colleagues and signal authenticity. But authenticity has boundaries in organizational settings, and those boundaries are not always where leaders assume them to be.
Oversharing personal health information—even framed as vulnerability—can blur professional hierarchies in ways that create discomfort for subordinates who feel unsure how to respond.
Psychological Safety Is Not the Same as Permissiveness
One of the more important distinctions that Borchers’ article gestures toward but does not fully develop is the difference between psychological safety and permissiveness. These two concepts are frequently conflated, and the conflation creates real problems for managers.
Psychological safety, as defined by Harvard Business School professor Amy Edmondson in her foundational research, refers to a team climate in which members feel safe to take interpersonal risks—to speak up, admit mistakes, and raise concerns without fear of punishment or humiliation. It is a condition that enables learning and performance. Critically, it is not about lowering standards or removing accountability. It is not about the boss being fun to drink with.
Edmondson’s research across healthcare teams, manufacturing floors, and corporate environments consistently shows that the leaders who build psychologically safe teams are those who model humility, invite input, and respond constructively to bad news—not those who throw the best office parties (Edmondson, 1999).
This distinction matters because many managers have internalized a folk theory of workplace culture that equates looseness with safety. If the boss lets his hair down, the theory goes, employees will feel more comfortable. Sometimes this is true. More often, the asymmetry of organizational power means that what feels liberating to the person at the top of the hierarchy feels pressuring or awkward to those below.
An employee who does not want to stay out until midnight or discuss their mental health in a group setting should not have to navigate that discomfort as the price of seeming like a team player.
The Generational Recalibration
Borchers correctly identifies generational change as a driving force behind the new workplace norms. The entry of Generation Z into the workforce in meaningful numbers has introduced a cohort shaped by different experiences and different expectations. Research from Deloitte’s annual Global Millennial and Gen Z Survey consistently finds that younger workers place higher value on mental health, work-life boundaries, and inclusion than their predecessors did at the same career stage.
They are also more likely to have grown up with social media as a constant presence, which means they have an internalized sense of how quickly a moment can be broadcast, interpreted, and judged.
This does not mean Gen Z workers are humorless or fragile—a charge that gets leveled with tedious regularity. It means they have a different calculus for what constitutes appropriate professional behavior, and they are less willing to absorb discomfort in silence. Managers who dismiss this as oversensitivity are making a strategic error.
The same workers who are most likely to push back on clumsy attempts at bonding are also the ones organizations are competing hardest to attract and retain in a tight labor market.
Shannon Leiro’s approach—replacing late nights with structured acknowledgment rituals in team meetings—is a reasonable adaptation, even if she calls it “cheesy.” What she has understood is that the goal of creating team cohesion does not require a particular delivery mechanism. The goal is connection, recognition, and a sense of belonging. There are ways to achieve that goal which carry no risk of crossing lines, and smart managers are building their cultures around those methods.
When Authenticity Becomes a Liability
One of the subtler tensions in Borchers’ piece is the question of authenticity. Many leadership development frameworks of the past two decades have urged executives to bring their “whole selves” to work, to lead with vulnerability, to shed the armor of professional distance. Books like Brené Brown’s Dare to Lead have made the business case for emotional openness persuasively and with substantial research backing. The message has resonated widely.
But authenticity in leadership is not the same as self-disclosure without context. The Netflix executive who shared his ketamine use at a company event may have genuinely believed he was modeling vulnerability. What he may not have accounted for is that vulnerability lands differently depending on the power differential between the person being vulnerable and the people witnessing it.
A CEO disclosing personal struggles occupies a very different position than a peer doing the same. The former creates an audience that feels obligated to respond supportively, whether they want to or not, and that can create its own form of psychological pressure.
Research by organizational psychologists has found that self-disclosure by leaders is most effective when it is purposeful, relevant to shared organizational experiences, and proportionate to the relationship. Disclosures that veer into personal territory not directly related to work—substance use, detailed health information, relationship dynamics—tend to make subordinates uncomfortable and can actually undermine the trust they are meant to build (Gardner and Avolio, 1998).
The Case for Substantive Over Performative Leadership
The most compelling material in Borchers’ article is not about what managers should avoid. It is about what they should do instead. Alyssa Pagoria’s approach is worth lingering on. She defines her effectiveness as a leader not by her ability to entertain but by her quality of attention:
- Weekly one-on-ones where she puts her phone away and gives her full presence to the person across from her.
- A refusal to abandon a struggling team member to a performance-improvement plan that most managers would have let run its course.
These are not flashy moves. They will not generate viral content. But they build the kind of trust that makes teams genuinely effective.
Gallup’s State of the Global Workplace report has repeatedly found that the single most important factor in employee engagement is the quality of the relationship with the immediate manager. Not perks. Not office culture. Not ping-pong tables or beer fridges. The manager.
Specifically, whether that manager is consistent, fair, communicative, and genuinely invested in the employee’s growth and wellbeing. The organizations that have internalized this finding have tended to stop designing elaborate culture programs and started investing instead in manager development—coaching people in the fundamental interpersonal skills that make the daily working relationship better (Gallup, 2023).
Stephen Courtright’s advice, quoted by Borchers, points in the same direction: focus on employees’ interests rather than your own image. This is a deceptively simple instruction that carries significant weight. A lot of what passes for culture-building in organizations is actually leader-brand-building. The boss who throws great parties is, at least partially, satisfying his own need to be seen in a certain way. The boss who helps an underperforming employee find her footing is doing something that has almost nothing to do with her own visibility. The distinction between those two orientations is not trivial.
The Humor Question
Borchers is careful not to argue that workplaces should become humorless. The Clean Comedians consultant Adam Christing makes the point that humor remains a valuable leadership tool—it just requires more thought than it once did.
Self-deprecating humor that does not punch at others, references to shared professional experiences, moments of levity that acknowledge the absurdity of organizational life—these can all build rapport without creating liability.
What the research bears out is that humor, when it works in professional settings, functions because it reduces tension and signals confidence, not because it shocks or provokes. Managers who rely on edginess for effect are usually chasing a reaction rather than building connection.
The two things feel similar in the moment but produce very different outcomes over time. A team that laughs together because someone told a smart joke about a familiar shared struggle is a different thing from a team that laughs nervously because the boss did something they were not sure how to respond to.
What Leadership Credibility Actually Requires
The broader argument that emerges from examining Borchers’ piece alongside the research literature is this: leadership credibility in the current workplace is built on consistency, competence, and demonstrated investment in the people you manage. It is not built on being liked, though being liked is a pleasant byproduct of doing the other things well.
Managers who chase likability as a primary goal tend to make decisions that are optimized for short-term approval and long-term instability.
The managers who have figured this out are the ones operating in what might be called a post-charisma mode. They are not colorless or robotic. But they understand that their job is not to be the most entertaining person in the room. Their job is to create conditions in which the people around them can do their best work.
That requires clarity about expectations, fairness in how those expectations are applied, attentiveness to the individual circumstances of each team member, and the courage to have difficult conversations rather than avoid them.
Those are not new ideas. But they are persistently undersupplied, which is why every new data point on manager effectiveness looks so similar to the last one. The managers who have your back, as Borchers concludes with quiet precision, are often cooler than the ones who are fun to be around. They are also, as it turns out, the ones who build the most durable teams, generate the most sustainable results, and stay out of the kind of headlines that end careers.
The rules of the game have not changed as dramatically as the anxiety-laden coverage of workplace culture sometimes suggests. What has changed is the tolerance for the gap between what leaders say they stand for and how they actually behave when the camera is on. Closing that gap has always been the work. Now it is simply more consequential to leave it open.