Here we are again, another October, another round of corporate-mandated cheerfulness for Boss's Day, which brings with it all The challenges of showing appreciation on Boss’ Day. This year, the narrative comes pre-packaged with a particularly tidy statistic: a new GroupTogether survey reports that 75.9% of employees actually like their boss. It’s a clean, counter-intuitive number that neatly flips the script on decades of Dilbert cartoons and "horrible boss" movie tropes.

On the surface, it’s a comforting data point. It suggests a modern workplace where managers are seen as mentors and collaborators, not taskmasters. The top reasons cited are that they foster a “great team culture” (27.7%) and are simply a “nice person” (22.9%). These are qualitative, human-centric metrics. The data feels good. It feels like progress.

But my job isn’t to report on what feels good. It’s to look at the entire dashboard. And when I place that cheerful 75.9% figure next to the rest of the available data, the picture becomes significantly less coherent. In fact, it starts to look like a serious market dislocation between sentiment and reality.

The Disengagement Anomaly

Let’s get precise. While three-quarters of employees report liking their manager, recent Gallup data shows U.S. employee engagement has cratered to a 10-year low. Overall engagement fell to just 21% in 2024. Let that sink in. We have a situation where the vast majority of people claim to like their direct leader, yet an almost equal majority are disengaged from their work.

How can both of these things be true?

The dissonance deepens when you look at the managers themselves. A Kahoot! survey found manager engagement has fallen to a dismal 27%, with nearly half of all managers (a full 46%) admitting they would trade away their title just for a chance to feel engaged again. I’ve looked at hundreds of corporate filings and internal reports, and this kind of symmetric collapse in morale is a glaring red flag. You have a disengaged workforce being led by an equally disengaged managerial class, yet everyone supposedly likes each other.

This is where a simple survey question like "Do you like your boss?" becomes analytically weak. What does "like" even mean in this context? Does it mean you enjoy their personality? That they’re not actively hostile? It’s a low bar. Liking someone is not the same as trusting their leadership, feeling motivated by their direction, or believing they have your best interests at heart when corporate priorities shift.

The entire situation feels like staring at two charts on a terminal that are screaming different things. One shows a smooth, upward-trending line of personal affinity. The other shows a jagged, downward spiral in systemic health. An analyst's first instinct is to question the inputs. And the inputs here look suspect. A report from HR Dive found that 47% of employees feel pressured to be dishonest in engagement surveys. They fear repercussions or simply don't believe their feedback is anonymous. So, are people telling the truth? Or are they just giving the "right" answer about their immediate superior while their broader actions—and engagement levels—betray a deeper malaise?

The Fallacy of the Technological Fix

This brings us to the corporate response. Faced with a workforce that is both personally agreeable and professionally checked-out, companies are doing what they always do: throwing technology at the problem. The global Human Capital Management (HCM) software market is projected to grow from $35 billion to nearly $58 billion by 2029. That’s an annual growth rate of about 10%—to be more exact, closer to 10.4%.

This isn't just about payroll anymore. We’re seeing a massive wave of investment in AI-powered HR tools. Workday (NASDAQ: WDAY) is rolling out AI agents to screen resumes, cutting screening time by 57%. Oracle (NYSE: ORCL) is embedding AI into career-planning tools. The market for these AI assistants is projected to grow at a blistering 45% annually. The stock market is rewarding this pivot, with analysts setting price targets for firms like Workday and ADP that suggest significant upside (WDAY’s consensus target sits around $288, a ~23% jump from its current price).

This spending spree is a desperate search for a quantifiable solution to a human problem. The logic seems to be: if we can’t trust what our employees are telling us, maybe an algorithm can figure it out. It’s like trying to fix a failing marriage by installing more security cameras. The cameras will give you perfect data on movement and behavior, but they will tell you absolutely nothing about trust, resentment, or emotional connection. Companies are buying ever-more-sophisticated thermometers to measure the temperature of a patient who they already know is sick, but who they refuse to have an honest conversation with.

The investment in high-end office campuses with kombucha bars and golf simulators is part of the same flawed thinking. It’s an attempt to buy back the "employee connection" that remote work supposedly weakened. But connection isn’t a product of perks; it’s a product of psychological safety, shared purpose, and trust in leadership—the very things that plummeting engagement scores suggest are missing.

This Isn't a People Problem; It's a System Problem

The 75.9% "likability" statistic isn't a lie, but it is a distraction. It allows leadership to point to a positive number while ignoring the systemic rot. It individualizes a collective problem. People may very well like their boss as a person, even as they feel alienated by the corporate structure their boss represents. Your manager can be a wonderful, empathetic human being who is also powerless to prevent layoffs, advocate for a real raise, or protect you from burnout culture.

The data suggests we are not suffering from a crisis of "bad bosses." We are suffering from a crisis of bad systems. Managers are just as trapped as their reports, caught between executive demands and the needs of their teams. They are the face of a corporate contract that feels increasingly one-sided.

So, go ahead and celebrate Boss's Day on October 16th. Buy the card, bring in the coffee. But don't mistake personal fondness for institutional health. The numbers are clear: the ship is taking on water, even if everyone on board thinks the captain is a pretty nice guy.