Millennial managers are under fire for trying way too hard to be the 'cool boss'

• A TikToker went mega-viral with his impression of a laid-back millennial manager.
• People argued that the perceived desperation to be a "cool boss" is actually damaging.
• But the criticism of millennial management may be a bit unfair, experts say.

Millennials are under fire again. This time, for the management traits one creator has associated with the generation.

Last week, a comedy TikToker who goes by Rob posted a video with the on-screen caption "POV: You have a Millennial manager."

In the clip, he played the part of a manager in a meeting with an employee, putting on an overly familiar and self-consciously casual persona.

Here's how it went:

• He began by appearing to join the meeting frazzled, while still eating lunch, then scoffed altogether at the concept of their monthly catch-up. "These are just as annoying for us as they are for you," he said.

• He seemed to encourage the employee to stick to their working working hours, insisting they shouldn't reply to emails after hours or when they were out sick.

• The manager admitted to running personal errands on the clock and said his employee could pick up their child from daycare during office hours too, and he would cover for them.

• He then told the employee they didn't have to clear their vacation request through the official portal as he had already OKed it, and described another worker who insisted they do so as "annoying" and "a kiss ass."

• At this point in the meeting, the "millennial manager" became distracted by a meme he'd received from another worker, which he said he would forward to the employee, and wrapped up the meeting.

The video blew up with 10 million views and over 21,400 comments, many from people who said they had a millennial manager similar to this, and it made their working life much easier as they felt relaxed and supported at work.

Many self-described millennial managers also seemed to identify with the behavior, saying they tried not to pass down any negativity to their workers.

But it wasn't long before the tide turned.

On January 12, the TikTok was re-posted to X, formerly Twitter, by a user who wrote they could relate to it too. The video blew up once again, this time with 14.6 million views, and while many continued to praise the approach, others were less enthused.

Viewers began calling out the casual approach to management

As the video continued to circulate, people began to call out some of the behavior depicted.

One user wrote "these types of managers are the worst" and suggested they created "a false sense of warmth" and would ultimately stab employees in the back.

Another, who said they were a former supervisor, echoed this sentiment, and suggested some managers tried too hard to be seen as laid back by their employees, but would ultimately report everything back to the higher-ups. The post received over 20,000 likes.

People said managers like this were counterproductive, creating chaos by ignoring procedures and causing anxiety due to unclear expectations. Others suggested they would rather have a manager from an older generation who may care less about them, but made sure the work was done correctly. They were called smarmy, fake, and even toxic.

The verdict seemed to be in: "millennial managers" are the worst. But it may be more complicated than that.

While not all millennial managers behave this way, the skit isn't completely off base

Vivek Iyyani is the founder of leadership training organization Millennial Minds and author of "The Millennial Leader," which examines how different generations take on leadership roles in the workplace.

He told BI in an email exchange that while the idea of a "millennial manager" in the video is based on a stereotype, there is a clear generational divide with managerial methods, and the traits displayed in the video are "more visible" among younger generations in these positions.

"This leadership management style resonates much more with the younger millennials and Gen Zs and I believe we will see more of this approach amongst this group compared to the older millennials, Gen X, or baby boomers," he said.

Christopher Littlefield, the founder of Beyond Thank You, a business consultancy and management coaching company, told Business Insider there's nothing new about leaders trying to be seen as "the cool manager" like the character in the viral video, although the way people strive to achieve it has shifted.

"Talking about mental health, checking in about people's wellbeing, is not necessarily things that people did maybe in other generations, and it's more common now because it is a societal conversation," Littlefield said.

The manager character in the script isn't all bad

Littlefield said the depiction of a manager in the video does a good job of showing their "humanity" by connecting to the employee on a personal level, checking on their health, and ensuring they're not overworking.

But they fall down when trying to bond with the employee by turning against the company, its policies, and other members of staff. This could backfire and create a sense of distrust, and lead employees to believe they don't need to follow company guidelines either, he said.

It's a positive move when managers take the time to check in with workers, remember things they're worried about, share memes, and joke around, as long as the overall professional boundary is maintained, Littlefield said.

No one style of management can be completely associated with a particular generation, but the topics the parody touched on are indicative of a generational change in the workplace, Littlefield said.

In recent months, Gen Z and millennials have called for more flexibility with their jobs, and a greater emphasis on a work-life balance, BI previously reported.

Iyyani told BI that he thinks some aspects of the "millennial manager" stereotype may actually be welcomed by some workers.

"While I won't daresay all millennial managers have this approach, this sure seems to be the desired change on the ground from leaders. Someone who is respectful, protective, and engaged with the team," he said.