CEO enforces 'chaotic' work structure, employee's better alternative is rejected, everyone jumps ship: 'This isn't working out'

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Ben Weiss • Writer and Editor
Mar 2, 2025 2:00 PM EST

There is a reason why managers should take everyone's temperature on the team before instituting a policy. That way, you get a greater sense of how people may feel that procedures can be altered or made easier. That way, those at the top can have a greater understanding of what their team members are coming up against and whether or not their ideas should be adjusted to better fit their needs. 

Unfortunately, too many managers are too stubborn and self-absorbed to be able to internalize constructive criticism and empathize with the work experiences of others. This CEO clearly had zero interest in considering his team members' ideas before implementing what everyone, in hindsight, agreed to be a chaotic work structure.

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  • Thankfully, this employee was confident enough to suggest a direct conversation with the CEO, cutting the middleman so that they knew exactly what their boss wanted and expected from their work. Of course, the CEO did not seem to like this suggestion and wound up choosing his ego over what was best for the project. At the end of the day, it wasn't the employees who suffered because they all jumped ship just in time. It was the company that suffered the most.

  • 02
    I joined a startup's Al team, which consisted of just three people including myself, with the other two being more senior. We spent about a year developing a product that was gaining traction with new clients.
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    Then everything changed when our CEO decided that regular team-based sprints (basically once a day check-ins) weren't "effective enough." Instead, EVERY team member had to become a "head" of a project,
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    organizing, managing, and running separate daily scrums. Typically, each of us was assigned to 4-6 different scrums, completely destroying any sensible resource planning.
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    This was the breaking point for the two senior members in my team, who promptly decided to quit. I tried to stick it out, but the CEO started giving me sh** all of a sudden. I believe he was
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    holding a grudge because I once didn't answer my phone at 6:29 PM when work ended at 6:30 PM. I called him at 7, but apparently that wasn't enough.
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    The image does not depict the actual subjects of the story. Subjects are models.

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    After that, instead of talking to me directly, he would just speak to one of the seniors (who hadn't yet announced his resignation),
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    and that senior was supposed to relay that to me. But... he was ready to quit and wasn't really that helpful. And with the work management going nuts, everything was just going to sh**.
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    I mean.. engineering becomes if you don't know the intentions, but he just kept giving me tasks without an explanation. So I had a one-on-one with the CEO, and asked him to tell me what he wants directly.
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    This suggestion set him off. He implied that "this isn't working out," clearly suggesting my time at the company was coming to an end. Knowing what I knew about our codebase being built in Langchain and runnables
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    (notorious for their poor readability), and that, well, all of the members are quitting... Well, I liked this sub too much to let this go. About a week after receiving this message, the two seniors quit.
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    That was about a year ago. I now saw them putting out a news article, first PR they've done so far since I left. Yap, the entire project that we developed for about a year, gone and replaced with something completely new and generic. Can't say I'm not happy seeing that product crumble.
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    TLDR: CEO implemented a chaotic work structure that made two senior devs quit. When I suggested direct communication instead of going through a middleman, CEO implied I should leave. I complied, knowing our codebase would be impossible
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    for newcomers to understand. A year later, they've completely scrapped our promising product and replaced it with something generic and inferior.
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    KikiHou • 1d ago Not that I wish harm on people, but sometimes it's nice to see something fail after you haven't been treated well.
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    ratherBwarm • 22h ago I was a IT manager working with senior integrated circuit designers, creating world class cutting edge IC's.
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    I was present several times when the CEO called to ream out a designer for not being "on schedule". The schedule was an arbitrary time frame, because these guys were pushing the limits of our tech.
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    Turns out the CEO had over promised certain big customers, to stall them from buying parts from our competitors. I understand that's the game he had to play.
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    Belittling and browbeating these designers had negative effects. They could get jobs at any of the competitors for more $$'s. In several cases they did finish the design and left.
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workplace-stories toxic-manager work stories toxic-workplace job work Horrible Bosses company toxic-work-environment
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