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‘Should I Give Up on My Dysfunctional Workplace?’

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Dear Boss,

I work for a medium-sized company that has recently grown its staff exponentially. Our company culture has always prioritized operating independently, and as a result, much of our staff (including senior executives, directors, and managers) is homegrown, with little experience working anywhere else.

Perhaps you can already see where this is going: We’ve gotten bigger than our existing infrastructure and expertise can support. We lack the processes, understanding, and protocols to work in a way that would be expected at any other company. Most of my 15-person team feels like there is no direction at all. We are often gaslit, instructed to do management-level planning (but then those plans are ignored or scrutinized), and the only solutions that are enacted or supported are the “simple” ones that they can understand. My work has never been reviewed, aside from the pedantic encouragement to “make things easier.” After years of working here, management honestly doesn’t seem to understand what we need to do our jobs.

This has obviously led to very poor morale, and several of us have talked of quitting. However, there was recently a glimmer of hope: Several staff, individually and as a group, spoke with the head of HR and made impassioned pleas for support. I have no doubt that HR understood the need for intervention, based on the emotions they showed while listening (which ranged from shock and frustration to outright tears) and the feedback they’ve provided since then. I’ve gotten the impression that they agreed that some sort of escalation was necessary. An outside consultant was one idea that appears plausible.

Aside from this gross mismanagement, this is my dream job. The pay is great for my industry and location, I love the field, I adore my company and its values. But I also have an opportunity to leave for a more traditional, boring, harder-working company. It would come with a pay cut. In short, I don’t want to leave, but I don’t know if I should stay.

When things are this bad and senior-level help agrees that something needs to be done, how much hope is reasonable? 

If you decide to stay, assume things will stay basically the same as they are now.

It’s not that companies don’t ever change. Sometimes they do. But the impetus for that needs to come from the company’s senior leaders; it’s very hard, if not impossible, to force this kind of change from below if top-level management isn’t fully bought in.

And that’s because they’re the ones who need to change. They’re the ones who have to do the (very hard) work of learning to manage differently, of creating new structures and practices, of setting the bar much higher than they have up until now, and probably of hiring (and then listening to) staff who may be more skilled than they are. They also might need to do the sometimes painful work of realizing that the skills that brought them this far aren’t enough to carry the company through its next stage of growth, and that they might need to bring in leaders who do have expertise and experience in managing a company of this size. But if they’re not fully committed to doing that work, it’s usually not going to happen. That commitment has to come from them or from whoever is above them, like a company owner, board of directors, or investors — people with the power to say “this must change” and then hold them accountable to doing that.

To be fair, some management teams do make that commitment, and they seek out competent help to guide them. And sometimes they come to that point because lower-level staff speak up and name the problems they’re seeing and demonstrate how it’s holding the company back. It’s possible that could happen here … but if things are so bad that your HR person is crying when she hears your concerns, I’m skeptical about your management team’s level of interest in and ability to do this work.

And it’s important to realize that the HR person herself does not have the power to fix these issues. She can explain what she’s seeing, and she can make recommendations, but ultimately it’s up to your senior leadership. HR is only as effective as they’re allowed to be by the management above them.

The same would apply to any consultant they might bring in. Consultants can do a lot to assess what’s going on — they can survey staff and speak to them privately, and they can observe, assess, recommend, and coach. And sometimes outside consultants’ recommendations carry more weight because they’re experts. But a lot of companies have consultants come in, identify serious problems, make compelling recommendations about what to change … and then little to nothing happens.

Again, that doesn’t mean that’ll be the case at your company. Your company could be one of the good ones that recognizes it needs more help. And there’s nothing wrong with giving it some time so you can get more of a sense of how likely that is to happen.

But until and unless you see concrete evidence of changes being made, I would maintain a significant amount of skepticism — because making serious cultural changes is both difficult and rare.

Meanwhile, though, you don’t have to choose solely between this job and the lower-paying job you’re considering! Why not job-search more broadly and see what else is out there? You have a job that you enjoy in lots of ways, so you have the luxury of taking your time with a job search and not jumping at the first alternative you find. See what your options are, assess them against your current job, and decide from there.

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every Tuesday.

‘Should I Give Up on My Dysfunctional Workplace?’