Dear Businesslady: Can I Reform My Incompetent Managers?

First, a quick announcement: I’ll be doing a FREE professional development workshop through the University of Chicago Graham School on October 18th. The workshop is about managing your time and pushing back against unreasonable demands. You can attend in-person if you’re local to Chicagoland (there’ll be snacks!) or follow along online. Click here for details and registration info. Hope to see you there—especially if your job resembles anything in this month’s letter.

Hey Businesslady,

The core of my problem is: my managers are incompetent and I don’t know how to encourage a positive change.

I’ve been with my company for around 10 months now. It’s not in a field that I’m crazy about but I have my own responsibilities, can pursue my own projects, and have the potential to learn and gain a lot. My bosses have already paid for various classes/training for me and I’m generally busy rather than bored.

My two bosses don’t have any management experience, even though they’re highly successful. Communication is vague and I’m often left out of the loop on important issues just because they forget to tell me (e.g., they postponed an event I’d been planning). I will be handed projects with barely any background info—like cost negotiations without being told our budget. I find out about a lot of important decisions just by luckily overhearing in the office, otherwise I’m not told. On top of this there is a general air of incompetence around them; they miss client meetings, misread emails, repeat questions which I have already answered several times, and frequently blow deadlines when they’re not ignoring them entirely.

This is generally accepted (with some grumbling) by other employees and people that we work with, because a) for the employees we get a lot of freedom and also are paid well b) our managers are brilliant at what they actually do, just bad at all the logistics that go alongside it. (They’re also at least marginally self-aware, in the vein of “sorry I know we’re awful! lol!”.) But I am finding it increasingly frustrating. Because they’re so bad at processing information, I often feel like my ideas are wasted. I am always either picking up after their messes or chasing after them for small, simple tasks to get completed, instead of doing the process-improvement work I was hired to do—which obviously makes me feel very underappreciated and disrespected. Plus, I’m still relatively inexperienced and it’s demoralizing not to have any real mentorship.

A former colleague told me before she left that I put up with too much, but what is the alternative? Should I be more assertive with them? Are there some magical upward management tactics I don’t know about? Should I try to get over it: accept that I have to work with what I can get? Am I bad at my job because I can’t make them change?  

—Fed Up with Managing Up

Dear Fed Up,

It is an unfortunate reality of the professional world that people can become managers without being particularly good at being in charge of people—and that successful companies can be led by folks who are incompetent when it comes to basic business proficiencies. (The academia-specific corollary of this is that it’s possible to become a professor without ever holding an office-type job… or so I’ve heard.)

Additionally, it’s an unfortunate reality of… humanity that you can’t ever force another person to change. All you can do is to explain why you think it’s necessary, give whatever support you can offer, and hope for the best.

In your case, I’m slightly encouraged by the fact that they seem at least superficially invested in being good managers, what with all the paid training and autonomy you’ve been given. While that may not translate into a willingness to improve, I’m more optimistic than I’d be if they were tyrannical jerkfaces. At the very least, hopefully they can adapt to a few new habits. After all, they’re being profoundly inefficient in a way that can’t possibly be good for business, so it’d be to their benefit if they took your concerns seriously.

Before I dive in with suggestions, though, I want to emphasize: this is not your problem to fix. I’ve talked before about how a desire to go above-and-beyond can end up shackling you to an unmanageable workload. A lot of us have internalized the belief that our jobs should come before our personal lives every time, and disrupting that mentality is a huge part of my mission in offering career advice. It’s an issue for workers of every gender, but women are in an especially tough spot: we’re socialized to be accommodating, and if we manage to resist that conditioning, we’re often punished by people who expect us to be deferential. (I was already feeling fiery about this because I just started reading Feminist Fight Club: A Survival Manual for a Sexist Workplace, and recent news stories have not diminished my ire.)

All of which is to say: your colleague’s parting words strike me as a warning worth heeding. Coworkers who are headed out the door are often the best source for honest truths (with the exception of flagrant shit-stirrers or otherwise unreliable narrators). So please keep her message in mind, both while you’re figuring out how you want to handle this and once you put your plan into action. If you decide to throw up your hands and let Goofus and Doofus run their company into the ground while you find another job, you have my blessing. But in the meantime, you might as well try to mitigate their ineptitude.

The first step in that process will be showing them how incompetent they are (although obviously you won’t want to use that particular word). They know they’re terrible—and apparently are hoping their staff will find it charming—but do they really understand the cumulative effects of their consistent flakiness? Here’s how I’m betting it goes down: a self-inflicted crisis emerges, you and your coworkers jump into damage-control mode, and since they’re the ones in charge you know it’s not appropriate to express your frustrations about it. Then it subsides and everyone catches their breath before the cycle repeats itself.

It can feel uncomfortable to interject A Serious Meeting into an otherwise calm period at work, but if you wait for what feels like the perfect moment, you’ll be waiting forever. Start getting ready for that conversation and then seize the first opportunity to have it. You need to establish that this is a pattern and that it’s causing problems—for you and for your colleagues. Fortunately, your job is to improve their processes!

Sit down with them and share the good news: you’ve figured out how to make things run more efficiently around here. Share examples of times when their missteps have had real consequences—dissatisfied clients, lost profits, unacceptably sloppy last-minute work. Then explain your plan for preventing those missteps in the future. If they express surprise (“you should’ve said something sooner,” “this is coming out of nowhere,” “we’re so sorry!”) shut that down with some version of this verbal mic-drop: “I’ve been thinking about this for a while, but I didn’t want to bring it up until I could offer some concrete solutions.”

What might those solutions be? I have a few ideas.

My first diagnosis is that these amateur-hour CEOs need an assistant—it’s not your job to keep them on track, but it could be somebody’s, and that person could solve a lot of these basic organizational problems. (It would also help rule out “why don’t you just nanny us” as a potential cure for their disorganization.) Unless that’s already been ruled out as an option, you should suggest it and see if you can get them to agree.

You should also be having regular meetings with them, assuming you aren’t already—ones that you reschedule ASAP if they get blown off. You can use this as a chance to ask for input on your projects, nudge them about outstanding tasks, and learn what’s going on around your office. (They’re forgetful about updating you proactively, but one hopes they’ll respond to direct questions if you’re sitting there in front of them.) If you need info that they can’t provide during the meeting, make a note of it and set a deadline for when they’ll get back to you. Yes, I know, deadlines are meaningless to them, but that will at least give you license to hound them for the answers they promised.

Because you probably will have to hound them—especially while they’re still adjusting to this novel new concept of “being halfway decent managers.” That’s part of why a A Serious Meeting is necessary: you need to explain that you’re about to change your own behavior (even though the end goal is to provoke a change in theirs). From now on, if you’re waiting on something from them, they’re gonna know about it. You should remain as polite and collegial as ever, but don’t let them laugh things off or dismiss you with “I’ll tell you later.”  Someone needs to hold them accountable, and since you’re the one who wrote to me, I’m deputizing you to keep them in line.

Of course, you’re not alone in this office, and surely you’re not the only one who’s losing patience with your bosses’ antics (not counting the ones who got so demoralized they left for other jobs). As part of the prepwork for your new transformative plan, poll your coworkers: what issues are causing them the most aggravation, and what process improvements would they recommend? You don’t have to make a big deal about it either—just let them know you’re planning to propose some changes to make your lives easier and ask if there’s anything they’d like to suggest.

On your side of things, start keeping a master list—or maybe several lists, depending on your workflow—of everything within your purview. Have a record of every deadline, every piecemeal component of a larger project (with associated sub-deadlines as needed), and every detail that needs CEO approval. Update it like it’s your religion. That way, at least someone in the company will be aware of what the current top priority should be.

I know their email comprehension isn’t great, but nevertheless, you might find it useful to send them a weekly digest (Friday afternoons? Monday mornings?) with the highlights of what they should be focusing on. Keep it simple and short so that they can’t get distracted halfway through reading it or misinterpret anything—think bullet points, dates in bold.

Finally, this whole dual-CEOs thing is an unusual setup, which may not be unrelated to the general sense of chaos conveyed by your letter. Is there a clear division of labor between them, or are they constantly like two people struggling to go through a doorway simultaneously? Is there a bottleneck happening where they both have to weigh in before anything can get done—and if so, is that really necessary? Try to find a logical way to divvy up their responsibilities or, barring that, a system for streamlining their respective involvement (e.g., “Goofus works with marketing on brochures and Doofus approves them before they go to the printer”).

It sounds like this company started as two dudes with a shared talent/product/whatever, and that they haven’t acclimated to the fact that it’s not just about them anymore. If they’re truly invested in the work they do—and in their employees’ professional development—they should be grateful for instructions on how to to do better.

Your job is to show them what needs to be done, and if they won’t do it? Not your fault, and eventually, not your problem. Just make sure you find less-dysfunctional pastures before this position irrevocably warps your sense of what’s normal.

Businesslady is an editor, writer, and the author of the “witty and entertaining” career guide Is This Working? She also has a monthly-ish TinyLetter, so subscribe if your inbox can handle another one. Got a query of your own? Email

Recent Dear Businesslady columns can be found here, and the deep archives are here.


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