Dear Pooja: My boss sucks. How do I deal?
Comparing the two kinds of bad bosses.
Hi folks! Welcome to the first edition of Dear Pooja, a monthly advice column where I’ll answer your questions about life, mental health, and navigating real self-care. I’m kicking things off today with a question about dealing with a crappy boss. To submit your own question that I might answer in the future, just reply to this email, or email me at pooja@poojalakshmin.com with the subject line DEAR POOJA.
Dear Pooja,
I’m in my 40s and work in corporate America, and lately, my boss has been making my job miserable. She micromanages everything I do and is super vague when giving directions. One minute she wants me to be more proactive, but when I am, she criticizes me for not following her (unspoken) expectations. I feel like I’m always guessing — and always wrong.
For example, last week I stayed late to finish a project she said was a "priority." The next morning, she told me I should have waited for her input before completing it, even though she hadn’t mentioned that earlier.
On top of that, there’s constant pressure to be available 24/7, and if I’m not, I feel guilty. I’m exhausted, burned out, and it’s starting to affect my family and sleep. But I can’t just quit; I’m well-paid, one of my kids gets therapy covered by my insurance, and I have a mortgage to think about.
So, here’s my question: Is my boss just clueless, or is she actually a narcissist trying to make my life hell? And either way, how do I handle this without making things worse?
Sincerely,
Burnt Out and Confused
Dear Burnt Out and Confused,
I love this question. As I’ve been interfacing more with corporate America over the years, I often get asked about workplace issues like how to deal with a terrible boss, or if one should leave a job.
But, your question gets to the heart of what anyone who works in corporate and has a difficult manager should be asking themselves first: What kind of bad boss do I have?
First, there’s the well-meaning yet clueless boss who has never had management training and doesn’t know what they’re doing. Second, there’s the boss who has been around the block, is aware of where they fall short, and has zero interest in changing their ways. It’s important figure out which one you have, because the prescription for how to deal with each is quite different.
The well-meaning but still bad manager is someone who is open to feedback (if delivered in an appealing manner) and generally feels like a reasonable person. This is a manager who is probably early- to mid-career, and was likely thrust into a management role without any leadership experience or training. Working for these types of bosses is a little bit like dating a guy who has never had a girlfriend before. Essentially, you are training them to be a better communicator and learn how to delegate effectively. It’s a lot of “managing up” and emotional labor on your part as the employee. And, usually, it’s their next direct reports who benefit from the hard work that you put in.
I’ll admit that I have been in this category; it’s only in the past couple years that I have been in a management/executive role, and it has tested my organizational and leadership skills. There have been several times a direct report has pushed back on a request that I made, saying that the timeline I asked for was too quick or that I didn’t give clear enough directions or information. Each time that happens, at first I feel guilty and beat myself up, but soon after, I am grateful for the feedback and ready to improve. The boss I am today is different than who I was six years ago when I started my private practice, and I intend to be a different (and better) boss six years from now, too.
Then, there is the genuinely trash boss, the one who is perhaps a little more seasoned and has received the feedback that they need to work on their “bedside manner,” as we say in medicine — and they just do not give a fuck. This is a person that flies off the handle when you try to set a small limit. They are not able to slow down to reflect or be self-aware, and they show a pattern of disinterest, disrespect, or a lack of integrity. If you have this type of person for a boss, you will not be able to teach them. This is the fuckboi version of a boss: they will not learn, and any time you put into trying to change them is a waste. More importantly, the longer you spend with them, the more your mental health suffers.
DIAGNOSE YOUR BOSS TYPE
Reflect on these situations and identify how your boss might respond:
You go to your boss with a systems-level complaint, perhaps about an inefficiency in workflow or a need for extra support.
A trash boss: will find a way to turn the conversation into a criticism of your work product, your working style, or you personally. They will not acknowledge the issue as a real, systemic problem and instead ask you to work harder. You will leave this conversation feeling confused and second-guessing yourself.
A clueless boss: will likely name the external reasons that it can’t happen (no money, downsizing, not a priority, etc.), but will not gaslight you into thinking that this problem is only in your mind. You will leave this conversation feeling frustrated and, perhaps, feeling powerless.
You express a small boundary.
A trash boss: often has a highly emotional reaction, taking your boundary as a personal affront. If you enforce the boundary, they follow up with direct or indirect retaliation. You feel scared when you leave this conversation.
A clueless boss: will become alarmed and more stressed/nervous themselves. They might say the wrong thing or push back in a way that is reactive, but they will not be retaliatory or threatening. You will leave this conversation feeling annoyed and overworked.
You go through a difficult personal situation (eg. a death in the family or sickness).
A trash boss: may feel unsafe to even share this information with. If you do share your situation, they will appear annoyed and irritated. This type of boss will continue to expect that you perform despite what’s going on in your personal life, or they will punish you directly or indirectly for not being able to put in 100%. You will feel like you are being punished and you may feel scared.
A clueless boss: will genuinely feel empathetic for your situation. They may send flowers or a note to express their sympathy. However, once they become overwhelmed with the demands on their own desk, they might send you a panicked messages asking about when you will be back, or put demands on you that are not sensitive to your situation. You will feel guilty about taking time away, and worry about the load on the rest of the team.
HOW TO DEAL
If you now know that you have a trash boss, first of all, I’m sorry. Next, you need to start strategizing how to get out of their orbit of power. Trash bosses will operate in a pattern that is similiar to the cycle of abuse: tension building, blow-ups, honeymoon phases, and periods of normalcy. This cycle can continue for years, but it’s important to know that a trash boss will not change. And you can’t begin healing from a toxic workplace experience until you are safely removed from their sphere of influence.
Your new goal is to develop a Plan A, B, and C for how to remove yourself. These escape routes could include building a case to be transferred to a different internal team, starting a job search, and, eventually, leaving the company entirely.
How do you deal with the trash boss in the meantime?
Set firm boundaries. Minimize contact as much as possible, avoid chance encounters, and keep all meetings scheduled so you can be emotionally prepared.
Find your allies in the office. You need to have people around you who understand your situation and can be supportive.
Do your best not to internalize any “feedback.” Get a therapist, a coach, or a support group to help you process your trauma.
But what about if you are dealing with a clueless but well-meaning boss? This is tricky because it’s impossible to predict how long it will take for your boss to learn how to be an effective manager, and in the meantime, you will be doing a ton of emotional labor to manage up. However, managing up could help you achieve more of your workplace goals in the meantime.
Ultimately, the clueless boss is one who needs help with decision making and delegation. The way for you to handle this is to OVER communicate, even when it feels tedious (it probably will), because this forces them to give you direction.
How do you deal with a clueless boss?
Develop strategies to manage up. Ensure you have weekly 1:1 time with your boss, take ownership of the agenda (ie. direct the conversation to what you want to talk about), and make sure your job description and responsibilities are crystal clear to both of you (that way, you’ll easily be able to call out when you’re asked to do something that’s not your job).
Develop a direct communication style. Get comfortable with regularly reporting task progress and achievements to your boss, and don’t be shy about following up with them about their responsibilities that affect your ability to get your job done (aka “Did you make the final edits on tomorrow’s slideshow? I need them so I can be prepared.”) Always ask: “What would you like me to prioritize?” This helps remind your clueless boss that your time is not limitless.
Get hyper-organized. Keep meticulous notes on calls and conversations you have with your boss (and keep priorities and directives in a shared space, such as email or the company chat.) That way, when you get an ask that feels out of left field, you can follow up with something like, “Last week you mentioned you wanted me to focus on X, so I completed Y, but then today you said I should do A. Which task do you prefer I should focus on?”
It all boils down to this, Burnt Out and Confused: A clueless boss is one who is likely overwhelmed with what’s on their plate and preoccupied with their own responsibilities, so they need some gentle reminding on how to steer. A trash boss is one who gains energy from making people on their team feel little or less than. Learning which is which is a muscle that is worth developing and will serve you for years to come — and help you know when to stay or leave a job. Run through these example scenarios and see how they unfold. Once you do that, you should have your answer.
xo,
Pooja
Bonus: I love this Harvard Business Review piece by my friend Deepa Purushothaman, author of The First, the Few, the Only: How Women of Color Can Redefine Power in Corporate America, about how to heal after a toxic incident at work. The process Deepa describes is similar to what I help my patients work through in therapy.
Wow — thank you for this! I recently extracted myself from a trash boss after about a year and a half of trying to make things work. Unfortunately, I experienced this boss reacting in all of the ways you used as examples and did indeed see my self confidence diminished. It’s helpful to see this all laid out so clearly, thank you.