how to confront your boss

a guide to boundary-setting and self-advocacy for the conflict-avoidant

Welcome back to Of Counsel, my monthly advice & asks column. If you ever find yourself wondering, “What would Cece do/think?” then you’ve come to the right place! You can find previous columns here and submit questions here. And if you appreciate the work that goes into this newsletter and want to help ensure that my educational and informational content remains free for all, you know what to do!

My body is OOO in Albania and Spain, but my mind is always still at work. 🙃

Hi Cece,

I struggle with speaking up for myself at my nonprofit workplace. My manager is passive aggressive, does not advocate for me, and underestimates my capabilities. I am saddled with responsibilities above my job description (wearing many hats as nonprofits demand) and feel undervalued by my manager. I love the work and all of my other colleagues, but I rarely see them and have to work closely with my manager. I've been advised to either privately talk to my manager to let her know how I'm feeling to ask her to change or tell our HR that I'm unhappy. I'm struggling to determine if it's even worth it to use my emotional energy to try to advocate for myself or just look for a new job. I really struggle with setting boundaries and verbally stating out loud when I am uncomfortable or unhappy. I suppose confrontation is inevitable, so any insight how to prepare for that so it feels less awful before, during, and after the conversation? What would you do?

- Anonymous

You have the right idea! If you’re at the point where you’re thinking about looking for a new job, you might as well throw a Hail Mary and see how it goes. It’s also fantastic real-life experience with confrontation and direct communication—skills that will be invaluable going forward not just in the workplace, but in your relationships, family dynamics, friendships, etc. You can’t buy this sort of applied experience, so my vote is to muster up the emotional energy to advocate for yourself—and learn about yourself and workplace negotiations while you’re at it.

Like you, I am naturally conflict-avoidant.¹ Instead of saying how I feel or what I want, I’d rather spend a week compiling a dossier on someone and then “casually” bumping into them and finding the perfect moment to “mention” something I’ve been thinking of that—oh, hey!—they might be interested in. This tactic works brilliantly for many workplace scenarios; unfortunately, it is a disaster for setting boundaries and advocating for yourself.

So how to go about it? I like your framework of before, during, and after, so let’s talk about what you can do at each stage to develop this very important life skill.

Before

In any confrontation, preparation is key. The more you prepare for the conversation beforehand, the less awful you’ll feel during and after. (Of course, don’t needlessly perseverate—that’s just giving into anxiety.) Preparation will help you familiarize your own wants and needs to yourself, as well as ensure that those wants/needs can be communicated in a firm (but still gracious) manner.

I’d undertake the following steps:

• Think about specific changes you’d like to see. Would you like more of X work and less of Y? Monthly check-in meetings with your manager to discuss your career advancement and opportunities they can put you up for? Fewer passive aggressive emails that present as questions but really are just demands? Write all of these down. Then ask yourself: if most of these happened, would you be happy to remain at your job? If no, then brainstorm more specific changes you’d like to see. What would it take for you to be, at the very least, content with your job for the foreseeable future?

• Translate each specific change into a talking point. One of my favorite parts of legal work is coming up with “talking points,” i.e., sentences that perfectly straddle the line between truthful and anodyne.
  
  As easy as it would be to tell your manager, “I hate it when you send me passive aggressive emails,” I’m gonna go out on a limb and guess that won’t go over well. Figure out how to rephrase each change you’d like to see as a talking point which isn’t trying to assign blame, criticize, or deflect—focus instead on the neutral, actionable task underlying your complaint.
  
  The passive aggressive emails point can become, for example, “I’d like to better understand the big picture of our projects. Could we have a quick call at the beginning of each project to discuss what needs to happen at each step and why? That would help me take greater ownership and be more effective.” Or maybe the passive aggression is due to your manager’s own micro-managing anxieties, in which case the talking point can become, “I’d like to establish a regular check-in cadence for our work together. It would help ensure, and give you assurance, that I’m on the right track.” The key is to remember that you have aligned goals and translate your issue into something that is mutually goals-aligned.
  
  One of my author friends reminded me recently that everyone’s goal in publishing is the same: Get rich, get famous. I can romanticize the ~artistry~ and ~beauty~ of writing all I want, but at the end of the day, I need to translate whatever I want into something that makes sense for the shared goals of getting rich and famous. Put another way, I can’t go into a meeting speaking English when everyone else speaks Japanese.

• Prepare conversational off-ramps. Confrontations can be conflict-ridden, but they don’t have to be. Still, you can’t predict how your manager will respond, so it’s good to prepare some conversational diversions or off-ramps in the event things get too heated. If they try to bait you or turn it into some sort of blame game, you can say something like, “Thanks for sharing. Let’s definitely discuss that in the future. For now, I’d like to focus on the topics I prepared, if that’s all right.”
  
  And if they continue having a meltdown or making it personal, you can end the conversation with a polite, “Thanks for listening. Let’s continue this conversation another time, after we’ve both had some time to think through things a little more.” (Although the writing is on the wall at that point… time to dust off the ol’ resume.)

• Practice the talking points with a friend. The same way we conduct mock interviews to prepare for job interviews, conduct mock confrontations. The idea behind both is the same—we want something (the job or specific changes in the workplace), and we need to effectively communicate that desire. Describe for your friend as best you can what your manager is like, and practice giving your talking points to your friend, with them interrupting or trying to bait you or making it personal, however you think your manager is likely to respond, and using that opportunity to practice the conversational off-ramps.

• Create a plan for when and how to begin this discussion. Do you have an upcoming meeting with your manager that you can bring this up at the end (and which would leave enough time at the end to fully discuss)? Do you need to email your manager separately about wanting to catch up? There’s no right answer here—it’s dependent on how you’ve interacted with your manager thus far and what you’ve observed about when they’re at their most attentive and receptive.

During

I like to take 15-20 minutes before high-stakes conversations to listen to music and read through my talking points. It’s perfectly fine to take your talking points into the meeting and refer to them during the discussion. (You can even say something like, “I made some notes ahead of time and want to make sure I’m covering everything.”)

To begin the conversation, I’ll say something like, “Do you have a few minutes to discuss my work?” or if it’s already a separate meeting, I’ll thank them for taking the time to meet with me after ~5 minutes of niceties and segue into saying I wanted to talk to them about something specific. Then I launch into the talking points.

By now, hopefully all the prep in Before makes the confrontation feel less awful during. Your only goal is to stick to the talking points. Trust Past You in preparing Present You for this moment. Don’t veer off-script. If anything goes south, you have the conversational off-ramps. You’re in control, and you’ve got this.

My favorite example of sticking to the talking points is a situation I read about in Adult Children of Emotionally Immature Parents by Lindsay C. Gibson. A man’s mother is living with his family, and she’s proven to be difficult—constantly criticizing not just him but also his children. The man must tell his mother that she needs to move out. When he does, she responds with guilt: How could you do this to your own mother? Don’t you love me? I knew you never loved me. The man must stick to the talking point—the neutral action that he is advocating for—despite his mother’s baiting. The book recommends something like, “I do love you, Mom, and the kids do, too. However, you can’t live with us. I’ll help you find another place to live, but it can’t be here.” It’s a wonderful exemplar of self-advocacy even in the face of heightened emotions. (And in case you’re interested, the entire book is a great exercise in setting boundaries and advocating for yourself in the emotionally-laden context of family.)

After

You did it! Try not to immediately conduct a post-mortem and pick apart every minute and where it could have gone better. There’s time later for that. Treat yourself to 15 minutes of something you love as an immediate reward—walking to Salt & Straw for ice cream, scrolling TikTok, whatever—and pat yourself on the back for having done something emotionally hard. You deserve it. (If it went poorly and you want to cry, let yourself cry—or call a friend and cry to them.)

For the rest of the day, try to go about life as normal. Do your work, go to the gym, see a friend. You’re still too close to the confrontation to be truly objective about what happened.

Whenever you’re able to think about the conversation without an overwhelming claustrophobia of cringe—maybe it’s the next day, maybe it’s in a week—that’s when you can tackle the post-mortem and think through what went well and what could’ve gone better. This won’t impact the situation at hand; it’s more to garner self-knowledge about conflict and confrontation for the future.

And then you wait! See how your manager responds. Will they see your point and implement those changes? Will they become even more passive aggressive? Because you were deciding between having this confrontation and looking for a new job altogether, you should already be prepared for all outcomes. Whatever happens, rest assured that you tried your best—and also honed a very valuable life skill.² ◆

Thank you for reading debrief! If you enjoyed this post, consider upgrading your subscription or sharing this post:

Becoming a paid subscriber gives you access to my inner sanctum—essays and private podcast episodes on nascent ideas—as well as archival posts older than six months. Subscribing also helps ensure that my informational and educational video content on all other platforms remains freely available to all.

Please know, though, that having you here and being able to be in conversation with you is the most important thing to me. If you are a student without disposable income, un-or under-employed, or a minimum-wage worker, just email me or fill out this form and I’ll comp you a free subscription, no questions asked. If you’d like to donate one of these subscriptions, you can do so here.

1. Apart from any situation with my parents, in which case I become conflict-seeking…

2. Whenever I ask my MBA friends what the most important skill they learned in B school was, they will invariably say, “How to have difficult conversations.”