Skip to main content
By the time I arrived at work, I was in control of myself, focused, and ready to rip throats out.

My Secret Weapon for Preparing for Awkward Boss Confrontations

I’ve had a lot of uncomfortable discussions with bosses. A few things I’ve told them that come to mind…

“You deliberately humiliated another employee on a group call, and that level of immaturity and pettiness is professionally unacceptable.”


“Your administrative assistant, whom you love like a son, says casually and openly racist things whenever you’re not in the room.”


“You need to pay me $20,000 more dollars.”

To be fair, I said that last one nicer. And I had some great PowerPoint slides to go along with it!

Unlike a lot of people, I am actually very comfortable with conflict. I would even say I thrive on it. (There’s no way to say that and not sound like an asshole, but I am what God made me: an ENTJ.) Of all people, I probably go into a confrontational situation with the least possible amount of anxiety.

Nevertheless, I need extra deodorant on those days. My hands shake. My voice trembles. Which I really, truly hate. It makes people think I’m nervous, when it’s more of an under-exercized-border-collie-looking-at-a-fat-city-pigeon-and-trembling-with-overwhelming-herding-instinct situation.


Having a difficult conversation with your boss is really hard. They’re often terribly high-stakes. Depending on the nature of the conversation, you may feel like you’re ambushing your boss with new and unpleasant information. Your life and livelihood may feel like they hang in the balance. It is not easy to stay chill.

That’s why I have a secret weapon for going into such conversations.

If music be the food of fucking crushing it, play on

Music has an incredible capacity to direct our moods. We’ve known this since at least the time of Plato. (And Dexter’s Laboratory.)

There’s lots of science behind this. A moderate amount of background noise promotes abstract thinking and creativity. Music training is also positively correlated with an increase in both vocabulary and nonverbal reasoning skills. Listening to music also helps an athlete override their body’s fatigue signals, allowing them to push further—despite needing 7% less oxygen overall.

I am a huge believer in the pump-yourself-up playlist. I created my first one when a friend was pushing me to give a guy my phone number. (To be clear: I have given a man my phone number exactly once in my entire life. He did not call. NO RAGRETS.) I pretty much knew that the outcome wasn’t going to be what I wanted, but my friend recognized that I almost never did things unless I knew success was assured—a fact that makes me great with money and bad at dating smoking hot people. Tempting failure is a surprisingly important life skill, so I went along. My playlist (titled “CONQUEST!!!1”) was invaluable in shoring up my nerve.

*Hacking cough, hacking cough* I am now in the twilight of my life, an ancient crone of thirty-one years, and I’ve been married for a while now. My husband is pleasingly-yet-not-garishly attractive. But the trick of psyching myself up with music has worked ever since.

Boss fight music

In video games, there is often a regular song that plays during regular fights, and a special boss theme played only when confronting major bosses. I stick to this strategy, and have earmarked a certain song from my library to only play when I’m pumping myself up to have a difficult boss conversation.

What is it? Hmm, well, it’s a secret. But we’re all friends here. It’s Kiryuin Satsuki’s theme from Kill La Kill.


(One of the finest anime ever created, only one season, and it’s on Netflix. Go on, you know what to do with all of that information.)

It works really well for me because it sounds like the soundtrack to a military parade thrown by an extremely competent narcissist. And no, that’s not a dig at Donald Trump. I said competent! Before my last awkward boss conversation (“my work assignments suck and you’re too junior to manage me”), I trumpeted this song on repeat for the drive in to work. By the time I arrived, I felt in control of myself, focused, and ready to rip throats out. Our talk was successful, and I came out of that meeting with a new boss and better assignments.

This song ain’t necessarily gonna work for you. One of the amazing things about music is that different genres light up different areas of our brains on an individual basis. There’s something out there that will make you feel the same way. You just have to find it!

Asking for a raise, requesting a change of assignments, confronting bad culture… that shit is intimidating. Do you have an awesome song that pumps you up to to face these bosses? Tell us about it in the comments below! Because I am 100% going to burn them all onto a mix CD to listen to in my car, here, in the year 2003.

14 thoughts to “My Secret Weapon for Preparing for Awkward Boss Confrontations”

  1. Hahaha! I was not expecting that tip at all. Great article! I’m AWFUL at confrontation. I just want everyone to like me, damn it.

    It has gotten me nowhere in life to be a doormat, and guess what! People still don’t like me.

    1. Isn’t it amazing how that works out? It goes back to my whole McDonalds Napkin Theory of the World. If you’re always there and always free, people grab you by the fistful and use you recklessly.

  2. I don’t know that I have a pump-up song for this particular purpose, but I do have a playlist that I use for running (or dancing around my house). It is strictly women artists only and features songs like “Bombastic” by Bonnie McKee, “Boys Wanna Be Her” by Peaches, and “New Rules” by Dua Lipa among others. I have recently added “Make Me Feel” by Janelle Monae.

    The worst and most uncomfortable boss conversation I ever had: I had to report an incident of really blatant office bullying where a co-worker with whom I had an up-til-then minor personality conflict with had berated me in front of half our unit for not phrasing something to her liking. After that day, the co-worker was constantly gossiping about me – questioning why I took “so many” sick days and that I got to go to conferences that she wanted to go to (uh, I wrote a very detailed proposal and applied for a grant to subsidize the cost?) . When I first took it to my boss, my boss was very kind and admitted that she had “noticed” some of the inappropriate behavior from my co-worker. I got a really brief apology note from the co-worker and then two weeks later, an unprompted raise. However, the bad behavior continued. It was months before I brought it up again and again, I was met with polite placation. I waited for something more to happen, but at this point, I was basically just getting the cold shoulder and was increasingly miserable at work. I started looking for other jobs. I got one fairly quickly and took it blindly – it was basically a side-step to another agency with no change in salary, but I was desperate. When I told my boss, she was weirdly devastated. She then went to another co-worker of mine who had also reported instances of bullying (although not as extreme) and basically fell over backwards to say that she wanted to do anything she could to help *her* out. It was like a final slap in the face.

    This happened to me fairly early in my career and I’ve been cagey about making friends in the workplace ever since, although I’m coming out of my shell a little more these days. I’m glad it happened when I was young though, because aside from the job I took out of immediate desperation which turned out to be a bust – I learned a lot of valuable lessons about evaluating how a workplace fits with me personally and what kind of bosses I want to work under. I also take comfort in the fact that while I have moved way up the career and salary ladder, that bullying co-worker is still in the exact same position with the same ol’ salary. (So I guess……maybe she did me a favor after all by forcing me to spread my wings?)

    1. All of those songs are fantastic. Gotta respect the teaches of Peaches.

      My general rule is to not become friends with coworkers. I keep it profesh. At every workplace I’ve been in, 1-2 people still manage to worm their way into the dusty, dried-out apple of my heart, which is doubly-lovely because I’m not looking for it. Tight friendships make for future cliques, snubs, gossiping, bullying, hurt feelings, etc.

      The situation you describe is pretty shitty, but also pretty typical. I quit a dream job, in a dream location, with a dream salary, and dream team members because the culture was fucking rotten. Sadly, I think the only way to appreciate how important culture is is to be stuck in an environment with a shitty one. It’s good you got it out of the way early.

  3. Time to admit the embarrassing truth: if I need a confidence boost for any work related stuff and difficult conversations I listen to Carrie Underwood’s Choctaw County Affair. DON’T JUDGE ME OK?!?!

    If it’s time to Get Shit Done at work I put on The Planets by Holst and I put them on loud. And I mean LOUD.

    And if I need to at least pretend to be a functioning human being before a meeting, I go old school and put on Working 9 to 5.

    1. I have such nice memories of The Planets! I played timpani on it during school, and my music teacher’s instruction for Jupiter was “I want you to play it like you’re determined to break the instrument.” So much fun.

      I have never heard Choctaw County Affair before, but I’m listening to it now, and I could totally see how this would work. It’s great stompin’ music!

  4. Yes! I did this before my last big job interview (the one that landed me my current position) and it really did help. I still do it as a boss, when I need to have awkward conversations with my direct reports (something which feels me with more anxiety than confronting my own manager, actually). I don’t have a go to for pump up songs- they are always rotating since I usually end up picking something from a recently watched TV/movie soundtrack scenes where people were doing badass things. It helps create a mental image of the mindset I want- someone who is focused and fierce with guns blazing. My last go to’s were pulled from the Person of Interest soundtrack (which is generally awesome), and include:

    Fortune Days by Glitch Mob
    No Wow//The Future Starts Slow by the Kills

    1. YES! This totally works! In high school, my fuck-the-administration soundtrack was Kill Bill Volume 1 for exactly that reason. (I… May have run an underground school newspaper that was blocked from our school’s VPN, because it exposed a bunch of scandals and corruption… Who can remember, it was so long ago…)

  5. I also still believe it’s 2003. Actually, that’s a lie. I’m permanently stuck in 1995 and One More Chance (Remix) is the song of the summer.

    My pump me up for confrontation song is Ambitonz Az A Ridah. Musically and lyrically brilliant while being lethally searing. I won’t deny it. I’m a straight ridah. You don’t wanna fuck wit me.

  6. I don’t have a playlist for this kind of thing but now I wish a little bit that I did and I want to say that just about anything by Reba McEntire, Martina McBride (hello Independence Day), Carrie Underwood, or anything from the Hamilton soundtrack is pretty inspiring. Also much of Moana, surprisingly. I love hearing JB randomly belt out I AM MOANA!

  7. I need this so much right now.

    My group finally told our prof about the guy who just… stopped contributing to the group project. And now our prof is making a big case of it (you need to have your group project approved before you’re allowed to sit for the exam), so I need to sit in and present our groups case to our prof and admin on Monday.

    All the while he is trying to contact me explain his case to me about how he does not understand how abandoning us mid-project might be seen as “not contributing”. Sheesh!

    We’re in such a small town right now, I will just avoid any risk of confrontation by hiding in my room all weekend.

    The worst thing is, he’s probably going to come out of this smelling of roses, because he can sweet talk his way out of anything.

  8. I never stopped to consider playing a power mix before a confrontation. I did recently put High, High Hopes by Panic at the Disco on and raped the replay button for hours when I was doing last minute prepping for a certification exam. It made me feel invincible and I think I nailed that exam. (No results for weeks). I also love “Saturday Night” by Panic at the Disco. Imagine Dragon’s “Thunder” and “Whatever it takes” will also be going into my arsenal

    Thanks for the tip.

  9. Rage Against the Machine – i mean just in GENERAL they are an excellent Damn the Man soundtrack but my 2 favorite songs for this list are Calm Like a Bomb / Bulls on Parade. (Killing in the Name – honorable mention :D)
    Raise a Little Hell – Trooper
    Woman – Kesha (feat. Dap Kings)
    Blood in the Cut – K. Flay
    One and Only – B.I.
    America’s Sweetheart – Elle King

Leave a Reply

Your email address will not be published. Required fields are marked *