Addressing Authority The Right Way

In late July I lost my job working at a restaurant because I told my boss that he wasn’t doing enough to keep the kitchen clean – other than posting “how to” posters on the walls for everyone else.

The fact of the matter is I was exhausted from working 60 hours every week, 14 of which were unpaid, and he asked me why I was looking so rough. I told him it sucked coming into a restaurant with a pile of dishes up to my waist every evening after sitting in an office writing all day. I told him things don’t get cleaned properly and I told him he shouldn’t leave tools that have touched raw meat in the sink. This is pretty standard stuff working in a restaurant but, he’s bad at taking criticism so he threw a tantrum and fired me for insubordination.

Of course, I’m smart enough to know that having respectful criticisms of your boss isn’t legally insubordination so, I fought them on it and received a nice chunk of severance in exchange for them continuing to run their store like a pile of garbage.

In that moment I found that my manager was not a pleasant person and more so he was an irresponsible person. But in hindsight, I probably could have approached the situation better.

There were three fatal mistakes I made when began negotiating with authority: I didn’t know what I wanted or needed from the interaction; I didn’t plan ahead of time to refine my words; I didn’t know my manager was such a sensitive baby boy – sorry, I had to.

Here are some tips that might serve as a good guideline for the next time you negotiate with your boss.


Visualize the experience and know what you want from it

You should have a rough script. Whether it’s a better wage or better treatment that you want, you need to know how you’re going to ask and where to go from there if the answer is yes, no, or maybe.

When I told my boss about the cleanliness of the store I was just ranting and listing off things I, and many of my co-workers, noticed for a while. I was basically just venting with no real end goal in mind. If I had gone into thinking about what I wanted – more initiative to clean, fewer managers standing around doing nothing, and more people washing their dishes after prep – I might have a chance to keep the situation calm and maybe I would have kept my job with improved circumstances.

You can’t always get what you want, so keep in mind what you need

This is where haggling skills come in handy. You may need a 10% raise to be able to continue surviving in your job but what you really want is that 15% raise because why the heck not? It’s always good to set a significantly larger goal than what you think is possible. This way you have somewhere to go if your boss doesn’t want to fly with the first offer you make. In that case, you still get what you need to survive, and technically what you want, while making your boss feel like they’ve won. Which gives you more leverage a year later when you think you deserve another raise.

Yes, I wanted my boss to pick a ton of slack when it came to cleanliness but I would have settled for him just doing his dishes instead of leaving them in the sink all the time. Another reason planning ahead is always beneficial.

Know the kind of person you’re approaching

I thought I knew my boss well enough to know he would be mature and calm discussing business operations with me – I was wrong. It can be hard to read people properly, especially in a busy work environment where most of your interactions boil down to talking about work and minor things in our lives. This is by far the most difficult thing to do but, I think after a year of working with someone you should have a good grasp of the attitude and surface personality of most people you work with.

If you don’t, take some time to do your research – a week or two – so you have time to think about everything else you need to be prepared as well.

The first time is always going to be hard but it’s guaranteed to get easier with every time you need to go through the process. You will make mistakes and you will learn from them but, hopefully, this gives you a head start.