How to manage your horrible, no good, very bad boss...

I literally was crying on the way to work one day, thinking that today was the day I was quitting!! These were tears of frustration, anger, and just hopelessness. Looking for a distraction on my drive to work, I pushed play on my new audible and the voice literally opened with something like “Do not quit your job, I know it sucks for XYZ reason, but trust me DO NOT QUIT your job!” That voice was Jon Acuff from his book: “Start: Punch fear in the face, Escape average, Do work that matters” and he apparently was directly talking to me.

I took the leap to be my own boss a couple of years ago and so far I have NO regrets. One of the reasons that compelled me to take the jump and start my own business (with my awesome partner Jessica) was working with a couple of crazy bosses. I used to be that person that bitched your ear off about my psycho boss and all of my depressing job experiences. Looking back I can honestly say I survived without burning any bridges and surprisingly made a graceful exit. I wanted to put together a post on how to deal with a bad boss, making the situation work for you, until it was time to say peace out, to a better place. 

What makes a bad boss?
(turning you into a very disgruntled, whining, angry employee)

Before we start listing all the ways a person can be a bad boss (which can get extensive) lets start with how they can fly under the radar…for YEARS. The most evil type of bosses are the ones that don’t appear to be bad and twist the knife in your back oh so slowly where you think its your fault. I am talking about the ones that look really great on paper with amazing credentials, degrees/awards, win over the board every time, have deep pockets, and even bigger networks. Resulting in a person you think should be respected, obeyed, and worst of all never questioned.

Some examples of Bad Bossy-ness:

Which is really just listing the characteristics of a psychopath…yep, I just went there. If anyone has dealt with a really bad boss, at the end of the day you go “why is he/she so psycho?!” and this list confirms it:  

 The above list is from Robert D. Hare's Psychopathy Checklist-Revised (PCL-R) and you can read more about it here. Ok so we have defined the problem, and because I really don’t want to point fingers and give you my own crazy first hand experiences, (at least not today;) I want to move on to my suggestions for dealing with this type of boss.

How to deal with the “crazy” boss?

Before I say anything please note: if your boss is doing even half of the list above- report it and get out! Physical, mental, sexual abuse is real and should never be tolerated. I have seen employees take all kinds of abuse year after year because they “need their job” because of XYZ reasons. And the bottom line is: NO job is worth that misery and abuse, there is light at the end of the tunnel once you walk away - trust me!

BUT when the boss is a ‘mild case’ of crazy here are my suggestions:


You know how bees and dogs can smell fear…so can monster CEO’s so never show them you are afraid. I know thats easier said than done. This is what I would keep in my head when talking to a boss that made everyone else quake in their boots: their life sucks - literally- no one likes them, they have no social circles, divorced or about to be, no hobbies, bad health, bad breath, workaholics etc. So when looking at the big bad wolf as a weak creature you are remembering they are human. Flesh and blood and remember they take really large shits that stink too.


As a creative we tend to have to ‘fight’ for what we believe are good design choices. The idea that some boss’s daughter gets to pick the theme for the next ad campaign is just ludicrous and needs to be voiced. SO we as creatives have to speak up with precision, listing the reasons why, based upon research, strategy, etc. We have to challenge the executives all the time. So you get less and less scared to talk with them. They get used to you and you get used to dealing with them. So then the rest of the company starts looking to you to: “go talk to them for me”, “they like you and will listen”, “you ask, you are brave”. At more than one job I was nominated to go “talk” to the boss: Asking for the next social event, changing HR rules to suggesting meetings on Friday evenings are not such a great idea. This is because I developed a direct relationship with said boss. So be the one that delivers the next campaign, speak up and be the one that explains the last client meeting, ask for direct marching orders to share with the team. Engage more without fear and they will listen.


So you now have a relationship with said boss, they know who you are and are willing to listen, keep this relationship positive by always being direct and HONEST. You are not afraid to look them in their eyes and give them direct and concise information- now pair it with your very honest opinion. Hear me out…just for a sec, put yourself in their shoes (I know, its painful) but trust me everyone is out to get them and they really don’t  know who they can trust. A boss regularly juggles: clients, new product development, sales teams, hiring new people, managing the board of directors, meetings with CFOs, not to mention trying to tell family they won’t be home for dinner again, and some employee is whining that they don’t get any damn attention?! They have no time for bullshit. Period.

They trust you will deliver quality work, direct answers, and now tell them your honest opinion. For example here are some opinions I voiced to my boss from either me offering or he/she asking me directly: What is the moral of the team?, How is X campaign going- in your opinion what do we need to do to kick it up a notch?, X employee's significant other is very sick and the company should send flowers, X person went above and beyond on the project and your appreciation would mean the world to them, etc. The truth is they are thinking about so many other “major” items on their to do lists- being extra nice to a sad employee or knowing the company moral level is not in their radar or even their wheel house. This is usually part of what a good executive assistant does- but I have seen even the best EA's too scared and not respected enough from X boss to make an impact. The boss looks to you because you do good work, give direct answers and is used to working with you. So they will honor and look for your opinions as well.

Bottom line #1: If you know you are doing quality work by continuously bringing your best efforts you should have no problem sharing your opinions because you have continuously proven yourself as an asset to your boss. In their own way they will respect you for it.


Another thing that sometimes happens with bad bosses is you never get to “finish” a project. What I mean by “finishing” is when there is a project, brief, new client, or product launch etc. that is your responsibility, there are so many factors that stop you from completing the job based upon how they run things. Not finishing a project means no satisfaction and job validation, making you feel insecure, not allowing you to be: confident, direct, honest, performing at your maximum level, etc. So another strategy in dealing with a badly run company is finish the project that you were given to the best of your capabilities. Even if that means doing it off the clock and on your own. This is for your health, feeling a sense of accomplishment and for your future job. You can use this as proof that you went the extra mile even with so many road blocks. You did what you were hired to do. All of us need to feel valued and the self satisfaction of reaching your project goals.

The main reason for this bit of advice is to plan your exit strategy and with that you need examples of what you did, how you preformed, and the results you brought to the company. As an employee you could get belittled, rudely misstated, talked down to, etc. but you know you did the right thing and can voice it when your interview comes up for your next job.

Bottom line #2: A job is a job (until itsTHE job) and what I used to tell disgruntled workers (after I stopped being one) is you either learn how to deal with it finding the good in the situation or you figure out how to leave.

Lastly I really want to say if your boss is crazy and you know you are a hard worker and do everything you can to engage for the benefit of the company or project at hand, then move on! Get over that they are crazy and treat you bad- crazy people happen and we all gain great stories from their situations- I have a TON! Life is too short to be in a demeaning and unrewarding job experience. 

BE you and BE happy! :)

Virginia Upshaw
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