Friday, April 4, 2014

How to Work for A Difficult Boss

Today’s question comes from a new reader!


Came across your blog while doing some research for a position I'm interviewing with on Monday.  I've been an EA on and off for years to pay the bills between various contracts.  My background is in management, but a girl has to pay the bills...

As I mentioned, I'm interviewing for a very high profile position next week for a Chairman of a major international company.  I seriously want this job.  I have a strong personality and don't like to take crap, but I've been warned that this guy is a serious hot head.  Just wondering if you have any advice on how to cope with a boss who is basically a rude ass, and there's nothing you can do about it.  I've experienced this before... these guys who probably have personality disorders or some undiagnosed mental condition (OCD, bi-polar, etc...) and no matter what you do, they seem to get pleasure blaming you/me... any female in the room.  I've also noted it's never a man... Whatever...  I'm certainly not a sucker for punishment, but if I could land this job and make it work without feeling like I've completely lost all self-respect, it could be my ticket.

Sort of a personal question to ask a complete stranger I suppose, but I'm sure it's more common than not.  I'm not looking for a glossy, Christian magazine answer.  I need to know how to deal with a psycho Chairman and make it work for me without it affecting me.  How does one not get unnerved when some seriously high profile jerk boss calls you an idiot for no reason.  Again, I want to learn how to cope with it for my career (this is a major position for a resume) because I know it's him and not me.


Dear M,

Glad you found my blog and thank you so much for the great question; it’s actually one I had myself many years ago!  And congrats on landing the interview!  For all my new readers, I’ll answer your question by going through your entire email.  You may already know a lot of what I am about to say so not everything I say will apply to you directly.  I just want to cover everything you wrote for any new EAs or those unfamiliar with working in corporate or the business world.

I think it’s great that you seriously want this job.  That will work only to your advantage.  If you can land this job and make it work, it will be your ticket to an amazing career for LIFE!  The most amazing assistants are the ones who can and want to work for the Harvey Weinsteins, Steve Jobs, and the executives in Devil Wears Prada, Entourage, and Swimming with Sharks.  Whether you want to call them difficult or just plain relentlessly one-of-a-kind talents, the most brilliant of leaders can be finicky at times.  Yet the fact that they can deliver at that level means they are uber successful.  If you can learn to work with them, you have skills that 99.9% of the EAs don’t have.  You will be a sought-after EA.

This question excites me because no one has ever asked this question and I’m happy for you that you are gung ho to land this job.  I am eager to answer your questions.  So I will answer, then give my personal experience.

You mention you have a strong personality and you don’t take crap.  I applaud you for those traits, as they are needed in certain situations, the difficulty is we will never know how your boss will respond.  This is depending on his “issues”  (OCD, biploar, ADHD, etc).  In general, being able to communicate well and develop a rapport with people - nice or finicky - is being able to give them what they want.  Whether they know what they want or not is a completely different story.  Working with extremely difficult people is akin to working with babies or kids.  They have no/poor communication skills, they lack intra and interpersonal awareness.  They lack compassion, empathy and sympathy, and they don’t know what they are feeling or need - much less how to express it.  This makes them unstable, unpredictable, hard to manage, and hard to understand, especially because there is not a reliable, consistent way to have them help you help them.  I’m not sure if you’ll ever fully know how to best handle his personality, but if you can manage it well ENOUGH then that's all that matters.  If you are good at reading body language, emotional cues, have a very good grasp of psychology, mental warfare, and are charming, you do have an even stronger chance of coming out unscathed.  You may also have to come to the realization that your “main” role aside from being an EA is to be his scapegoat, punching bag, and source for blame when everything under the sun bothers him or goes wrong; that you are a mere object in his life, not a person.

My advice on how to cope is below.

1) Convince HR and the hiring managers you really want this job, won’t quit soon, and accept what you are getting into.

I can hear you really want this job, but I’m sure others want this job too.  It’s “your ticket” is something that needs to be explained to HR in a way they can understand and let them know why they should choose you.  Realistically, they’ve hired this position numerous times because the turnover rate is so high.  If you are lucky, maybe HR is exaggerating how bad he is.  At worse, it is worse than even you’ve dealt with or imagined.  If you want the job, you need to speak from your heart and soul why you’re the best candidate.  You need to sell yourself in an eyes wide open, I know what I'm getting into way without being desperate or needy.

2) Have in mind exactly what you want to get out of this role.  And how will you get it?

As you interview, listen carefully if this job is the right one for you.  On paper, jobs always sound great.  Think about the ins and out of the daily grind and the overall picture of what you will get out of the working there for a couple of years.  Compare it to your life goals and how this step will help you reach the next one.  It may very well be that to say you worked for this boss for 5 years is all the accolades you will need and the great paycheck.  I do worry if you will get constant raises, bonuses, or title changes to show you’ve progressed if your boss is so terrible he will badmouth your performance or not approve salary increases.  Perhaps you want to be transferred laterally or to get promoted within the dept to being management again.  The point is, no one will care more about your career than you. Maybe co-workers will ask you to join their dept or poach you if they go to a new company.  Have goals and some strategy, but be open on how you will achieve them.

3) Have stress reduction and coping mechanisms in place.

Before you even start your job, you will need to have tricks, things to say to yourself, or methods in place to help you survive the hour or each day.  To wait until you are in the moment when things heat up, blow up, or go south is too late because not only do you have a job to do that’s hard with a great boss, it will be 10x worse to have a boss that is probably waiting for you to mess up just so he has a “good reason” to yell at you.  These methods will have to be stuff that you can do in his presence as you can’t leave and spend half the day in the bathroom or sitting in your car.  Whenever he calls you names, you may have to mentally say to yourself, “He’s just mad, it’s not about me.” And you will have to do this over and over.  Whenever he yells, you’ll have to look him in the eye, but imagine him as a little kid who never got the love and attention he deserved.  You may have to use your anger and stress to fuel being productive.  It may mean you need to exercise extra hard after work or sleep an hour early.  Whatever you choose, have various methods to use, and pick HEALTHY habits like meditation, walking, or rising to the challenge of being a good EA.  Do not pick destructive outlets like alcohol, drugs, or unhealthy food.

4) You must NEVER cry at work or show that he is “getting to you.”

Since we don’t know why your boss acts the way he does, for all we know he may actually enjoy seeing you cry or to know he got under your skin.  I say the above because while it might make him happy to see you in such a bad state, I think it’s more important for you and your co-workers to see you are strong, can handle this, and not let your co-workers get caught in the middle.  You don’t want to make them more uncomfortable having to witness/know you got yelled at and then have to try to make you feel better.  That’s a big burden for them to constantly bear as well.  You also can't badmouth him at work because he's your boss and you may have to constantly apologize to others for the way he treats them too.  You will have to be the mediator when no one wants to work or deal with him.  If he does want you to cry or get under your skin and you don’t, know this mean he could very well hire you and fire you in the same day because you “don’t click” with his style and he isn’t getting what he wants out of you, whatever “it” is.  It could be anything from always being right, to being told he is the smartest, to undoing the past where his mother abandoned him or his high school sweetheart broke his heart.  Or it could be that he is just mentally ill, has some sort of addiction, or low self esteem.  That's something you will have to navigate, but realize it's not your problem to solve, it's your problem to manage so he churns out results and you are in good standing with him even though he treats you like garbage.

5) You will really need to buckle down, do soul searching, and not let the repeated verbal and mental barrage seep into your subconcious.

Whatever you are exposed to long enough you will believe and it will become a part of you, whether or not it’s true.  That’s just how repetition and the way the human mind works.  Studies tell us that for every negative thing you hear, you need about 5 compliments to offset it.  So again, you will need to learn how to “tune him out” yet pay enough attention to details to do your job well.  You will need to ALWAYS be the bigger, forgiving person, the adult.  You will always have to take the high road.  And you will need a personal life, loved ones, hobbies, dreams, and a support system to help offset a terrible boss and the toxic work environment tenfold.  Figure out how to cultivate that.  Which leads me to my next point.

6) How will you defend your job to those who love you?

Whenever I worked a job that wasn’t exactly the right one for me, it was hard for those who loved me to see me overly tired, too stressed out, or not amazingly happy.  Those who love you want the absolute best for you and anything a smidge shy of that is not good enough.  So as you take on this job and most likely need to vent, how will you assure them you are fine as the weeks go by?  Or perhaps you will be very emotionally sound that you won't need to vent at all and can take it as a grain of salt.  You are so focused on the bigger picture, the payoff, that the stress of work is nothing compared to your resilient mind.

7)  How will you cope and lean on those who love you every time you need to talk it out and they can’t accept why you stay?

In direct connection to the above, as you take on this job you will most likely need to vent.  Know/understand for them to hear you aren’t amazingly happy, will be hard and tiresome for them.  Most often people can’t stand to hear someone fret about a broken heart after 3 months or about the same issue they’ve had with x, y, or z, for the past year or ten.  At some point, people wonder, if you know something is bad, why don’t you change it?  We know most people prefer the certainty of misery than the misery of uncertainty, but that’s easier said than done.  And studies show that other people listening to your problems experience it worse because they feel helpless, they can’t do anything, and can only watch you be miserable.  Whereas, you can actually go fix it, if you can muster up the courage and energy to change.

8) You need to figure out how to explain an exit if you get fired (not let go) to your next employer.

The best planners and most successful people figure out the end goal and work their way backwards to figure out milestones, deadlines, and the steps needed to get where they want to be.  They also do risk assessment, pros and cons, and figure out how to mitigate risk and increase success.  This is why I make the above point.  A difficult boss is very volatile.  The chances of getting fired are pretty high.  If you get let go, HR will give you a reason that you can just repeat (it wasn’t a good fit, a reduction, etc).  If you get fired for performance and that’s what HR says, you need to be able to bounce back and say what you learned, how  you fixed it, and how you will do better at the new company.  Your line of reasoning can not be he was difficult and what happened was unfair.  Blaming him, will only make you appear similar to him in anyone's eyes.  He most likely views you as the problem so it only tells everyone that you believe blaming others is okay.

9) You probably want to have in mind how long you plan on staying with him.

From what I gather you seem to want to use this as a stepping stone in your career vs staying forever.  You need to figure out how long you need to stay for it to be beneficial to your resume and the story you tell about your career.  In some cases staying a year could be enough.  If his other assistant stayed for 5 years and you only stayed for 1 that doesn’t look as good in comparison to her, unless you got a job working for the President or something outrageous like the Queen of England that anyone would take in a heartbeat.  Because it's assumed you love your job, it's great, and you'd be sad to leave because it's uncouth to admit you ONLY took a job for the paycheck.  So knowing how long you will stick it out has to be a part of your personal mantra and that you are focusing on the big picture anytime you get stressed.

 10) What is your exit strategy if you don’t plan on staying forever?

If you don’t plan on staying forever, know how you will manage your finances and your transition as you leave.  Also know your boss may be even meaner to you as he copes with losing you.  If you do need to quit and/or change your mind, have a professional way in mind that honors both of you on why you are leaving on your own accord.  This is also important if you have to train the new assistant.

11)  Have a hard line of what is or is not acceptable.

At some point, for all we know, the difficulty of your boss could escalate.  It’s generally known that humans get used to something and need more of it to get the same return.  You will need to figure out a hard line that you will not tolerate certain behavior.  As they say, if you don’t stand for something you’ll fall for anything.  What is that line for you?  And why that line vs one any average person would draw?

12)  Weigh is this worth x, y, z?

You mention this is your ticket. I don’t know if it’s the salary, benefits, career advancement, or to say you have a job.  Regardless, do some soul searching on if your self esteem, self worth, and self respect is worth whatever it is you want in exchange.  Only you will know.  What is worth suffering for?  For some it is love and enduring heartbreak or divorce, it could be exercise for a summer body, it could be giving up a dream car to put your kids through college.  What will you suffer for?

As you mull over what to do over the next couple of days, I want to share my own experiences with you.

However, I do want to state something up front.  You need to do what’s best for you.  If I knew you in real life, I would support you because I respect you as an individual.  Only you can live with the joys and consequences of your decisions because only you can live your life; no one else can do it for you.  I am here to accept you wherever you are on your life’s journey.  It’s not about whether I agree or disagree; it’s about you and helping you live your life in the moment you are in now.  I know nothing of your background, what you value, and makes you tick.  I can only tell someone, “Do you what you have to do.”

And to get into my personal experience and what works for me…  The below may not work for you at all and that’s fine.  I just want to give you a well-rounded perspective.

You mention, “I'm certainly not a sucker for punishment, but if I could land this job and make it work without feeling like I've completely lost all self-respect, it could be my ticket.”

I’ve worked for 2-3 people that were difficult.  They were very nice to me/my dept, but horrible to almost everyone else.  The worst that I witnessed was only a lot of yelling/raised voices and less on the demeaning/blame/name calling scale.  But for me to be able to hear my boss yelling from halfway across the building because their voice carries so much is rather unnerving. I've also heard the flip side, where the boss was a saint and super nice to everyone BUT the assistant.  So the assistant felt even worse because no one would or could believe the boss treated the assistant like crap.

I’ve also been called into a couple of job interviews with very difficult people.  The EA world can be very small.  I ended up hearing about the other girl who got the job because word travels.  She excitedly quit her job to work for a very powerful, but difficult boss and she was fired within two weeks.  I don’t know what happened after that.  I do know the girl who was fired found out BEFORE her company told her.  How?  My old co-worker (who was also friends with the girl) got a call to interview because they were waiting to hire a new person before firing her.

Another time, I was being interviewed by the current assistant who was leaving because she was pregnant and due in a month or two.  She was like you; she didn’t like her job, but she could do it and not let it affect her at all.  She had been there a couple of years and seemed totally blase about the horrible boss.  I don’t know what her secret was, but it seemed to work for her.

Even if she told me the secret, I wouldn’t actively use it in my life.  I wouldn’t use it to my advantage.  Why?  Because I’ve read enough books looking for the same answer and this is what I learned.  Do not work for difficult people.  Not only is it bad for you personally, but it also means you condone the idea that treating people badly is a good idea.  It really just boils down to an ethical issue; a human rights issue, and a philosophy of life.  I want to be a beacon of positivity, hope, and change.  It’s why I write this blog for free with no strings attached; it’s how I give back.

I also know myself well.  I am great at working under pressure, with deadlines, for DEMANDING, not difficult people.  I draw the line at yelling, name calling, verbal abuse, mental abuse, and any sort of “asshole” behavior.  I believe life is HARD.  Life is ALREADY difficult enough - people get sick, people/pets die, people get their hearts broken, and to weather those storms that you can’t control are hard enough while battling a bad boss, a shitty job, a stressful, high pressure role, and that much emotional/mental stress 40+ hours a week.  What works for me is to cultivate a life and environment with an abundance of peace, relaxation, joy, and fun.  I do invite learning, challenges, growing, and stress, but I can only function at my best in life, at home, and at work when I am surrounded by professional/supportive people who want the best for me too and will be positive mentors.  I work 40+ hours a week, some weeks that alone is tiring.  There are periods during the year where I pull 60+ hour weeks; those are grueling, but I do it HAPPILY because I love my job, my team, my boss.  I am EXTREMELY lucky.  I also know, in the end, people don’t die wishing they worked more.  Life is more important than that.  There is other work to be found.  There is another way to pay bills.  You only need so much money to be happy.  Know what you want out of your ENTIRE life and start there.

As you figure out how to make this role work for you, here are 3 things to think about.

1) Both of the jobs I was interviewing for, had they had told me over the phone up front how difficult the bosses were, I would have declined the interview right then and there on the spot.  What happened was as soon as I showed up on the interview, that was something they told me within 10 min or something I figured out half way through by all the clues they were dropping. And I had to say outright I was not interested in the role because it wasn't the right role for me.  It was a little awkward as one interviewer still continued to interview me instead of cutting it short.  Not sure why.  The 2nd one, it took me a while to figure out how to bow out gracefully because I was so caught off guard on how I was fed bit and pieces of how horrible the boss was as if that'd lessen the blow.  Because as you say yes once, and the over the course of communicating, the more committed you become, the harder it is to say no all of a sudden.  And with anything worth doing, you have to make a commitment to the commitment.  (Believe it or not, this is a brainwashing tactic used against prisoners of war.  Make them admit/agree/and write one "harmless" statement because once they admit to that and agree, they lose face if they don't agree to the next escalated statement.  Agreeing to one "harmless" statement makes everything else snowball because you gave in at the beginning because that seemed easier.)  I read a quote that said, “If you’re interested, you’ll do what’s convenient.  If you’re committed, you’ll do what it takes.”  So think about what you are committed to.

2) All the books I’ve read on how to work with difficult people only mention to leave.  The coping strategies aren’t for staying long term.  It’s for how to get out; much like how to plan an exit strategy if you are dating an abuser - whether verbal, mental, or physical.  Because working for a difficult boss is in essence the same type of relationship, it just so happens to be at work.  The bottom line is, if you are not thriving, you’re in a losing battle.  At the very bottom are the 3 books I read.  May they provide some further insight as well.

3) I know you’ll make the right choice that’s best for YOU.  I don’t know what that is, only you do.  Because it’s also true that horrible bosses still need assistants.  And that people do sometimes change.  Here’s another quote that can be just as relevant by Emm Cole, “When you do find your enemy, remember he will expect and welcome your hate.  So surprise him, and let him fear your love.”  It all comes down to where do you draw the line and what do you want for yourself.  Either way, I’m excited for your life journey.  I chose to answer your question because I want to help you be and do whatever it is your heart desires.  I wish you love, luck, and the best on all your endeavors. I would love to hear what happened.  I’m sure my readers would too and I’m sure you’d love to hear them weigh in with their personal experiences and suggestions.  Feel free to keep me/us posted and to ask more questions if I haven’t answered you completely.  I’ll end with this quote.  

“No one can make you feel inferior without your consent.”   -Eleanor Roosevelt

Suggested readings:

The No Asshole Rule: Building a Civilized Workplace and Surviving One That Isn't by Robert I. Sutton

Working With You is Killing Me: Freeing Yourself from Emotional Traps at Work by Katherine Crowley

You Want Me to Work with Who?: Eleven Keys to a Stress-Free, Satisfying, and Successful Work Life . . .  No Matter Who You Work With by Julie Jansen


***New “rule” - when you ask me a question for anonymous advice and I answer it, could you write an anonymous comment so I know you read the post?  You can just write “Thx!” or something!  :)

As always, I usually tweet any new posts I have. And anyone can email me questions and I respond only via this blog, not to your personal address.

I also write over at under Hollywood Executive Assistant.


  1. I just read your thorough and authentic response to my question and I'm still processing all of it. I can’t express how wonderful and strange it is to have an actual conversation with someone who is intelligent and frank on this subject. I don’t have any friends who are EA’s, so I’ve never been able to talk about this with someone who is smart and who operates at a high emotional level. I would like to engage and share a bit more as this type of introspection will definitely be a helpful exercise. Thank you thus far for sharing your thoughts. It’s the first time I’ve read something on this subject that truly provided valuable insights. More to come… M

    1. The Muser at Musings of A High Level Exec AsstApril 5, 2014 at 1:43 PM

      Dear M - I am glad to know you are taking the time to process everything I wrote. I am happy to know you feel it was thorough and authentic. I really appreciate you expressing, "how wonderful and strange it is to have an actual conversation with someone who is intelligent and frank on this subject," and, "is smart and operates at a high emotional level." I don't have any EA friends as well, but I do have a wonderful support system. So, I do understand the value of being validated by someone in the exact same situation which is why I'm so glad to have this blog for other EAs. I hope you find the answer you are seeking and your comment truly means a lot to me. I really like helping people and hearing from readers always makes my day. Have a great weekend and week.

  2. Hi Muser
    I enjoy reading your musings and totally agree with M's views of you.
    While I may not face the situations in the articles you shared, I find them very informative and file them away as a useful guide to refer to.
    Thank you very much for sharing your informative and wise thoughts with us and I'd like to let you know that though I may not know you personally, you're my inspiration and someone whom I admire greatly :)

    1. The Muser at Musings of a High Level Exec Asst.April 22, 2014 at 1:40 PM

      Dear Anonymous - It's so nice to hear from readers! I am so glad my blog has been helpful and enlightening to you! It is such a joy for me to write and hopefully help others and I thank YOU for the comment and being a reader! I am so very flattered when you wrote: I'd like to let you know that though I may not know you personally, you're my inspiration and someone whom I admire greatly :) I have been reading a lot of great books lately always trying to learn and expand my horizons. I hope you have a great weekend!

  3. Hello,

    This post is amazing! I was glued to the screen reading. You write so clearly and full of wisdom! Thank you for sharing your experience!

    1. The Muser at Musings of a High Level Exec Asst.July 3, 2014 at 2:44 PM

      Dear Anon,
      Wow thank you for the compliment! I am so happy you were so captivated and were glued to the screen! I am so glad all of my writing was clear to you and insightful. I spend HOURS writing and then later I still find typos sometimes that I haven't had the chance to fix. Aaaaggh! But that's why I write for free and for the love of it when I have the time! Hope you have a great 4th of July!

  4. Wow!! You are amazing and on point with your advice!

    1. The Muser at Musings of a High Level Exec Asst.July 8, 2014 at 5:09 PM

      Anon - Thank you for the comment and being a reader. It's nice to hear from other EAs.

  5. Well, I am speachless by your approach to the topic, you really not left anything out of the point. I am EA myself and have worked for "not so easily manageable" superiors, actually twice in my 9 yrs carrear. Just for statistic's reasons I will say that the second experience went super gut and turned out to my benefit, since I was well perceived by him and HR as the assistant that managed to handle his demanding requests with success, got promoted, salary raise etc. while the first experience did not get that well, I, sooner than a week knew that I had to find another position and leave nicely and professionally from the company which I finally did within 3 months. This makes a 50-50 in my case as one case went wrong one went very well indeed. In my case though, crucial details is, that I was clueless of the temperament of the above mentioned superiors and I had to find out myself. Definitely I would have skipped the experience if I knew up front the case. Lots of love and all the best to you, keep up the superb work (apologies for my English, is not my native language xoxo)

    1. The Muser at Musings of a High Level Executive AssistantNovember 13, 2014 at 1:17 PM

      Dear Ms. Maus - Thank you so much for your comment. I am so flattered that you felt my answer was very thorough and in-depth. I am sure other readers will enjoy hearing your 2 experiences and how it is very much a 50/50 chance on what will happen. Thank you for sharing. I hope many more great experiences are in your career path and you read older posts or my other blog at under Hollywood Executive Assistant. It is so nice to hear from readers from all over the world so thank you for being a reader!

  6. Wow... what a great post. I am in the process of obtaining an EA for myself and can admittedly be difficult to deal with (ocd male). Your powerful words have helped me see what arrogance has hidden from me. Thank you.

    1. The Muser at Musings of a High Level Exec AsstJanuary 28, 2016 at 5:41 PM

      Dear Anon - For some reason, I just saw this reply now. Thank you so much for the kind words. I'm glad you liked it!

  7. Wow - I admit to only having time to scan right now - but this is my life - although the my boss is a woman - been at it for several years and I am struggling big time with whether to hang in there for the paycheck... Am completely self-supporting. I will come back in the next day or two and read through all of this carefully and comment in more detail ... For now time for bed - Thank you - Anon-RGO

  8. Hi, love your blog and this post made me think about my past experience with an "high demanding" exec. And yes, I totally agree with you, the best thing you can do is to change of job! Although at the end of the 2 years working for the Minotaur (that's how me and many of my co-workers called him) I gained his esteem, got bonuses and pay raises, I am so happy I managed to leave that position and I would never work for someone like this again. NEVER. There's not enough money in the world that could pay back for the stress I had to go through these years.
    Thank you.

    1. The Muser at Musings of a High Level Exec AsstApril 25, 2016 at 12:39 PM

      Briseide - Thank you so much for your comment and being a reader. I am so glad other EAs can read the comments and hear from people like you and what you did. Congrats on taming the Minotaur and getting all the bonuses and pay raises! GOOD JOB! I am also glad to know you left and also knew there are more important things than money. I hope you are happy wherever you are now! Thank you so much much!