Defense Against the Jerk Arts: Dealing with a difficult boss

Updated: Oct 13, 2019

Executives are a special breed.

They’re often under a lot of pressure, frequently surrounded by yes men, and though they are probably quite brilliant at what they do, they may not be fantastic at things like respectful communication. Translation: sometimes they can be total jerks. And as a support professional, this can be a real challenge for you not just as their direct report but as their representative to the outside world.


In this post, you will learn:

  • Tantrum prevention tips

  • How to protect yourself from an exec on a rampage

  • How to offer support without enabling bad behavior

An ounce of prevention…



Let’s be real: no matter what you do, your boss is likely to have the occasional meltdown. But if you’re supporting a frequent flier on Apoplectic Airways, there are precautions you can take to minimize the frequency and intensity of the blow-ups.


Understand their motivations


Ask yourself why your boss does what she does.

  • What is she trying to accomplish?

  • What is she trying to prevent?

  • How does she measure success?

  • What looks like failure to her?

If you can act and speak in a way that lets her know you understand and share her values and concerns, that’ll help quell the anxiety fueling the upset.


Identify common triggers


Make note of what tends to set your boss off, and try to head those things off at the pass. If he gets anxious when he travels, make sure you make a killer travel folder for him and check in with him regularly. If he gets cranky when he’s low on caffeine, bring a fresh cup of coffee to your 1:1.


Anticipate, be proactive. It's what support professionals do.


Do your job



Best way to starve out a bossy boss’s supply of ammo is to do your job and do it well. Show up early. Be prepared. Do what needs to be done before you’re asked. Show your work. Add value. If you can’t do that, it’s probably time to…


Support a better boss


I would be remiss if I did not mention that the best means of preventing a boss from being a bully is not to work for a bullish boss. There are plenty of executive fish in the businessea.


What you put up with, you end up with. So stop putting up with it!


“I’m not going to let you hurt me”



Recently, I took a parenting class: positive discipline for preschoolers. And I was floored by how much of what I was learning applied to my work life as well.

I like to joke that Executive Assistance is “babysitting… on the highest possible level.” But it turns out that’s not such an exaggeration. Some things are universal, regardless of age.

One of the most useful things I learned in that class was to stop telling my kids–or anyone, really–what to do. Because, guess what? That never goes over well, with anyone, at any age. We all want to feel autonomous and like we are in control.


Instead, when someone is behaving badly, tell them what you will do if they continue.

If a child is throwing a tantrum, for example, we were advised to say, “I’m not going to let you hurt me, and I’m not going to let you hurt yourself, so if you can’t calm your body down by the count of 10, I will take you to your room.”


Likewise, if your boss is throwing a fit, you are well within your rights to say:

“I don’t function well when someone is yelling at me. If you can’t lower your voice I’ll have to come back later.”

If a child refuses to put on her shoes, we were advised to say, “I see you haven’t put your shoes on yet. I’m going to come back in two minutes. If you don’t have your shoes on by then, I’ll put them in a bag to bring with us, and you can walk to the car barefoot.”


Likewise, if your boss is not respecting your time, try saying, “You’ve come late to our 1:1 twice in a row and haven’t looked at the agenda I sent. If you’re not ready to go at 3:00 today, I’m going to Starbucks and buying myself a latte on the company card. You can meet me there.”


But, and here’s the most important thing: you must follow through. If you say you’re going to do something, you had better do it. Or just like a toddler who figures out that “get in the car or I’m leaving without you” is an empty threat, your exec will quickly learn to ignore you.


“What I heard was…”


Another useful trick is to go into what I call “SAFER” mode.


Say what you’re feeling

Alert those around you

Frame your present circumstances

Ears open

Repeat back what you hear


First, let your boss know you’re feeling triggered by his behavior: “It’s hard to stay engaged and rational when you threaten to fire me. I’m feeling really unsafe and upset.”


Then, remind yourself that although the situation may feel life-threatening, it probably isn’t. It probably isn’t even career-threatening. It’s just an emotional storm that will soon blow over.


Finally, listen to the actual words coming out of your exec’s mouth, and repeat back what you’ve heard. “What I’m hearing you say is that you need me to straighten this out by end of day today, or I needn’t bother to come in tomorrow. Did I get that right?”


That gives your exec the chance to slow down and listen to what he’s actually saying, an opportunity to amend or clarify it, and lets him know that he has been heard and doesn’t need to continue.


Support, not suffering


Support is a tricky business. Sometimes it looks like doing things for your exec or helping them delegate so they can focus on other things, and sometimes it looks like enforcing that they do things for themselves. Sometimes it means learning how to work with/around someone’s quirks and foibles, and sometimes it means helping them shore up areas of weakness and improve. Knowing the difference is the deep work of assistance.


But one thing is sure: support should not be martyrdom. If you’re letting someone mistreat you then you aren’t supporting, you’re enabling.


Real support occasionally requires some frank and candid feedback. And, if done correctly, any exec worth their salt will recognize that this is a valuable service you are uniquely positioned to provide.


So, here’s how to give constructive criticism without triggering defensiveness or backlash:


When and where matters


Remember that time in the 4th grade when your teacher called on you and you didn’t know the answer, and she scolded you in front of the whole class for not having done the reading?


Did that inspire you to do your homework, or just to make angry cartoons about the various ways your teacher could die in a fire?



It’s OK, you don’t have to answer.


Nobody appreciates public humiliation. It feels threatening, like something to fight against rather than something helpful to take in. I’m willing to bet your boss is no different.


In public, keep a united front. Defend your exec, foibles and all. No gossiping or complaining, and absolutely no calling out in front of others. After all, their brand is your brand, too.

It is in your best interest to make your boss look good even when he’s behaving badly.


In private, though, bring the real talk.


Build a better compliment sandwich



The idea behind a compliment sandwich is that you start with a compliment, then give constructive criticism, then close with another compliment, thus “sandwiching” the more difficult to swallow portion in a delicious praise-dipped coating, kind of like wrapping a dog’s pill in a hunk of liverwurst.


The problem with this, of course, is that you’re fooling exactly no one. People always know when a compliment is insincere, so instead of taking out the sting, it just becomes a harbinger for the other shoe that’s about to drop.

HOWEVER, there is a technique I discovered about 5 years ago that is so incredibly effective, I like to refer to as my magic trick. I figured out that if I started any potentially difficult conversation by expressing GENUINE ADMIRATION for the person I was talking to, it immediately disarmed their defensiveness reflex and put them in a more confident frame of mind, making them more open to hearing about ways they could improve and become even MORE admirable.


The trick here, and I cannot stress this enough, is that you have to find SOMETHING, ANYTHING that you actually admire about this person or the way they are behaving currently. Even if it’s just, “I really admire how passionate you are about this,” or “I have always been impressed by your tenacity. You don’t back down easily, and I could learn a lot from you on that front.”


Next, empathize. There’s a reason for the behavior. Let them know you understand it from their point of view.


Then, share what you’ve observed. DON’T psychoanalyze or evaluate the behavior, simply say what you’ve seen and experienced, and the effect you’ve noticed it having on yourself and others. Bonus points if you can point out negative consequences that affect THEM, not just you.


Finally, suggest a specific course of action and offer your help and support in carrying it out. Don’t just drop a bomb and walk away, let them know you’re on their side and willing to put in the work to help them improve.


These are your GEMS:

  • Give genuine admiration

  • Empathize

  • Make observations

  • Suggest specific action & offer support

An example:


“Great job in the team meeting today. That discussion you led about our company values was super helpful and inspiring. Listen, I know you’ve been really stressed about the sales numbers, and I get why you made those disparaging remarks to the sales team today. But calling them out in front of the whole team affected everyone's morale. People are asking me if I think they should be updating their resumes. I recommend you make a point of finding something to celebrate, and meanwhile I’ll keep doing damage control and reassuring folks that nobody is losing their job.”


Of course, this is a lot easier when the behavior you’re observing is not directed at you. Same principals apply, though. Try to state it as an observation, not an accusation, and offer your help at the end. So, instead of, “It’s not OK for you to snap at me in front of other people,” try:

“You know I love your directness, it’s one of the things I value most about your leadership style. And it must be really frustrating to have to ask me for something more than once, especially when you’re in a hurry. But when you snap at me like that in front of other people, it erodes their confidence in our partnership and undermines our collective authority. If you can make an extra effort to just remind me calmly if I forget something, I will make an extra effort not to make you repeat yourself. Deal?”

And guess what? This works with other people, too. Not just your boss.


It even works on toddlers.

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