Five Tough Bosses…. and How to Deal


Five tough bosses

Humans are flawed and bosses are humans and therefore, plenty of bosses are flawed. The bad news, of course, is that there is little to nothing you can do to rid yourself of a bad boss in the short term except look for a new job. You can also sometimes — sometimes — outmaneuver and/or outlast a bad boss.

But really, your energy is better spent learning to deal with the difficult people. While there are some people who operate in genuinely bad faith, most bosses are doing their best, just like you are. But the first step to getting along is figuring out what sort of boss you’re dealing with.

Enigmatic Boss
Enigmatic bosses are like the wise old wizard in an epic saga. They show up to offer some confusing tidbits of maybe-wisdom and then send you on a quest that you don’t quite understand. This is usually, but not always, delivered with a knowing gleam in their eye.

Sample Enigmatic Boss dialogue:
Enigmatic Boss: ‘Laura, I’d like you to put together a PowerPoint on marketing.’
Laura: ‘What aspect of marketing?’
Enigmatic Boss: ‘Surprise me.’

On the upside, this person has enough faith in you that they think you can do whatever it is they’re asking, even if you’re not quite sure what they’re asking for. On the downside, the first time you deliver something other than what they wanted, they can also turn out to have shades of Angry Boss (see below) in them.

How to deal: Time is your greatest asset with this kind of boss; you’ll soon learn to read between the very, very sparse lines and figure out what they actually want. In the meantime, figure out someone they’re close with in the office who is more talkative and pick their brain about what’s expected.

Indecisive Boss Who Also Wants to Micromanage

This is even worse than Enigmatic Boss. Unlike Enigmatic Boss, who at least knows what she wants but is willing to allow you some freedom, Indecisive Boss That Also Wants To Micromanage isn’t sure what they want, but they know when you’ve done it wrong.

Sample I.B.W.A.W.T.M. dialogue
Laura: Hey, so how long did you want that report to be?
IBWAWTM: Oh ‘¦ well. Um. I guess ‘¦ I don’t know. Couple pages, maybe? Maybe longer? It depends.

(Laura takes this information and writes a four-page report).

IBWAWTM: Oh, this is WAY too short. Way too short. And why didn’t you include something about our new widgets?

How to deal: Ask this person a series of leading questions, because otherwise you will spend all your time doing not quite what they wanted. Get every detail that you can nailed down, but also be developing your own internal compass on how to do your job well, since this boss’ feedback will be, at best, only mildly useful.

Lecherous Boss
Lecherous Boss just loves that sweater on you. Lecherous Boss wants to lean in real close while you’re trying to type on your computer. Lecherous Boss was wondering if you’d like to knock off early and have a drink? Lecherous Boss goes in for the hug even when there is no indication that the other party wants a hug.

How to deal: Document, document, document. Every time they make you feel uncomfortable in a way that would be easily understood by an outsider, write it down — time, date, location, what happened and who was there. Talk quietly to others in the office who have maybe had similar experiences. Then take it to HR.

In a perfect world, this would always be enough. But unfortunately, some organizations aren’t large enough to have HR and others won’t take the side of an underling against a boss. If this is the case, polish your resume and start looking.

By-the-Books Boss

By-the-Books Boss LOVES the company you work for. They have swallowed the Kool Aid and purchased the logo-embroidered fleece vest. Any decision, no matter how poor, that the organization makes is to be accepted without question. After all, if the company’s doing it, it must be right.

Because of this boundless faith in company policies and regulations, this person is likely to be a huge stickler for the rules. They are the ones who want every form filled out in triplicate and who will have minor freak-outs about any un-crossed T’s or un-dotted I’s.

How to deal: First, don’t engage this person in critical discussions about the company because they really aren’t going to hear it. Instead, focus on understanding why they love the organization so. Really, it’s great to work with someone who is super, super into their job, even if it can be a little annoying in the day-to-day. Working for a highly detail-oriented boss is a great way to develop your own detail orientation, which is a useful skill no matter where you go or what you do.

Anger Boss
Anger bosses rule through fear. They rarely communicate using their inside voices, choosing instead to go with some nice, old-fashioned yelling. They feel just fine about dressing down someone in public.

This is probably the toughest boss to deal with, because their unexpected rage storms can happen any time, which creates this constant state of low-level anxiety in the workplace. They also create a work environment where it’s acceptable for people to bully one another, which can make things very toxic indeed.

How to deal: First off, when you’re getting yelled at, imagine yourself as a smooth river rock; the swirling currents of rage passing over you without affecting you. Don’t ignore them entirely; listen for the relevant information they are giving you, even though it may only make of 10 percent of what they’re throwing at you. Realize that it’s not personal, and that this is a reflection of this person’s inability to communicate effectively. Then go find you a new job.


Kelly Williams Brown is a features reporter, humor columnist, amateur doodler and the author of ‘Adulting: How to Become a Grown-Up in 387 Easy(ish) Steps.’ Enjoy her opinions and observations on her blog.


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