Supervisors as Road Trip Companions


I was having lunch with a friend the other day, and we were discussing the best analogy for difficult supervisors. No particular reason, of course… Anyway, we finally hit on the idea of road trip companions. This struck me as a particularly apt analogy, as pretty much anyone can relate to this experience. Even if you have never been on a road trip with one of the following types of people, you almost certainly have been on a road trip with someone, and it is no great stretch of the imagination to discern what these experiences would be like:

Supervisor as Four Year Old: Gives incoherent directions when he bothers to give directions at all. Constantly pesters you with “is it done yet?” Eager for the final result until he gets it, then vaguely disappointed when he has it, but can’t say why.

Supervisor as Three Year Old: Screams a lot. Throws temper tantrums. Makes impossible demands (“I wanna go to the moon!”) Eager for the final result until she gets it, then acutely disappointed when she has it, and loudly lists off all the reasons why.

Supervisor as Passive-Aggressive Roommate: Has a clear picture of where he wants to be, but won’t give you directions of how to get there. Insists you know what you should be doing “if you would just focus”. Sighs a lot.

Supervisor as Hung-over Roommate: Has no good advice to offer. Insists that you take the wheel. Still wants to have a say in every decision. Groans a lot.

Supervisor as Backseat Driver: Insists that you take the wheel but second-guesses every decision you make. Constantly harps on your ability and distracts you at critical moments. Blames your “inattentiveness” for any problems caused by his interference.

Supervisor as Best Friend: Cool to hang out with, but makes it impossible to focus. Constantly distracting you with stories, jokes, and inappropriate comments. Makes you late for everything and miss important deadlines.

Supervisor as Crash Test Dummy: The perfect road trip companion. Stays quiet but still helps you get into the fast lane. Doesn’t mind being thrown under the bus in case of emergency.

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How To Get Ahead In Business If Your Boss Is Anything Like Me


Somehow, despite all my worst efforts, I’ve ended up supervising quite a few people over the past several years, as well as observing more than a few more come through this and other companies I’ve worked at. Between this and my own personal experiences (read: “the horrible mistakes I made and all the advice I never listened to just like you will not listen to me”) I’ve come to realize there are certain common traits that separate the people who will continue to advance and thrive from the people who will simply drift from one meaningless job to the next, only to inevitably end up complaining that the world isn’t fair. In order to empower you and prevent you, dear readers, from becoming one of those benighted souls, I offer these insights I have gleaned from my years on both sides of the managerial fence.

I Know It’s Boring, Just Do It Already. Here’s a little wake up call for you, sunshine: if your job weren’t 90% suck, I wouldn’t have to pay you to do it, you would do it for free. If it were 90% fun, YOU would be paying ME. So please, stop telling me how much the work I’ve given you sucks/is boring/is beneath you/is a waste of your time/skills/degree/god given talent/I honestly don’t give a rat’s ass. The simple fact is, the people who do what I ask them to do, do it well, and don’t complain are the ones I will come to when I need something else done, including the fun projects, and the complainers are the first ones to get cut when the budget axe comes down.

My Job Is Boring, Too. Bet you didn’t see that one coming, did ya? Yeah, cupcake, here’s the reality of the workplace: the reason I gave you all that boring stuff to do is so I could have time and mental capacity to focus on my own load of boring stuff. See, I have more experience, more institutional knowledge, more work relationships, and more understanding of how to get things done. That means that for every boring project you’re working on, I have three, only I don’t get to see them through to completion. Instead, I have to nurse them along just far enough that I can hand them off to someone else that I can only hope will bring them through to completion in a manner I find satisfactory, because if they don’t then I get yelled at for their failure. That’s called responsibility, and it’s what I really get paid for.

Take Responsibility. The people who get promoted are the people who get things done. If you can’t, come to me before the deadline and before you run out of money so we can come up with a solution. This makes you look like a problem solver. Why you didn’t get the project done on time, on budget, after the fact, is of no interest to me.

Do It Right The First Time. I shouldn’t have to say this, but somehow I do. I can’t count the number of people I have had to train in the simple fact that details matter. It’s not just about the task at hand, this goes to my overall perception of you. It’s like this: when I have a new project of critical importance, who do you think I’m going to give it to: the guy who treated his last project with a shrug and a “whatever” attitude, or the one who treated it like his job depended on it? Even if the project at hand is simple data entry, the next one might not be, and how you do on this one will shape my perception of how you will do every other task I give you.

This Isn’t Social Hour. Maybe you heard that “networking” was the way to get ahead. Maybe you never grew out of chatting with your friends in high school. Maybe you’re just naturally gregarious. Whatever it is, if every time I see you I see you talking to someone instead of getting something done, that’s the image I have of you. That’s not to say you can’t be sociable at work, but it is to say that you need to understand why you’re there, and socializing isn’t the number one reason. It’s not even in the top five.

Innovate, Don’t Inundate. Truth is I’m always open to a good idea. I welcome them. The problem is that everyone, and I mean everyone I’ve seen come into a new company throws out a new idea within a week of starting there. I’ve done it myself. I guess the urge to impress your new boss is just too strong, or maybe we all just feel like “Well, they hired me for a reason.” The problem is this is the height of hubris. This presumes you understand the company and position you are in so well within a week that your idea will have merit and strength sufficient to be worthy of consideration and implementation. Now take this hubris and multiply it by the number of ideas you’ve thrown out in the amount of time you’ve been at your current job, and divide it by the number of months you’ve been there. For most people who have been at a job for less than a year, this ratio will be roughly “holy/shit!” Even if there’s a good idea in there somewhere, I’m not going to notice it because I’m too busy ignoring everything you say. Wait for the right idea to come along, put it out there, and let others decide its relative merit.

Be Patient, And Have Realistic Expectations. There’s a great line in Fight Club that I think we can all learn from: “We’ve all been raised on television to believe that one day we’d all be millionaires, and movie gods, and rock stars, but we won’t.” I take a different lesson from this than the movie intended, but I do take a lesson away from it, and I hope you will to: you can have the corner office, you can have the six figure salary, you can have the respect of your peers and the adulation of the masses… but you won’t have it today. Tomorrow’s not looking good either. You’re gonna have to work your way up to them, slowly, bit by bit, and even once you get there, if you get there, there’s no guarantees there will be anything more beyond it – or that it’s even what you wanted in the first place. Life’s like that. So think about it, now and along the way. Be sure you know what your options are, and know what you’re giving up, because there are damn few second chances, and nobody gets a third.