factors that made one enjoyable, satisfying, or rewarding and another boring, frustrating, or just plain hell. Be as specific as possible. Consider everything from the company’s location, the size of its (or your) offices, perks (or lack thereof), your subordinates and supervisors, responsibilities (or lack thereof), promotional opportunities, and hours.
The more comprehensive you make this analysis, the more easily you will begin to identify behavioral patterns. This exercise may help you hone in on a particular requirement (a corner office), something to avoid at all costs (a boss who’s passive-aggressive), or even some aspect of your own personality that you need to work on (lamenting a lack of promotional opportunities when you’ve never stayed at any job longer than six months!).
What can I learn from past bosses?
How well do I interact with authority figures—bosses, teachers, parents?
Even if every other aspect of a job is wonderful, you could be dying to move on just because you hate your boss. Hey, it happens. So before you extract yourself from the frying pan and deposit yourself directly into the fire, you might want to do the following exercise as well: Make a list of every boss you’ve ever had, using the broadest possible definition of “boss.” Divide them into three lists: those with whom you never had a problem, those with whom you had some problems, and those with whom you always seemed to have problems.
After you’ve developed these three lists, try to identify the common factors that would explain the problems you had with the third group. Were they all old, married, white men who smoked cigars? Were they all fast-charging sales types? Were they all bosses for the same kinds of companies (large, small, whatever)?
You get the idea. The more you know about the kinds of bosses under whom you’ve thrived and those beneath whom you’ve withered, the better chance you have of finding the right fit the next time around.
I’ll use myself (again) as an example: One of my early jobs in magazine publishing was as an advertising sales representative for a trade magazine. I was ambitious, passionate, and a very good salesperson. After teaching me about the basics of ad sales, my first boss pretty much kept out of the way and let me run. Boy, did I run! I set a single-year sales record that, I’ve been told, still stands.
Now, I didn’t exactly do everything by the book. In fact, I threw the book away. I ignored all requests to do memos or reports or anything that would have taken time away from making sales (i.e., making more money). I did not communicate; I did not summarize; I did not report. I just sold. After a short time, my boss simply stopped asking for that stuff and decided to revel in the big jump his own income was taking due to my unbridled efforts.
I did so well I got promoted to a bigger magazine, becoming the youngest sales manager in that company’s history. My old boss went to my new boss and sang my praises. But he also told her, in virtually these terms, to just “let him the ___ alone. He’s a maverick and won’t follow any of your rules. He will make you a fortune, but he doesn’t need to learn anything from you. Just let him sell and motivate his salespeople to sell.”
Well, my new boss wasn’t nearly as flexible as my old boss had been (nor, obviously, as bright). Instead of adopting the recommended hands-off attitude, she wasted days of my time in a series of meetings explaining “how we do things at this magazine.” It was a disaster from the get-go, and it wasn’t long before it was made pretty clear (by the VP of Sales) that one of us was not going to be left standing.
A tremendous opportunity to move up to publisher of a major consumer travel publication materialized, as if on command. It represented a huge jump in responsibility and an equally huge jump in money. The only downside was that if I wanted the job, I would have to move to the Midwest, though my