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1. What is my boss worried about?
Bosses often have to project a level of confidence and authority that reflects a very optimistic and worry-free persona, and many employees are often inclined to believe that is really how their boss is. But like all of us, bosses have worries and concerns. Recognizing those worries is a crucial first step to understanding your boss's motivations and goals.
2. What is my boss's preferred management style?
Management trends come and go and many bosses at all levels are often expected to follow a particular style or technique or feel that they should. The problem is that if a particular style is not natural to him or her, it's as taxing for the boss to employ it as it is for the employee to work with it. By figuring out your boss's preferred management style, you make it easier for him or her to work with you by meeting your boss on their turf. And what's easier for them is by default easier for you.
3. What is my boss's relationship like with his or her boss?
It's a question that's rarely asked. We all have bosses, and though the chain of command only goes up a level at a time, your boss is just as accountable to a higher-level boss as you are to him or her. Studying the relationship between your boss and your boss's boss gives you insight into how they see themselves and how they relate to others whom they are accountable to, thereby providing you with a blueprint for your own relationship.
4. What behaviors does my boss reward?
This is yet another way to verify your boss's preferences and management style. Whether they are aware of it or not (and often they are not), bosses will positively reinforce and reward those behaviors they like. People assume a boss's behavior matches with what he or she most wants from others, but this is not always so. A very mild-mannered boss may reward aggressive go-getters, while brusque and curt bosses may think highly of personable and relatable individuals. Find out what your boss rewards and you'll know what he or she wants from you.
5. How does my boss represent me to others?
How your boss talks to you may not be how he or she talks about you to others, and this can be a good or bad thing depending on your boss's motivations and relationship style. We've all encountered situations where we found out that our boss was praising us to his or her other colleagues and were surprised because we weren't even sure that the boss liked us. In more unfortunate circumstances, the opposite can also be true. Whether intentional or not, how your boss interacts with you may not always be an accurate indicator of what he or she thinks of your abilities, but how your boss speaks about you to others is very much so.