How to Connect With Your Boss

Photo:  Jackson Carson

Want a quick way to connect with your boss? Show him or her that you understand what’s important to them. Whether it’s landing a certain kind of client, producing a certain deliverable, or hitting certain numbers, show that what’s important to him or her is what drives you.

When I first started bartending at a restaurant in Wisconsin, my boss was the owner’s daughter. She was a young Greek lady who didn’t take any shit and knew the business well.

I was the youngest bartender (I still don’t know why she hired me in the first place), and I was often relegated to little kid status. One night we had a group of people drinking at the bar and my boss, Patty, called me over and asked if I thought she should buy the group a round. She wasn’t setting me up or anything, just wanted my opinion. I actually think she was going to do it and just wanted me to agree. But my answer was, “No.” They hadn’t been there that long, the group wasn’t that big, and they weren’t spending much money. She was looking at the bar when I gave her my thoughts, and when I finished, she slowly turned her head to look at me it utter amazement. She kind of blinked her surprise away and said, “Huh, ok, good answer – thanks.”

The reason for her amazement was that I was certainly passing up more money by discouraging her from buying a round. I would have been tipped well if she’d sponsored a round for the group.

But while I probably lost money that night, from then on Patty knew that I was aware of what mattered for the business, not just my bottom line (buying rounds is tricky business from an owner perspective, and doing so needs to be done very selectively). She took me a lot more seriously, consulted me on increasingly important matters, and granted me a lot more latitude than other bartenders. This also translated into better shifts and the ability to make more money down the road. So I definitely benefited in the long run by showing her that what mattered to her, mattered to me, and I did so by passing on a few bucks up front.

You won’t necessarily have to forego money to show your boss that what matters to them matters to you, but give it some thought and see what you find. Many times it will create a connection with your superiors and cause you to be viewed as more of an equal.

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Tim Murphy is the founder of - the first free web app to help you track school and job applications.

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