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Best.Boss.Ever.

I know! A lot of people don’t like the word “boss.” They think it sounds … well … “bossy,” as in “bossing people around” and “you’re not the boss of me!” and “I’m the boss so you have to do what I say.” I didn’t use to like the word either until I discovered that it can be used as a term of endearment.

When I was the director of an international school in China, many of the local Chinese staff referred to me as “Laoban” (boss). When leading teams in certain parts of the US many of my Spanish-speaking teammates would call me “Jefe” (boss). Even some of my English-speaking teammates have straight-up called me “boss.” None of those was being used derogatorily, they were used with genuine affection. So, I came to accept the word “boss” and even began to appreciate it because of what my teammates were communicating when using it.

Over the last 15 years or so I have used a specific question when I interview people regardless of the organizational level for which they were a candidate. That question is,

“Could you tell me about your best boss?”

I learned a lot about a person from their answer to that question. I learned, for example, how they like to be managed. But, I also learned a lot about great leadership from those answers. There are some pretty good bosses out there. There are some bad ones, too (I also asked people to tell me about them). But the good ones have these two things in common.

  1. They found a way to CONNECT with their people-as people.
  2. They were able to CHALLENGE their people to become and achieve more than they thought possible.

If you lay those two qualities down on a grid with CONNECT as the horizontal axis and CHALLENGE as the vertical axis, that will give you a 4-quadrant matrix that describes what kind of boss you are. The best bosses are well into the upper right quadrant of that matrix which is called “The Engager.” They CONNECT and they CHALLENGE.

When Leaders are Engagers, they have those qualities people use to describe their best boss. Do you want to be the best boss your people have ever had? Reply “boss” in the comments to let me know you do.

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