I bet you can list the things you like best – and least – about each of your bosses.  Bosses are powerful influences for better or worse, after all. I spent some time during a recent flight contemplating how many direct supervisors I had during my nineteen years in the insurance industry. Then I thought about what I did or didn’t appreciate about each. I ended up making a list of what made my three great bosses my favorites, and pondering how to impart their wisdom on others.

To give a little perspective, I counted fourteen direct supervisors in nineteen years, while working for three different Fortune 100 insurance companies.  Three of them…well, I couldn’t come up with much to appreciate. Eight were put into the “solid good” category (each had distinct leadership qualities and, for the most part, I genuinely liked them). However, there were three who stood out as absolutely great bosses.

Each of my great bosses showed up during pivotal points in my career, which I believe was perfect timing for me! The first, Laura, became my boss when I got my first promotion and moved into my first specialty position. The second, Jim, showed up when I took on my first real leadership position. I’d had “team leader” type positions, but this was my first official “manager” role.  Finally, the third (Ed) was like a beacon of light for me during my most significant period of transition – leaving Allstate, after fourteen years, to begin my first regional leadership position at Progressive, with responsibility for the Gulf states.

What was so special about my three great bosses?

  1. They were safe.
  2. They held me to high standards.
  3. They encouraged me.

Pretty simple. Yes, but clearly not easy, since only three out of fourteen embodied these characteristics.  Please allow me to describe a bit further:

They were safe.

  • They stood by me during triumph, and stayed with me during tribulation.
  • They were fierce opponents fighting for what was best for their organizations, but being under the protection of their umbrella was always a good place to be.
  • Their demeanor was predictably calm, solution/goal oriented, and logical.

They held me to high standards.

  • Working for them meant stretching, learning, and evolving: status quo was not OK.
  • Expectations were clear.
  • There were consequences for not achieving results.

They encouraged me.

  • Each understood there was more than one way to succeed, and they supported forging new paths to get there.
  • They were my biggest cheerleaders, in private discussion and public forums.
  • They made me feel abundantly capable, in part through presenting opportunities for greater exposure, allowing appropriate autonomy, and supporting personal development.

Each of my great bosses were well respected across organizational boundaries, and somewhat intimidating for people who only knew them by reputation. I got asked a lot what it was like to work for each. Without reservation, I give the same response today that I gave then – “Awesome!”

Whether you are new to leadership or a seasoned professional, I challenge you to consider what category you might fall into if your direct reports were asked:

  • Nothing much to appreciate;
  • Solid good;
  • Great!

If you’d like to make it to the “great bosses” ranking, I encourage you to seek out opportunities to demonstrate you are safe, hold your folks to high standards, and encourage them to become their very best.

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