Who Has Earned a Place in Your Boss Hall of Fame?

Kris Taylor
3 min readMar 1, 2022

We all have “boss” stories. How we love to tell stories about those people to whom we reported! There is a cast of characters, ranging from the horrible ones, the clueless ones, the bosses from hell, and ones that cause us to wonder how in the heck they got promoted.

But my favorite stories are about the bosses that make it to what I call “the boss hall of fame.” The “boss hall of fame” is an imagined place — but it does exist in our heads and our hearts. It is a place of gratitude, reverence, and fond memories which get elicited as we recall those bosses that had a profound and lasting positive effect on our lives and careers.

I’ve been fortunate enough to enter more than a few people into the “boss hall of fame.” Here are some:

  • Dot, who was a no-nonsense and formidable woman, who was steadfast in her position that anything awry in the operation I managed was 100% up to me to address and fix
  • Steve, who saw something in me that I didn’t, and continued to put me in positions that stretched me to my max
  • Jim, who once he committed to something, steadfastly insisted his entire team see it through to the end, no matter how much pushback, arguing, or angst
  • Becky, who studied each and every person on her team and found ways to both nurture and challenge them to be their best

Here is the paradox about the bosses who make it to the hall of fame: you don’t ALWAYS enjoy every interaction with them. In fact, with my hall of fame bosses, there were many times I was frustrated, annoyed, and put out by them.

For these bosses see something in you that you don’t quite yet –and they keep putting you in situations that are outside your comfort zone.

Here’s what some of my best bosses did:

  • They challenged me, whether I was ready or not.
  • They found opportunities to teach me both the easy and the hard lessons.
  • They focused on results — and knew that worthwhile results come with focused and continual effort.
  • They finessed and didn’t force. None of my best bosses used intimidation or fear to motivate me.
  • They said yes to my “crazy” ideas, asked what was needed, and got out of the way.
  • They allowed me to make non-critical missteps and didn’t swoop in to rescue me.
  • They invested in me — by assignments given, conversations had, and development opportunities offered.
  • They shared how they thought about things and were interested in my perspectives

Here’s the funny thing. Each of my “hall of fame” bosses was different and approached their role of leader in their own unique way. Yet there are some common characteristics: they related to me as a whole person and not just a means to get some task done. They listened. They challenged. They set a high bar and didn’t take a lot of excuses. And they seemed to have a bigger vision about me and my potential than I did.

So I’m curious. Who would make your “boss hall-of-fame”? And more importantly, why!



Kris Taylor

Driving positive and transformative change though my writing and the three companies I’ve founded.