Your Best Boss


best bossWho was the best boss you ever worked for?  Why?

I was recently leading a retreat with a number of executives: Presidents, VPs, GMs, Directors, and Managers of a wide range of companies.  The leaders ranged in age from 30 something to 60 something, with everything in between.

Our speaker, Drew Bird, was leading us in a session about the importance of Emotional Intelligence in leadership.  He put us into pairs and asked us to answer the questions I just asked you.

My partner and I had to scratch our heads for a while.  Hmm, who was the best boss I ever worked for?

I had to go back to the work I did between years at university.  In fact, both of us had to go back to that era of our lives.  During university I worked for a small landscaping company in Vancouver.  William Davies and Sons provided residential yard maintenance and landscape construction services.

Bill Davies was the sole proprietor of the company.  I was his second employee and his longest serving employee.  Bill was a character.  He definitely marched to the beat of a different drummer.  He did things differently.  Looking back, it’s not necessarily how I would do it.  However, he was the best boss I ever had.


Well, the reason for me was the same reason for my partner in the exercise.  In fact, it was the same for pretty well everyone in the room.

After our time of discussion in pairs everyone shared their findings with the group.  We were all in agreement.  These were some of the qualities we all came up with to describe those whom we deemed to be the best bosses we ever had:

They cared.  They were personable, empathetic, calm, supportive, engaging and encouraging.  They pushed themselves and they pushed us.  They went above and beyond.  They had a sense of humour.  They were trustworthy and transparent.  They identified qualities in us, and they believed in us.

Sounds kind of simple doesn’t it?  Over a dozen high level leaders all agreed that these were the qualities exemplified by the best bosses they ever had.  We could surmise that these are the qualities of great leaders.

I know for me, Bill Davies was the boss who cared about me more than anyone I’ve ever worked for.  He invested in my growth as a landscaper, even though he knew I was not making a career out of landscaping.  He saw who I could be as a leader, encouraged that in me, and placed me in positions of leadership.  He trusted me, trained me and entrusted me with responsibilities.

However, what impacted me most was how he cared about me.  He got to know me.  He invested in me.  He mentored me in life.  We did things outside of work together.  He invited me into his family life.  He invited me and my girlfriend (who would become my wife) to have dinner with his family at their home.  I got to know his kids.

He pushed me: whether it was felling my first tree with spurs and a climbing belt after a brief time of instruction in the shop, or his refusal to solve problems for me to teach me how to solve them myself.  I remember calling in from a job to ask what to do after my commercial riding mower had broken apart.  Bill simply said,

“Don’t bring me problems – bring me solutions.”, and hung up.

That profound leadership lesson I continue to share with the leaders with whom I have the privilege of working.

If you want the people you lead to tell tales of you as the best boss they ever worked for, then take a page out of Bill’s book:  Care.  Be personable, empathetic, calm, supportive, engaging and encouraging.  Push yourself and push your people.  Go above and beyond.  Be passionate about work and life.  Laugh at yourself and with your people.  Be trustworthy and transparent.  Identify qualities in your people and believe in them.

Who was your best boss?  Take some pages out of their book and perhaps you can wear the same mantel you’ve given them.

And by the way, thank you Bill Davies!

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Leading and Living on Purpose.