Who Was the Best Boss You Ever Had?

July 2023

Identifying one favorite boss may be a challenge for anyone who’s been in the workplace for a long time with multiple managers who really shined. Yet some of us may struggle to rate any of our managers favorably. How about you?

If you’ve been lucky enough to have had at least one special boss, one you would have done anything for and would have gladly worked with forever, how would you describe the characteristics that made them stand out from the crowd?

If you’ve been a manager yourself, how do you think your own direct reports would define you? Would any of them say you were their best-ever boss?  Why or why not?

The opening chapter of my first book, The Wow Factor Workplace: How to Create a Best Place to Work Culture, was titled The Best-Ever Boss for a very important reason. Best-ever bosses are the lynchpin to creating “a best place to work.” Best-ever bosses guide and inspire their team members to be the best they can be at doing what they love.

When you don’t have a leader—or a coach or a mentor—who listens to you, cares about you, encourages you, inspires you, and takes timely action to help get roadblocks out of your way when needed, it’s unlikely you will ever be fully engaged in your role or love your job.   

Why isn’t every manager a best-ever boss? Is it really all that difficult to be one?

I’ve learned over the years that virtually anyone can be a best-ever boss, regardless of where they sit on the org chart, from team lead to CEO and anywhere in between. One simply needs to be a caring mentor who enjoys inspiring and giving those in their charge what they need to succeed and feel fulfilled.

Being a best-ever boss can be as simple as exuding a can-do attitude while playing to your strong suits and helping those around you leverage their strong suits—doing things they love and that give them energy.

That said, being a best-ever boss to everyone is not a one-size-fits-all endeavor. Because each individual has a different personality, needs, care-abouts, and strong suits, being a best-ever boss to everyone on your team may require you to engage differently with each of them. A style and techniques that resonate with some may not for others, so be flexible.

Some years ago, the corporation I worked for was acquired, which gave me the chance to interview for various new leadership opportunities. One which really excited me would potentially allow me to create a new division. The Vice President in charge was known as a mover-and-shaker on the fast track to the C-suite. Reporting to a woman with such a reputation intrigued me until several individuals who had previously reported to her warned me to steer clear.  

Forewarned but curious, I decided to meet with her and decide for myself. Surprisingly, I really liked her candid and forthright demeanor. I liked her vision and her open-mindedness about my own out-of-the-box ideas that could differentiate us from the competition. I knew instantly that we could work well together, so I took the assignment and never looked back.

Turns out, she was my best-ever boss. Here’s why: She gave me free rein to step outside the lines and break through every barrier that got in the way. She held me accountable for my commitments yet supported my every idea and effort. She freely offered advice and counsel yet let me do things my own way. 

Together we made a great team and had each other’s back. When she attended a multi-week executive education program at Harvard, she assigned me to be her backfill at headquarters.  When she got promoted, so did I.  I would have happily worked for her forever if she hadn’t eventually left the company. I learned a great deal from her, and I’ll forever be grateful for her caring mentorship.

I can see why some people didn’t resonate with her “high expectations” style, which she never varied, but which suited me perfectly. I simply proposed my plans and reasons for doing whatever it was I believed my organizations should do, and she simply held me accountable to achieve the goals I established for my organization. Clearly, not everyone is the self-motivated self-starter that I am, and those who need more direction may not appreciate being badgered when they fail to achieve the agreed-to objectives.     

Observing this, I came to understand that certain leadership styles inspire some people, but not necessarily everyone. I also came to learn that it’s the manager’s responsibility to flex their style to suit the needs of each individual team member, not the other way around. When a subordinate must defer to a manager’s standard operating procedure—whether it’s a “my way or the highway” or “fast and furious” or “you can figure it” or “get on my calendar and we’ll talk later” approach—outcomes are typically suboptimal.

One of the best-ever bosses I highlighted in both The WOW Factor Workplace and my second book, Heartfelt Leadership: How to Capture the Top Spot and Keep on Soaring was Britt Berrett, then-President of Texas Health Presbyterian Hospital-Dallas. Britt‘s organization was awarded not only “The Best Place to Work” by the Dallas Business Journal, they were also honored as one of the “Top 50 Best Places to Work in the State of Texas.”

Britt had this to say about best-ever bosses:

Transformational leaders get to know the team, understand the team, and invest in the team. Their results are superior.

When I lead an organization, I care so much about the people…. I hope as a leader I bless lives and unlock potential, and when they go home, they’re a better father, they’re a better mother, they’re a better brother, they’re a better sister.

I think great leaders are willing to invest because there is a higher calling and purpose in life. If we can collectively invest and be courageous, amazing things happen…. It requires you to have the courage to care about people and open yourself up, and do so in a very purposeful way, to bless their lives.

Transformational leaders draw people in by caring about them, caring about what they do, caring about who they are, what their hopes and their aspirations are. Sometimes it’s not revealed. Sometimes you’ve got to dig.

I’m there to help them and support them, to give counsel and guidance…I think because they know I do care for them, they trust me. I would never violate that trust.       

If you’ve ever had such a boss, then you know how your passion for your work and your performance evolved as a result.

If you’ve never had such a boss, the only thing stopping you from being that kind of boss is having the courage to care about your people and opening yourself up to being a blessing in their lives. Simply strive to be the best boss they’ve ever had. If you don’t know what that means to each person, then ask them.  

That’s my wish for you: Be a Best-ever Boss and help others do the same.

Just imagine the kind of world this would be if we all did that.