Who Was Your Best Boss?

Who was the best boss you ever had? And why did you like them?

I have asked dozens of people these questions. It’s an interesting way to learn about someone and sometimes a good conversation starter. But I have noticed that I almost always get some version of the same answer.

The vast majority of people reminisce about a boss from early in their careers. Maybe it was a manager from their first professional job or perhaps from when they pivoted into a new role. What’s most consistent is that it was someone who really took an interest in helping them develop and grow. 

I frequently hear comments such as:

“He taught me skills that I still use today.”

“She advocated for me and helped me advance.”

“He gave me the opportunity to prove myself.”

“She took me under her wing and gave me advice and feedback like no one else ever has.”

Entering the workforce as a young professional or going through a career transition at any age is scary.  We are unsure what to do and feel unprepared. We don’t know the customs and practices of the team, which can include how to behave. Often, we don’t know how to even do the job. We are in a vulnerable and highly impressionable state. It’s no surprise that interactions with our boss or other people in authority during these times are so impactful.

I have a vivid memory from my first professional job out of college. I went into the first meeting with my new team and the VP of the division was there (which I didn’t understand at the time was a rare and special occurrence). He addressed the group about things going on in the business, and in the middle of his remarks, he looked at me and asked if I was going to write down what he was saying. 

I stared back at him blankly, as I had nothing to write with or on. He of course could see that.

“Always bring a pen and notepad to meetings. Don’t ever show up empty-handed again.”

I was mortified. I’m certainly not advocating public shaming as a management technique but will tell you I never forgot that lesson or experience. I wouldn’t say he was my favorite boss, but he made a lasting impression on me early in my career.

As leaders, we should be aware of the impact we have on others, particularly people who are new to our team, organization or their career. We should treat our ability to influence others with the seriousness it deserves. There are few things in life that are more meaningful or memorable than having someone stand up for you, teach you, push you, advocate for you or believe in you, particularly when you lack confidence or are unsure of what to do. 

I am often asked by young people who are just starting out for career advice. What do I wish I had known when I was their age? What should they do to be successful? I certainly have many pieces of advice to give them, many of which were lessons learned the hard way through my failures — starting with always bring a pen and a notepad to every meeting! It’s frankly flattering to be asked a question like that. It means that someone values what I have to say.

One piece of advice I give is fairly simple: keep asking questions – not just to me but to anyone you encounter who has had success in the area you are pursuing. What I have found is that more often than not, just like me, they will be honored you asked and happy to answer.

You see, all of us can recall a vivid memory of someone who invested in us. We know that if it wasn’t for that person – or more likely those people – we wouldn’t be where we are or who we are today.

If you’re entering the workforce or starting a new role, understand that the people you look up to remember the individuals who helped them when they were in a similar position. And likely, deep in their hearts, they want to be that person for someone else.

Here is a simple way to get started:

  • Identify someone you consider to be successful.
  • Have the courage to ask them if they’d be willing to spend a few minutes with you.
  • Ask them who their best boss was – and why.    
  • Find the lessons in their story.

      All of us stand on the shoulders of giants. The best way to show gratitude to those who came before us is to help others stand as well. There are few things in life that are as fulfilling.


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