National Boss’ Day

October 16 is National Boss’ Day  … a day that is often mocked as a Hallmark holiday.

According to Wikipedia, Boss’s Day was registered in 1958 so you could thank your boss for “being kind and fair throughout the year.”

In this day and age of layoffs, books about bosses who are jerks, and employees getting fired for posting inflammatory remarks about their boss on social media, it seems kind of quaint. But this day does make me pause and reflect on the bosses I’ve had in my career and all that I have learned from them.

I Walk In My Own Shoes

I assumed the best boss for me would be another working mom who would understand my struggles. I was wrong.

The female boss I had who was most like me (in terms of stage of life) was one of those Type A Superwomen. I had 1 kid, she had 3. I had a 6-month-old, she had an infant. She worked until the moment she gave birth, and then stayed completely connected all through her maternity leave. It was her choice, how she liked to do things, and it worked really well for her. But it made me feel inadequate for not being able to handle my own work/life balance issues when I wasn’t grappling with as many kids, or as much responsibility, as she was.

I made the mistake of thinking that someone who had walked in my shoes would automatically understand where I had been, and more importantly, understand where I wanted to go.

Even The Best Bosses Have Bad Days.

My most recent boss was great at acknowledging this; he would often come into my office the day after a bad day and apologize for his mood. The first couple of times I pretended that I hadn’t noticed, but finally I felt comfortable enough to ask what was up, which led to an even greater level of trust between us.

Bosses are not Mind Readers.

I thought my boss was there to tell me what to do. But I learned it was better to tell my boss what to do.

Bosses are not mind readers or long-email readers. I was in the habit of giving lots of information to my boss and assuming that he or she would know which outcome I wanted, since it seemed so obvious to me given my 14-bullet point explanation. Often I got no response, or a “Let’s chat.” Finally, one of my bosses pulled me aside and threatened me with bodily harm if I ever again sent a long, intricately crafted email or memo. “I trust that you’ve done the research and I want your recommendation. All that other stuff can stay in your file.”

I completely reversed my style, started my emails with my recommendation, including a few bullet points of ‘why’ and ended with “I’ll proceed forward with this as I have outlined, unless I hear differently from you.” Guess what? I was able to make a lot more things happen, much more quickly.

Who was your best boss? What did they do that you remember and value?

About the Author

Andrea Ballard

For 15+ years, Andrea Ballard, SPHR, has brought a unique, common sense perspective to the business of HR. A former HR Director and Training Manager, she advises companies on how to design/implement flexible work life programs to attract/retain top talent. A certified coach, she helps women create a balance between motherhood & career. She is the owner of Expecting Change, LLC, blogs at Working Mother and is on Twitter as @andreaballard.


Andrea Ballard

Debbie – I like your attitude – that the one you are working for now is the best!

Teresa and Heather – you both mentioned someone who didn’t micromanage. I think that says a lot about trust in the relationship and it was present for you both.

Debbie Brown

I enjoyed this post very much- honest and spot on-
My Best Boss is always the one I am working for, because I seek to learn from what that boss can teach me, and how I can help that boss be successful. I do not control whether they are good or bad- I appreciate what they are good at and learn from it… and take those lessons with me- I have learned from everyone I have ever worked for and around- and for that, I am grateful. (Sometimes I do think I learned more from the bad ones :)…and think that the lessons were good!

Teresa Rennie

My best boss was one who kept me in the loop, created a team environment and allowed me to tackle projects without micro managing me. She would review the status And then let me proceed.
I grew significantly in my profession under who tutelage and continue to keep in touch even though she is no longer my boss.
I learned that I could achieve greater levels of HR service and project management. I continue to this day to push myself forward and constantly look for ways to grow.


Best boss was the one who didn’t micro manage and just wanted me to see him if there were problems. He didn’t bother me with inane assignments and trusted my advice and feedback on situations in the workplace.

Worst boss was the one who had absolutely no sense of work/life balance. I wasn’t very busy at the job anyway because there were three people in the department for 200 employees, but I was expected to be there at least 12 hours a day even if I didn’t have anything to work on.


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