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?