4 Things I Learned From My Favorite Bosses

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The universe has conspired to make almost every boss I’ve ever had a woman in her late 50s or 60s.

From my first job working as a sales clerk at Knott’s Berry Farm to my first job in the “real world,” again and again I’ve come to find myself working under a woman who has seen and done it all. Some of these women have become not only my favorite people to work for, but also some of my biggest inspirations and sources of support as I’ve gone on to try and navigate my own career path.

As I’ve encountered different types of bosses in my life, those directly above me and higher, I started to wonder: what was it about my favorite bosses that made them so great to work for? What were the differences between them and those who I liked well enough, but didn’t make an impact? These differences are important to think about as I explore new opportunities, because they not only inform the decisions I will make about who to work for in the future, but also how I can adopt those qualities into my own workplace habits.

What I noticed was this.

My favorite bosses encouraged me to ask questions. When I began a new position, or took on a new responsibility, they wouldn’t get away with me confirming that I had no questions. They dug until I asked. They checked in and never made me feel like they were too busy to help (even though they totally were). They understood that as a young professional, I wanted to look like I already had it together—and they wanted to rip that habit out of me as quickly as possible. After long careers in which they made mistakes, and they had failures, they had the wisdom to know you should always ask the question that could prevent the mistake, even if you feel foolish for doing so.

My favorite bosses cared about my life outside the office. They showed up on Monday mornings and asked about my weekend before they opened their emails. They knew about my family, and about my relationships. I could tell them about my bigger dreams, and they wanted to help me see them through. They took the time to take me out to lunch, or invite me to happy hours. Some people may think this isn’t how professionals should interact in the workplace, but knowing that my boss saw me as a person instead of just a body on their team made all the difference in my workplace satisfaction.

My favorite bosses made me uncomfortable. Some jobs don’t leave a lot of room for learning new skills, but my favorite bosses made sure to help me find ways to add new items to my resume—even when it scared me. If an odd request came through, they’d ask if I wanted to take a shot at it, no matter my previous experience. They got to know about the things I was interested in learning, and created tasks (or asked me to brainstorm tasks) that would get me some experience in those areas. They didn’t want to keep me in the same role for as long as possible—they encouraged me to keep learning and growing, even if it would eventually lead me elsewhere. They pushed me to keep trying new things, because they knew my comfort zone would be the end of my climb.

My favorite bosses shared their own stories. The passing of stories and wisdom learned along the way is so valued within families and among friends, but making it a part of the workplace holds just as much value. Especially when you’re working for someone with much more life experience than you, the best thing your boss can do is share how they got to be where they are. Hearing about the failures, roadblocks, and successes of the women I looked up to reminded me that no path is linear, and no ending is permanent. When I was laid off from my first job after college, I remembered the stories my boss had told me about leaving her job in her 20s, moving to Europe to follow a man, getting her heart broken, and having to start all over again. Without knowing that she had gotten to where she was with failures and endings along the way, I would have been much more afraid of what came next.

I’ve been insanely lucky to work for some seriously smart, kind, badass women. And what I’ve learned from them above all else is to stick to your guns, stand up for yourself, and still remain a kind, warm, and genuine person in the process. I hope one day I’ll be able to return the favor.