18 Boss Women Spill Their Oddest Experiences of Being a Chief

Success isn’t always welcomed with open arms. From condescending colleagues to insecure partners, boss women have seen it all. These real-life stories prove that no matter how high you climb, there’s always someone trying to downplay your success.

• I was leading a high-stakes meeting with executives when my soon-to-be ex-husband called—ten times in a row. Thinking it was an emergency, I finally picked up. He wasn’t in trouble. He just wanted to know where the air fryer manual was. In the middle of my pitch, I said, “Figure it out,” and hung up. The CEO laughed and said, “That’s exactly how you handled our last crisis—efficient and ruthless.” I got the deal. He got blocked.
• I work in landscaping and my crew leader—a tough, hard-working woman—is frequently assumed to be the owner's wife! And I’ve been asked a few times if I’m the daughter. We’re not that small of a company… Unknown author / Reddit
• I’m the manager of a nice coffee place, and for a while, I was the only female that worked there, with all the coworkers being these late-20s to early-30s bearded guys that, for the most part, I was younger than. Most of the guys I have worked with have been really cool, but I showed up to train one new hire who assumed that I was married to the manager. He apologized profusely. SchrubSchrubSchrub / Reddit
• I was a manager of a convenience store for a time, and to make matters worse, I was pregnant the entire time. My husband also worked at the convenience store and for the first few weeks I had the job as well as the month I was training. The entire time I was training, a bunch of people asked me what my husband thought of me getting a promotion and becoming his boss. Even after he left for his current job, people still asked me what he thought of me having the job. I was also quite shocked at the number of people who thought that me telling them to do their job meant I had become a “power-hungry so-and-so”. breentee / Reddit

• One of the people on my team tried to scold me for “showing him less respect than he deserves, as he is both older than me and male”. It was really funny to see his face when I high-fived the president of the bank and called him “dude”—which my team member had specifically objected to. Hawksinger / Reddit
• At a business dinner, I was sitting next to a senior investor when he turned to my male employee and said, “So, tell me about your company.” My employee, bless him, grinned and said, “Oh, I just work there. She’s the boss.” The investor laughed like it was a joke. I extended my hand and said, “Nice to meet you. I sign your checks.” He nearly choked on his drink.
• I've had a male subordinate who was doing poorly tell me he needed a new boss because I was “too much like his mom for him to respect.” He did not receive a new manager, nor did he keep his job. marxamod / Reddit
• My husband and I own and run a business together. In our articles of incorporation, we are 50/50 co-owners, and we work and make business decisions as a team. I don't remember exactly what we were doing, but we were at our bank setting up a new checking account or something. The woman behind the desk asked me what I did for the business, and I gave her a shortened version of my job duties. Before I even had a chance to wonder why she cared what I did for the business, she got to the same question for my husband. She didn't even ask him anything—I just watched her type “owner” into the text field. I told her that I was a 50/50 co-owner of the business. “Oh, it'll be fine,” she said. I made her go back and change what she put down for me. I am not going to be put down as “job duty” while my husband is put down as “owner”. Not only that, but I've put just as much blood, sweat, and tears into this business as he does. ShinyRatFace / Reddit

• At a networking event, I was chatting with a young guy who was clearly trying to impress me—until he realized I was the CEO. His face fell, and he stammered, “Oh, I thought you were someone’s wife.” I smiled and said, “I am. I’m also the reason you’re here, since I own the company that’s hiring you.” He went pale and excused himself to get another drink. The best part? He didn’t get the job.
• A former boss of mine once answered the phone for a call from a B-to-B salesperson who asked to speak to the manager. She said, “This is she. What can I help you with?” I could hear the guy on the other end practically yell at her, “you’re obviously not the boss, you’re a woman!” Before he hung up. Hilarityt***rror / Reddit
• I used to be a supervisor for a small department. Sometimes, I covered the phones for the receptionist when she took lunch. People treated me very badly when I was covering that job. One time, a guy called and angrily asked to speak to a supervisor. I said, “I'm the supervisor of (that department).” He said, “NO, YOU'RE NOT! What is your title?” in a nasty tone of voice. I told him I was the supervisor of (the department). I was shocked that he called me a liar right to my face, so to speak. Unknown author / Reddit
• I have to be extra careful about my phrasing in emails. I have to throw in niceties, exclamation points, and even smiley emojis. Otherwise, I evidently come off as mean, condescending, and/or power-trippy. Like, I'm all for being polite, but what I'm talking about is above and beyond that. People of all genders react strangely to authoritative, direct communication from women. akath0110 / Reddit

• I once let a high school intern sit in on a meeting with me and a vendor. I swear to you, this dude was directing his pitch to a 16-year-old kid rather than to me, the person who would decide if we used his business. DietCokeCanz / Reddit
• My husband used to joke about me being the “boss” at work, but when I actually started making more money than him, the jokes stopped. One day, I came home to find him sitting in silence, clearly upset. And out from nowhere he said, “I just don’t like the idea of my wife being more successful than me,” he admitted. I stared at him and said, “Then you should try harder.” He didn’t. I left. My business thrived. He still complains to mutual friends.
• I work for a STEM company, and until recently (like, yesterday) worked in a technical management role. Interview candidates always assumed I was HR, even after being told who I was and what my function was. Male subordinates would be treated like my boss during interviews as well. Belfette / Reddit

• After college, my friend and I got jobs at the same company. After two years, I was promoted to team leader. Soon, I noticed strange things. My files would go missing, presentations would be deleted. I asked my friend to help me solve the mystery, and she told me that she would look into it. Later, another team member told me that it was my friend who was doing this, and sure enough, I caught her red-handed. Instead of apologizing, she blamed me for her behavior, saying I was being too “bossy” with her and was a bad friend. She even told me I shouldn't have taken the promotion. Needless to say, I got her transferred out of my team, and we aren't friends anymore.
• Not exactly a position of power, but a similar story. Once, a colleague of ours was introducing me and my boyfriend, to one of his friends. He went around the table, saying what everyone did for a living. When he got to me, he just said, “And she’s just a really nice lady.” My furious boyfriend yelled, “Dude, you know she’s an engineer,” and he just completely ignored it and kept talking. It was really bizarre, like he was unwilling to admit I was successful or (dare I say?) the most successful person there. SlothenAround / Reddit
• An intern once tried to explain my business model to me. I let him go on, fascinated by his confidence. When he finished, I asked, “That’s interesting—where did you get that information?” He puffed up and said, “Oh, I read about it online.” I smiled and replied, “I wrote that article.” His face went bright red. He lasted one more week.

If there’s one thing these stories prove, it’s that the workplace can be a circus and a scene for really brutal situations—especially when it comes to job interviews, clueless employees, and outdated attitudes.