Good bosses sometimes get the short end of the stick. It's easy enough to recall details about terrible managers or supervisors — even many years after the fact. Meanwhile, a good supervisor can slip into the mist of pleasant, but foggy memories.
Today, for Boss's Day, we've asked six entrepreneurs and businesswomen about the best — and sometimes worst — bosses they've had. They share the impact those bosses had on them, how it changed the way they work or their career trajectories, and the lessons that the experiences imparted on them as they, too, became leaders.
Photo credit: Vanessa Acosta
"The last job I had before I left to start Jack Jones full-time was in marketing. I worked under a woman who found her power in making other people uncomfortable, and subservient. It was very important to her to know that someone else was ordering her lunch, bringing her dry cleaning, or doing her minor tasks. It's one thing to have an assistant, and that person does those things for you. It's another thing if having that is important for your identity. "But, when I was in college, I worked for a small, leather goods store, and I was employed by a Jewish woman named Mrs. C. and her husband, Mr. C. It was family-owned, and had been owned by their parents, and they were wonderful people. She gave me flexibility with my schedule because she understood that I was in school. Obviously, she had a schedule to keep — this was retail, and Christmas was really heavy, like any other retail space. But it was also very important to her that I do well in school, and she checked in on that. She never said anything like, Well, if you don't keep your GPA up, you can't have the job. It was more that I was ringing up expensive leather wallets, Montblanc pens, and Tumi luggage, and this woman was devoted to making sure that I did well. She understood that in two years, I was going to graduate from college and I needed to do a certain set of things with my life. "Mrs. C. also offered commission. We got our basic pay rate, which was well above minimum wage at the time, and again, is something I totally applaud her for. I know it's hard for small-business owners to pay well, and she always did. But if we sold a certain amount of luggage in a certain timeframe, we received commission on top of our check, and holiday bonuses. There was always an opportunity to do a good job, and to make more money for doing that good job. "She implemented a points system program, which was important to me, and for all the young people who worked for her, in which you would get a piece of luggage for however much money you [made]. When I left that job, I already had all the luggage I'd need, that I still use to this day. She would always say, 'A woman doesn't need diamonds. A woman who's going to be in the world needs good luggage.' This idea that you need luggage to get you around all the places you really want to go. She kind of instilled that in me. "I was able to go abroad when I was in undergrad, and I went to Spain for several months. Mrs. C. held my job, obviously something a small retailer doesn't have to do. She just took an interest in me as a person, as a student, and as a woman out in the world. She made sure that part of my edification was seeing the value in the small things I was doing now, that would set me up for the large things I would do later. "When I think about some of my own business practices, I think back to Mrs. C. because I think that giving a woman a job is not a feminist act in and of itself. That means you've done that woman a solid. Feminism is about empowering, and uplifting, and nurturing, and growing, so once you've given that woman the job, what kind of job are you giving that woman? Too many people are patting themselves on the back for just having signed a check. To me, where the feminist part of this all comes in is, how am I helping this woman see herself in the world?"
Photo credit: Scott Leon
Elle Huerta Founder & CEO,
Mend "There was a time early in my career at Google, right around the financial crisis, when there were team-wide layoffs. My direct manager and many of my peers were let go. Even though we were all briefed on the situation, it was still difficult and the morale of the remaining team was low. "I'll never forget the all hands meeting that one of our directors called. A lot of the conversations up to that point had felt stilted, but she was incredibly forthright about why the decision had been made. She also acknowledged how everyone was feeling, including herself, and it brought humanity to the situation for the first time. To me, it demonstrated the importance of transparency and authenticity in leadership."
Photo credit: Happy Family.
"As an entrepreneur and a boss, I am always looking to evolve, whether that be sharpening my management skills within our large organization, strengthening communication, or providing an environment where everyone can utilize their best and highest skill set. "Nearly 20 years ago, before I was my own boss, I worked at a media buying agency (very Mad Men style) and was tasked with building out the agency's new interactive division. I found myself working around the clock and putting in a lot of effort to make it something. I quickly learned that my boss and team did not share the same values, and that was a real turn off. I couldn't use my creativity to the fullest. I really want to admire people I work with every day, and always find a better way. "As a CEO and boss, I think it's incredibly important to set an example for your team, and live and breathe a real value system that people respect. It's about having a vision and mission that is bigger than me."
Photo credit: WP Narrative
"I'm in an interesting place [in terms of] having a boss for the first time in over six years, as my creative and tech agency, Narrative, was just acquired by Will Packer Media. It has actually been easier than I expected, as Will is a creative force, both collaborative and trusting. That kind of leadership has been a through line my entire career. "When I was fresh out of college, I worked as a sales exec at Emmis Communications, a storied and rather traditional media company. I had a boss there who just 'got' me. She never treated me like an employee, but rather as a mentor treats a mentee. She trusted that I would get the job done, and encouraged me to adopt an entrepreneurial mentality — to go beyond the job description. By giving me leeway to show what I could do, rather than prescribing what she thought I should do, I was free to push beyond the status quo and into the space where innovation happens. I was later tapped to build out the company's first digital department — back when everyone was excited to get an AOL account. That entrepreneurial mentality has bolstered and pushed me forward throughout my career."
Kristin Groos Richmond (left) with cofounder and CIO Kirsten Saenz Tobey. Photo: Revolution Foods
Kristin Groos Richmond
CEO & Cofounder, Revolution Foods
"When I was 25, I worked in Nairobi, Kenya, helping to start a school for children with learning differences. We recruited a new head of school, Janice Simpkins, who moved to Kenya from Pittsburgh. After watching me buzz around the school in a constant state of motion, attacking item after item on my checklist, she sat me down one afternoon to have a conversation. "She explained that over the years, I would likely learn that the presence and depth of conversation with my colleagues was far more important than 'checking' off my daily to-do list. She shared that she had a similar energy and approach at my age, but learned over the years how to build trust, teams, and commitment in her work through taking the time and presence to truly connect and show respect. "I have never forgotten the wisdom of Janice and her incredible guidance early in my career."
Photo credit: Gap Inc.
President & CEO, Old Navy "Early in my career, when I came to Silicon Valley during the first dot-com boom, I learned from a great boss that, simply put, the best idea wins. And arriving at the best idea requires diversity of talent and thought. It's not who has the winning idea — their level or seniority, gender, or race — it's the power of that idea to drive change, push boundaries, and enable growth. "At the time, the Valley represented disruption, innovation, technology, entrepreneurship, and out-of-the-box thinking. It was a place where I could dream as big as I wanted, and truly see what I was capable of. "The notion that 'the best ideas wins' is something I still believe and instill in my team at Old Navy. I surround myself with leaders who care deeply about each other and our customers, and who challenge the status quo in pursuit of a common goal: to create fashion for the people and disrupt the retail industry, one great idea at a time."
Photo credit: Mark Clennon
"In my most recent job, I worked at a startup as a marketing manager responsible for new user acquisition. In my short time there, I brought in over 700,000 new users to the platform in just 10 months. While employed at my then-full-time job, I also worked on establishing my startup, putting in 9-to-5 and 7-1 a.m. shifts to get things off the ground. I kept my startup under wraps from my bosses, and planned on telling them at the appropriate time. Since things were just starting out for my business, I didn't think [saying anything] was necessary — big mistake! "My bosses ended up finding out about my company via social media, and I ultimately ended up getting laid off. Although they never mentioned me starting a company as the reason for letting me go, I knew that was the case. Since I reported directly to the cofounders of the company, I expected some empathy, especially because they had gone through my exact process when starting their own business. "My advice for anyone starting a business while working a full-time job is to keep it a secret until you're ready to part ways with your company. In my case, I worked out a financial package and collected unemployment, giving me the time to focus on taking my business to the next level. Because of this experience, I've learned that it's important to encourage your employees who have aspirations outside of work, because ultimately, it leads to a happier work environment."