Before we get into today’s essay, two little important things!
I have a fundraiser for World Central Kitchen on my Instagram page to help with hurricane relief. You have to be on the app to donate but any support would be so appreciated. We are at over $10k!
My subscriber sale is going on through Sunday. Take 30% off a one year subscription. I think this only works for new subscribers. I don’t plan on doing another one for (at least) a year.
Today we are going to talk about old bosses! I tallied them up, and before going full-time with my blog and social media, I had seven bosses over the course of 12 years. I still think kindly of them. (Mostly.)
A few of my bosses were exceptional. Most were just doing the best they could. Managing people well is a tricky skill—it isn’t for everyone! To be totally honest, one of the reasons I knew the corporate world was not for me was that I would never want to manage more than one or two people.
My favorite boss of all time was my first: Alan Cohn. Alan was the women’s fragrance buyer for Filene’s (then a part of May Department Stores Company, which has since been absorbed into Macy’s). I worked for him during my first three-and-a-half years out of school, back when I lived in Boston. Alan is brilliant, charismatic, the best in the biz. At the time, he ran the second-largest buying department in the whole company. He’d been offered higher positions within the org but never accepted as he liked being a buyer.
He was larger than life and usually running late. I still remember my first day of work, when he and the other assistant buyer picked me up from our buying program’s executive trainee orientation. I was wearing an ill-fitting suit from Ann Taylor Loft (this was before the days of LOFT), a polyblend blouse from H&M, nude pantyhose, and uncomfortable pointy Nine West pumps. As the other trainees got “picked up,” I sat waiting like the kid whose parents were late for car pool. When he swooped in, I quickly realized it was worth the wait—I liked my new boss from the start.
To my 22-year-old self, he was a life-size Ken doll, with his mop of thick brown hair and blindingly white teeth. Still, his look—impeccable designer suiting and Gucci loafers—was quiet luxury before quiet luxury was a thing. This was 2003, when suits and pantyhose were required. Generally speaking, the buying office was not a bastion of style (buying is more numbers than taste) but Alan always brought his A-game.
I could tell you the funniest stories from the years I worked for him. Our team (two of us assistant buyers and an admin) was like a little family. The vendors we worked with were an extension of that. Every year, Alan and his partner hosted a gorgeous holiday party at their home. I remember admiring his silver and his china, thinking that it was the pinnacle of elegance. (It was.) At the party, and at work, I was just glad to be there. We worked hard, but there were days my cheeks hurt from laughing so much. His constant feedback on my outfits likely would not fly nowadays, but he saved me from some truly tragic mishaps and taught me the value of sizing up. He was extremely invested in my love life and finding me a “fella”; I constantly let him down.
I believe he was 42, which is funny as I’m now about the same age—older, actually.
My years working for Alan were the happiest and most fulfilling of my corporate-world days. (I break my career up into three sections: corporate-world, start-up, and self-employment.)
Directly, he taught me an incredible amount about business and life. I learned how to launch a fragrance brand in 100+ department store doors, how to negotiate hard (but still be friendly), how retail math works. But more than that, his actions modeled a good example for me. I learned that you could be a little unconventional, a little outlandish, and not only succeed but thrive. I learned how to manage and inspire a team, how to gracefully deliver bad news, how to motivate people.
Sure, I was spending the first half of every Monday sending faxes (again, a sign of the times), ordering lunch for the office, and making coffee runs, but I was also very young and fully involved in the business, given opportunities that other assistant buyers did not get.
Alan included me in every higher-level meeting he could. He’d prep me before and recap after, and would tell me it was his job to make me look good (in turn, I felt the same way about making him look good). When I was a fresh 24, he brought me along on store tours with the president and VP of marketing for a massive fragrance brand. I later found out he wanted me to have that exposure because he’d always seen me working on the other side of the business, in marketing for a fragrance brand. (And he pictured right.)
When Federated Department Stores purchased May in 2006 (this was the largest retail deal in history at that time!), he worked tirelessly to make sure I would be OK. He got me promoted to buyer-in-training early so that I’d have the resume boost. He used his connections to facilitate interviews and then a career move to New York, in marketing. Because of his advocacy, I was 25 years old and fending off multiple job offers. At his advice, I took a role at a fragrance company that had just been acquired by Procter & Gamble, slipping through the cracks into marketing at P&G—a total coup.
Alan was the best. The second-best boss I ever had was Rob, at P&G. Rob described his relationship to me as an “umbrella.” The umbrella stayed closed most of the time as he let me thrive and run my department—but when I needed protection, the umbrella opened, and he’d swoop in. He also instilled in me the idea of “being the duck”: calm as can be on the surface but kicking like hell beneath the water. Rob was great at metaphors.
The worst boss I had just wasn’t a people person. In today’s world, she would likely have been coached out of a management position and given a more siloed role where she could do her work (she was truly incredible at what she did) in peace without managing a team. Looking back on my experience, I mostly just feel bad for her. I could tell you wild stories. One day I’ll write a book and we’ll talk about it. Once she had me in the office until 9 p.m. velcroing bottles of pale pink nail polish to a foam board in order of opacity. Essie Mademoiselle is still very triggering for me. ;)
The second-worst boss I had was only happy to see me succeed if I stayed in my place (below her). She was my first boss in the city—an old-school beauty marketer used to hierarchy (and industry cattiness)—and I worshipped her at first. I ended up in a situation that would have resulted in a lawsuit in today’s world. Instead of suing and getting rich (lol) I just sucked it up and cried a lot. The lesson here for me was to stop the pattern. The women in my generation (and all the ones before) were often treated really badly in the workforce. That is no excuse for us to treat the next generation poorly.
The rest of the bosses were just doing the best they could. Like I said, managing people is hard.
I think, with time (and learning from past bosses, bad and good), I’ve actually become a decent manager. Here are some things I’ve learned over the years.
When hiring, at least for the sort of work I do, a good attitude is the most important thing. Everything else is trainable. I’d rather spend time training someone who is really excited to work with me than work with someone experienced but apathetic.
Managers have the power to affect their employees’ mental health. Really think about it. I have had nightmares about work and would never want to give someone else nightmares.
Run projects through your team first when prioritizing workflow. (i.e. before writing or editing photos, I send projects out to Carly or our graphic designer so that they have plenty of time to set up the posts, design the graphics, etc.)
Give people reasonable deadlines. I am still scarred from start-up life where “end of day” meant midnight and it was reasonable for my boss to ask me for something at 8 p.m. and want it by “end of day.” I work with a lot of contractors and I ask for their timelines up front. I always give as much time as possible and offer to pay a rush fee if I need something quickly.
On that note, use an email scheduler! I often work weird hours or on the weekend. Everything is always scheduled for the next day (or Monday morning) at 8 a.m.
It is easier to do everything yourself, but that is not scalable. Spending the time and money to train people who you can rely on is time well spent.
As a manager, you cannot expect those who work for you to care as much or work as hard as you do. It isn’t their company. (Yes, this applies even when you’ve given them equity.)
If you had a lousy boss, use that bad experience as a chance to reframe. Saying, “I put up with XYZ, so it’s fine for me to do it too,” is a terrible way to work. It is on us to make things better for the next generation.
Quick picks from the Shopbop Sale!
Everything I read last month. It was a disappointing month for books, but there were a few little gems.
How to style fall’s best tops! This was a fun one to work on. Hopefully, it inspires you to mix and match pieces you already own.
I finished Madwoman by Chelsea Bieker. This was a slog at first (and there is a huge, huge warning for domestic abuse— parts were hard for me to read, and this isn’t usually a trigger for me!). I wound up really enjoying it, especially the ending. A young mother seemingly has a perfect life, but everything threatens to come undone when she receives a letter from a women’s penitentiary. Solid B+.
I am embarrassed to tell you that I DNF’d the new Sally Rooney book, Intermezzo. It is a temporary DNF (I think), but the writing made me feel like I was reading jibberish. I feel… not smart? Honestly, after reading The Bee Sting, I require straightforward writing. I will pick it back up again, maybe this weekend, maybe not. sent me the below and it made me giggle.
Blue Sisters was next on my list and I can already tell you that I love this book. I’m only a couple of chapters in, though. The writing is fantastic and I love a book about sisters.
And of course the second it was available I downloaded Ina Garten’s memoir, Be Ready When the Luck Happens. This is a treat. I’m just about an hour in and already feel like I need to savor it. She’s had such an interesting life. I had no idea she worked for the government until she was 30.
With one exception, women bosses have been a huge disappointment for me. I work hard at doing better for the women (and men) I lead — giving them opportunities to do new things, to provide input on decisions I need to make (and actually listening to it), to have autonomy over their projects. I wish more women in leadership roles understood they look good when they cultivate talent.
This was so interesting! I've never managed employees, but my dad has had large teams under him and I've often heard him talk about trying to be a good example when it comes to work/life balance. He made it a point to always take a one-hour lunch break away from his desk and encouraged the people working under to do the same. He started and ended work at the same time every day and always stressed to his employees that if something wasn't done at 4:55pm, it could wait until tomorrow. No need to work late. He took all of his vacation days because he could.
I've rarely seen that attitude in the managers I've worked under.