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.
Absolutely agree. It's very unfortunate. No matter how many times I'd say "I'm not after your job, I want my own — will you help me get there?" A lot of the women I worked for perceived other young women as a threat and didn't want to help, missing the point that if we look good, they look even better.
Kelly, I’m 50/50 on this. The one boss I absolutely revered was a female manager and she was great at managing up, down, and keeping the team organized and motivated. The biggest takeaway I learned from her was to lead with compassion and empathy. It absolutely goes a long way. The worst boss I’ve experienced was also a female. I think organizational culture influences the management style too.
That is such a bummer! It really is unfortunately how so many of us feel like we have to be tough or feel like other women are only out to get us... I have so much hope for Gen Z and Gen Alpha. They seem poised for so much more equality and empathy than my cohort.
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.
I have a horrendous bad manager story that boils down to two things: upper management not being aware/not caring when being told, and no real training help for managers. Promoting someone and never checking in on them? Bad move. Luckily the staff is seasoned and we do what needs to be done, but it can be exhausting to train a new manager every two years.
#1!! YES!!! Also my rule is people are NOT robots. Lead with a People First attitude and they will be dedicated to the success of the mission and team. My turnover rate is incredibly low and I attribute it to this. I had great mentors and bosses and sounds like you did too!!
This is the #1 thing I’ve learned while managing. Support from above to help them shine, especially to the people above you. Trust your people and commit to believing they have good intentions.
One of my favorite coffee mugs is from the Alice Neel exhibition at the Met because the title of the exhibition was “PEOPLE COME FIRST.” I like to have my pre-work coffee in that during tough work times. :-)
Wow. Just. WOW. I am a fairly new people manager, and I've read blogs and articles and books, etc, but your post is pretty much the most helpful and digestable "how to be a good leader" content I've experienced. Thank you! I love the metaphors - the umbrella one kind of made me tear up, because that is exactly the kind of boss I want to be. And your advice about hiring for a good attitude - chef's kiss. Seriously, THANK YOU! I'm going to share this with my team. As a group of primarily younger women, I hope they will also find this valuable. <3
Thank you so so so much for this post. As a relatively new manager of around 10 people, I am constantly thinking through my leadership philosophy, skimming through leadership books I've read over the years, and taking lessons learned from good AND bad bosses. I love that managers are pretty much in the same boat across industries in terms of what we think about if we want to be good or even great!
I am also wrapped up in the discussion about bad women bosses. I am very well aware of these horror stories about women bosses, and know they do have a foundation in reality, largely because of how they were treated over the years and their inability to reframe their own thinking from those experiences to be better than how they were treated. *However* two of the best bosses I've had over the years were both women. They were amazing. I really just want to make sure that this trope finds an ending and that we don't keep repeating it as a problem just because it used to be (or still is in older generations), and then it becomes a self-licking ice cream cone. Let's give space to talking about the amazing women bosses we've had, and stop giving any energy or agency to negative talk about women.
I loved this. I am really struggling with a current manager and I feel like I’ve tried so hard to make it work. She seems to be someone who just isn’t the best people manager or maybe just not the best for me. Thank you so much for sharing. A manager can really make or break a role for anyone!
What a great recap! I’ve worked in finance my whole life and somehow have had a string of great to good bosses who have been incredible mentors, most of them men. When I had the chance to be manager I flopped and it really shook my confidence. However I learned a lot and also learned how to identify my strengths and stick with those. I do think good management ability can come with some time & experience.
This is such a lovely and valuable reflection to read! I had two of my early bosses at my 30th birthday tea party. I am very grateful to have worked for some women who are wonderful managers and people. Speaking of books! I just started The Friday Afternoon club by Griffin Dunn and I feel like many stripe-ers would enjoy it. He’s Dominick Dunne’s son and this is his memoir about growing up with all the stars from his Dad’s world, with a lot of heart and laughter, and some tears to come when he loses his sister, emotionally prepping myself already.
I've just borrowed Blue Sisters from a colleague after wolfing down Cleopatra & Frankenstein (have you read it?) a few weeks ago. So excited to get stuck in, especially after seeing it has you hooked already.
Co-sign on managers affecting one's mental health. My last corporate boss was a GVP at a cosmetics company— who clearly had been treated badly during her own career — who was lacking in any kind of self-awareness about NOT doing the same to her own reports. 2 years in, I was having major situational depression and anxiety — like, full panic attacks when I got on the elevator each morning. I have never been in a darker place professionally, and I promised myself to do better for my own reports and mentees, helping them plan their own progression, benchmarks, goals, etc. I try to give them the leadership I never had...plus corporate retail in fashion in beauty is simply ROUGH.
Love!! I’m almost 31 now and my best boss was my first boss when I was 23. I didn’t even know it then 😭 He would always do a check in every two weeks, and more likely than not we would just end up talking about unrelated work things. He was always there to advocate for me to higher ups during promotions and would encourage me to ask for more money. My pet peeve is managers who would message me “how are you doing?” And I knew they didn’t really care they were just asking me to do a task 🙃
First of all, you’re such an amazing writer — I love your storytelling. This piece resonated with me so much; YES, a good or a bad boss impacts you immensely and stays with you! And it’s so sad that your worst bosses were women and your best were men. Unfortunately I think that is often the case. When a boss is mistreated or under fire by the CEO, fight or flight kicks in and there is a huge tendency to then go hard on the people who report to them. And it’s often women who are under pressure and unfairly treated. I always found that when I experienced pressure or mistreatment, it made me feel better to be kind to the people who reported to me so they wouldn’t experience the same. That gave me a sense of control I was missing. I wish more people had bosses like you!
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.
Absolutely agree. It's very unfortunate. No matter how many times I'd say "I'm not after your job, I want my own — will you help me get there?" A lot of the women I worked for perceived other young women as a threat and didn't want to help, missing the point that if we look good, they look even better.
Kelly, I’m 50/50 on this. The one boss I absolutely revered was a female manager and she was great at managing up, down, and keeping the team organized and motivated. The biggest takeaway I learned from her was to lead with compassion and empathy. It absolutely goes a long way. The worst boss I’ve experienced was also a female. I think organizational culture influences the management style too.
That is such a bummer! It really is unfortunately how so many of us feel like we have to be tough or feel like other women are only out to get us... I have so much hope for Gen Z and Gen Alpha. They seem poised for so much more equality and empathy than my cohort.
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.
I have a horrendous bad manager story that boils down to two things: upper management not being aware/not caring when being told, and no real training help for managers. Promoting someone and never checking in on them? Bad move. Luckily the staff is seasoned and we do what needs to be done, but it can be exhausting to train a new manager every two years.
#1!! YES!!! Also my rule is people are NOT robots. Lead with a People First attitude and they will be dedicated to the success of the mission and team. My turnover rate is incredibly low and I attribute it to this. I had great mentors and bosses and sounds like you did too!!
This is the #1 thing I’ve learned while managing. Support from above to help them shine, especially to the people above you. Trust your people and commit to believing they have good intentions.
One of my favorite coffee mugs is from the Alice Neel exhibition at the Met because the title of the exhibition was “PEOPLE COME FIRST.” I like to have my pre-work coffee in that during tough work times. :-)
Wow. Just. WOW. I am a fairly new people manager, and I've read blogs and articles and books, etc, but your post is pretty much the most helpful and digestable "how to be a good leader" content I've experienced. Thank you! I love the metaphors - the umbrella one kind of made me tear up, because that is exactly the kind of boss I want to be. And your advice about hiring for a good attitude - chef's kiss. Seriously, THANK YOU! I'm going to share this with my team. As a group of primarily younger women, I hope they will also find this valuable. <3
Thank you so so so much for this post. As a relatively new manager of around 10 people, I am constantly thinking through my leadership philosophy, skimming through leadership books I've read over the years, and taking lessons learned from good AND bad bosses. I love that managers are pretty much in the same boat across industries in terms of what we think about if we want to be good or even great!
I am also wrapped up in the discussion about bad women bosses. I am very well aware of these horror stories about women bosses, and know they do have a foundation in reality, largely because of how they were treated over the years and their inability to reframe their own thinking from those experiences to be better than how they were treated. *However* two of the best bosses I've had over the years were both women. They were amazing. I really just want to make sure that this trope finds an ending and that we don't keep repeating it as a problem just because it used to be (or still is in older generations), and then it becomes a self-licking ice cream cone. Let's give space to talking about the amazing women bosses we've had, and stop giving any energy or agency to negative talk about women.
I loved this. I am really struggling with a current manager and I feel like I’ve tried so hard to make it work. She seems to be someone who just isn’t the best people manager or maybe just not the best for me. Thank you so much for sharing. A manager can really make or break a role for anyone!
What a great recap! I’ve worked in finance my whole life and somehow have had a string of great to good bosses who have been incredible mentors, most of them men. When I had the chance to be manager I flopped and it really shook my confidence. However I learned a lot and also learned how to identify my strengths and stick with those. I do think good management ability can come with some time & experience.
What a great write-up and topic! Thanks for sharing 👏
I loved this account of bosses it made me smile as for better or worse you learn a lot and especially how best to coach and mentor others.
This is such a lovely and valuable reflection to read! I had two of my early bosses at my 30th birthday tea party. I am very grateful to have worked for some women who are wonderful managers and people. Speaking of books! I just started The Friday Afternoon club by Griffin Dunn and I feel like many stripe-ers would enjoy it. He’s Dominick Dunne’s son and this is his memoir about growing up with all the stars from his Dad’s world, with a lot of heart and laughter, and some tears to come when he loses his sister, emotionally prepping myself already.
I DNF’d Intermezzo too, after loving her other books. Life is too short for me to spend any time inside Peter’s head, honestly!
I've just borrowed Blue Sisters from a colleague after wolfing down Cleopatra & Frankenstein (have you read it?) a few weeks ago. So excited to get stuck in, especially after seeing it has you hooked already.
Co-sign on managers affecting one's mental health. My last corporate boss was a GVP at a cosmetics company— who clearly had been treated badly during her own career — who was lacking in any kind of self-awareness about NOT doing the same to her own reports. 2 years in, I was having major situational depression and anxiety — like, full panic attacks when I got on the elevator each morning. I have never been in a darker place professionally, and I promised myself to do better for my own reports and mentees, helping them plan their own progression, benchmarks, goals, etc. I try to give them the leadership I never had...plus corporate retail in fashion in beauty is simply ROUGH.
Love!! I’m almost 31 now and my best boss was my first boss when I was 23. I didn’t even know it then 😭 He would always do a check in every two weeks, and more likely than not we would just end up talking about unrelated work things. He was always there to advocate for me to higher ups during promotions and would encourage me to ask for more money. My pet peeve is managers who would message me “how are you doing?” And I knew they didn’t really care they were just asking me to do a task 🙃
First of all, you’re such an amazing writer — I love your storytelling. This piece resonated with me so much; YES, a good or a bad boss impacts you immensely and stays with you! And it’s so sad that your worst bosses were women and your best were men. Unfortunately I think that is often the case. When a boss is mistreated or under fire by the CEO, fight or flight kicks in and there is a huge tendency to then go hard on the people who report to them. And it’s often women who are under pressure and unfairly treated. I always found that when I experienced pressure or mistreatment, it made me feel better to be kind to the people who reported to me so they wouldn’t experience the same. That gave me a sense of control I was missing. I wish more people had bosses like you!