The crazy lengths companies will go to hire and retain high-level women

Companies that have both men and women in high-level positions see improvements in productivity, innovation, safety, and profitability. Yet the number of women with jobs at the top is still decreasing.

You know why you would not want one of those jobs: 80-hour weeks, monthly travel, other people raising your children. But I wonder if you know the incredible lengths a company will go to attract and keep a woman who has reached a top position. These are stories I hear from women I coach and companies who hire me to recruit the type of women I coach.

Coaching client: Managing director in investment banking in NYC.

Three weeks after the third baby, the nanny quit. The nanny was supposed to raise the kids til they went to college. But instead, in an unprompted exit interview from hell, the nanny said the house is chaos, the parents don’t get home on time and the family needs two full-time nannies and a chef if they want someone to stay in the job long-term.

Her husband was a deer in headlights. He hated managing one nanny so much as a stay-at-home dad that he went back to work. The idea of coordinating two nannies was too much. Managing two nannies, a housekeeper and now a chef—it’s a part-time job in itself.

She told her boss she was thinking of leaving. Word got out and three other banks offered her a job. Her boss told her if she would stay she could have any job she wanted. The firm would give her whatever accommodations she needs. They really need her to stay.

She quit so she could be home with kids.

Coaching client: Woman on track to be a partner at top NYC law firm.

When she had her first baby she got really efficient, but it didn’t matter because her firm runs on billable hours. The more efficient she got the better a deal her clients got. Her family never benefitted from her efficiency. By the second child, even with a stay-at-home husband, she had had enough. She never saw her first baby and she didn’t want that to happen with the second one.

She moved her family out of NYC and became an in-house lawyer at a company in Georgia. But she found that she was getting paid half as much money to do more than 3/4 of the workload she had before.

When she told her old boss the situation, he asked her to come back. She said she had to work remotely and she couldn’t go to the office every day. She wanted to be with her kids. He said fine.

Her husband is a stay-at-home dad, but she’s at home all the time, with very flexible hours. The firm makes sure clients assume she is in NYC. She goes to meetings in NYC once a month if there’s no way around it. At a recent performance review, her boss asked what she’d like to work toward next.

Her thought was: Nowhere. I just want to keep making this much money and being with my family. But she said, “I’d like to be work toward being made Counsel.”

The partner said, “Okay. You’re counsel.”

Certainly everyone in the law firm knows she’s can work remotely because she’s a woman. And now everyone knows she was made Counsel because she’s a woman. She doesn’t care. She says they would do it in a heartbeat for another woman at her level, but there aren’t any.

Recruiting client: Company looking for someone to lead a department of 75 engineers.

I don’t do a lot of recruiting, but often I get hired when the candidate is a very high-level woman. It’s a specialized talent to be able to talk her into taking the job, and I can help a company do that. Mostly because I know all the reasons why women don’t want high-level jobs. The board is getting called out for having no senior women so this position has to go to a woman. When the search went nowhere the company announced there is basically no salary cap.

Still, no takers.

Recruiting client: Company drowning under a pile of resumes for marketing VP.

The company wants a woman in this role. (Probably so the company doesn’t have to find a woman for the role of engineering  VP.) I look through the stack and I’m surprised to see almost every woman has listed at some point on her resume “Time off for children.” Apparently, HR sees this all the time. No one cares. As long as the woman wants to reenter the workforce, HR wants them.

I chose two women to interview. Both are super qualified, and both were absolute masters of the interview process.

But it turned out that each will continue staying home with their kids. I can understand that. I used to apply for jobs just to make sure I could still get one. Maybe one of them will start an interview coaching business.

Me: Why am I writing this anyway?

I spend a lot of time asking myself why I stopped giving speeches for $15,000 a pop. I told myself it doesn’t make sense to say no: even if I hate getting dressed up and getting on a plane, I can do one speech a month and it would be a good way to make money.

I called someone who used to book me a lot. He booked me in three hours. The world of top speakers is mostly men, and people are always looking for high-level female speakers. The date was five months away. I told myself that by then I’d be used to the idea of travel for work.

I didn’t get used to the idea. Because I don’t want to disrupt my kids’ days so that I can make a lot of money. But I did worry a lot that my decision was intellectually lame or spoiled of me or indulgent toward my kids or something else bad.

Hearing that other women gave up great opportunities makes me relieved. This is something that makes sense, on many levels, and that’s why the offers people make to women are so off-the-charts in generosity and flexibility. I wish I understood my situation better, though. I wonder: am I like the woman who keeps working because the job is relatively cushy or am I the woman who interviews with little intention of actually taking a job.

22 replies
  1. Lisa McLeod
    Lisa McLeod says:

    Wow! I had no idea. When I left corporate to start my own firm 25 years ago (after baby #1) women were expected to suck it up. Nice to know I could command anything if I went back, but of course, I won’t.

  2. harris497
    harris497 says:


    When the opportunity is right, you’ll know it intuitively… the problem is FEAR! Overcoming the fear of doing something new/different/”?demanding?” that takes you away from the boys is what you will be forced to face. I’m sending this post to my wife and daughters so that they know what is happening, because as Lisa stated before, “Wow! I had no idea.”

  3. Mark W.
    Mark W. says:

    Penelope, I think what you’ve got to be asking yourself is – How much do I want on my plate? How many things do I want going on at the same time? One speech a month doesn’t sound like much but when you add all the preparations including preparing the speech, travel, etc., it is more than at first glance. Also, you may be having flashbacks of being away from the kids too much when you were doing a lot of traveling getting seed money for your company, promoting your book, and doing speeches. And I think you attribute all that time being away from your family as a significant contributor to your divorce. Whatever the reason you’ll figure it out. So relax. Things have a way of working out fine.

  4. Tina Shang
    Tina Shang says:

    In law school we used to say they don’t make a job prestigious unless it sucks. I think women, who are still more socialized as caregivers, are more easily able to intuit that being a corporate elite in our extremely exploitative economic system is pretty meaningless and not fulfilling (not to mention destructive of families, local communities and the natural environment). I think men are starting to see this too, but have a harder time coming to terms with it as they are still more socialized to be providers. The baby boomers currently at the top of large corporations asking how to make climbing the corporate ladder appealing to the younger folks are asking the wrong question. It just isn’t.

    • Penelope Trunk
      Penelope Trunk says:

      I love this comment, Tina. Thanks for posting it!

      I think every word of this comment is so important, and anyone who is trying to put together their own career path right now needs to take into consideration all these trends. Most importantly, there is nothing great about the “great” jobs out there. There are very few people who were born to compete in such a hard-driving was as those great jobs demand.

      We know so much about why the jobs companies offer are inappropriate for the people who we are. But it’s hard to push back and try something else. It’s scary to go out on one’s own. There’s no benchmark for success. But still, I think Tina’s right that there’s no other choice.


    • Hrm
      Hrm says:

      Most high achieving men I know love it. Only ones I’m suspicious of have no friends or close family relations maybe just a dog. Then there may be work escapism going on but mostly the men I see high achieving feel so much satisfaction from it. Women the opposite. The more women pour themselves into work or beauty/thinness the more anxious and miserable they seem to me to be, and quite medicated. ThAt said being just a mom rarely satisfies women and you can feel like you’re going bonkers. I raised three alone and it was hard to work even Pt because invariably someone would get sick have heavy issues etc. now that they’re all almost in college I have to think about what will gratify me. My kids are all staying nearby. My oldest brings home his laundry! Such love!

    • MMJ
      MMJ says:

      I’m with you, Tina. I’ve had the prestigious firm jobs and inhouse jobs and they are OK – my current company is great though I’m a little tired of the role I play in it (but the firms were life-curdling places). But I keep meeting slightly younger women in legal settings who talk a lot about how “ambitious” or “ambitious and driven” they are. OK…towards what? Just towards things deemed “big” because that’s what we’re supposed to be ambitions/driven towards? They are never chasing anything I’d want or see as want-able… I just don’t get it.

      • Mel
        Mel says:

        Tina and MMJ have hit the nail on the head. The critique of the Lean In movement that resonated with me was, “Women don’t like what they are being asked to lean into.” Amen, sister! I’m a casualty of Big Law. These days, it never gets easier, even as a partner. Just more and more pressure to bill and to generate new clients. If you don’t want to play the game (or heaven forbid, your main client does a reorg or something), then you are out. Simply doing a good job for existing clients isn’t enough. My in-house legal dept. friends work very hard for less money and without much job security these days either. I do wonder how companies/firms will entice the next generation to take these jobs. I hope they change the rules!

  5. Maria Miccoli
    Maria Miccoli says:

    If you could get me those speaking gigs I would give you a nice percentage and hit the road. I have done public speaking before and loved it. Email me if you are interested.

  6. Hrm
    Hrm says:

    The dark side of affirmative action. Hire women minorities because you need a quota. I dont believe anyone on planet earth would turn down $15k a speech. Not believable. Clinton’s took hundreds of thousands so did Obama’s for vapid speeches. Easy street!!!

    • Penelope Trunk
      Penelope Trunk says:

      Well, you have to remember that someone who can make $15K per speech can probably make pretty good money doing something that doesn’t require travel.

      Something that comes up a lot in the coaching sessions I do is that when you look at someone who makes a good living from home, they probably took a huge salary cut to do that job from home (or they took a big risk to do that job from home). Nothing is “easy street”.


  7. Bostonian
    Bostonian says:

    I see you mention stay-at-home dads married to professional women. I guess we do exist after all. I just want to sea lion all over that.

    I have to laugh at that lame SAHD who couldn’t even even manage the kids with the help of a nanny. He needed two nannies and a chef? Seriously, what can the man actually do? I appreciate that story; it makes me feel very competent.

    It’s interesting that you counsel women in this situation. I wonder if anyone counsels the men. I honestly don’t get how other dudes don’t seem to like or be able to manage being in that position. I’m very happy.

    • Todd
      Todd says:

      I agree Bostonian! Completely lame that the SAHD couldn’t manage two nannies and a chef. I think he was just tanking his job at home so he get out of the house and work.

      • Bostonian
        Bostonian says:

        I remain full of wonder at this inability. Perhaps his office job was easier for him. I wonder what it was. In any case, his failure at home tanked his wife’s career. My wife’s career has taken off since I started staying home. I think that means I’m doing a good job. She calls me “two nannies and a chef” now.

        It’s so hard to avoid being sarcastic about this. Is it a failure of socialization? Maybe if someone had given this fellow a job as a babysitter when he was young he could have been successful as a stay-at-home dad.

        • Not that Melissa
          Not that Melissa says:

          It’s definitely a failure of socialization. I think instead of talking about how dumb that guy is (which is gratifying), it would be useful to acknowledge how hard taking care of a family is. Those of us who do it receive constant messaging that society doesn’t value us.

  8. Stephen
    Stephen says:

    Seems the whole “equality” line is and probably was always bullshit. This seems like pure advantage.

    There are men how could take these jobs, but they have to go to women and the men are victims of discrimination.

    However under our stupid social order this is viewed as progressive.

  9. Deepa Tanksale
    Deepa Tanksale says:

    One of the reasons the company would want to go to crazy lengths is because they have to do it to show gender diversity at work place. And ultimately whether to stay at home and raise a family is an individual decision. Women have to evaluate what makes them happy ,their priorities and whether they have a choice (social support, family support financial freedom). Some of us have a choice of saying no to lucrative offers and also the mental strength to make that decision. But if a woman is primary bread winner with a family to raise she many not be able to exercise such a choice. So it all depends on what an individual wants and whether life circumstances allow to do so.

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