What Creates the Breakdown on the Road to Success?

By Mary T. O’Sullivan, MSOL

One of the highlights of my year, every December since 2015, is volunteer coaching at the Massachusetts Conference for Women (MCW) at the Boston Convention and Exhibition Center. However, in 2020, the entire event was conducted via Google Meets. Everyone missed the real life, human connections we made in person and the thrilling speakers and tremendous crowds, but there was a silver lining to not attending the conference in person this year. Because we could serve so many more women, instead of the usual 300 women per conference, we were able to coach over 600 women totally.

That meant that I had the privilege to personally coach over 40 women, one-to-one. It was truly a unique experience, with most of the women in the millennial age range. I was struck by how similar each coaching session was, and I found myself repeating the same coaching questions and advice over and over. These were all talented, smart, highly educated women, with incredibly attractive jobs. They were mostly from the tech field, but many were from pharma, insurance, banking, and the medical and legal industries as well. I was struck at how unempowered they felt in their work. How unappreciated, and how many of them worked long hours and were seemingly always expected to continue to do more. This pattern sounded so familiar to me, and I knew I couldn’t have been the first to notice it. After some research, I confirmed that I was not alone in my observations.

In his 2018 book, How Women Rise, Marshall Goldsmith and his co-author Sally Helgesen, point out 12 distinct areas where women efforts to move ahead breakdown. I was taken aback by how familiar these sounded after 20+ hours of coaching the women who signed up in my time slots. I’ve decided to mention six of them here today and will discuss the rest in a later blog post.

Here are six of 12 areas listed in How Women Rise:

  1. Reluctance to claim your achievements. The women I spoke to felt like they had to give credit to their whole team and felt guilty about bringing their personal achievements to the attention of management. Then they became very disappointed when they were passed over for promotion and not recognized for the work they did on a project.
  2. Expecting others to spontaneously notice and reward their contributions. This issue goes hand in hand with #1. My coaches were mostly reluctant to “toot their own horn”, feeling it wasn’t nice or proper, and then all their many hours and extra work should magically be noticed. The point is, the boss doesn’t care who did the work, they just want it done. If you don’t let the boss know what you did, he’s not a mind reader, you need to tell him.
  3. Overvaluing expertise. So many women stated that they had advanced degrees, even PhDs and wanted to continue on with a second master’s degree. They believed that the more education they had, the faster they could get ahead. When I asked how many degrees their male counterparts had, the answer 100% only a Masters; not two master’s and a Doctorate. Some technical fields do require a PhD, but not every manager had one. They were under the impression that if they more education, they would get the promotion or the special project. But when they thought about it, they realized extra education wasn’t always necessary.
  4. Just building rather than building and leveraging relationships. This belief was a hard one for these ladies to come to grips with. They all spoke of how they never thought of using their networks to help them move up. They were self-conscious about asking to develop a mentoring relationship, “just to get ahead”. They didn’t realize that a mentor’s purpose is to help their proteges to success. They were afraid to ask acquaintances about upcoming job openings. They felt it was rude, or even immoral to leverage people they knew to help them. When I asked them what they thought men would do, they laughed. They knew men would play golf, go for drinks, and hang out with guys from work in order to help their careers. I pointed out that women don’t games or workouts to socialize; they pack up their stuff and run home. The guys don’t.
  5. Failing to enlist allies from day one.  What is common practice on day one? Go through orientation, go to lunch, meet your boss and your team, and sit down and get to work? Or do you make friends with the others in your group? Do you make a point of getting to know people and where they are in the organization? Do you chat with other people in the women’s room, or do you just charge back to your desk to burrow into the next big project? The women I worked with didn’t understand how important it is to have a team behind them; to start off on the right foot, learn something about people and engage in both heavy work talk and friendly chatter. Find friends that can help you from the beginning and you can rely on them for the rest of your career. This seemed to be challenging for the MCW women.
  6. Putting your job before your career. It may sound ironic, however, when women burrow into the dirty details of the job, with blinders on, they can’t envision the big picture – called a career. If you desire the corner office, you have to show that you’re a leader. You have to take on something big and succeed at it. When the boss won’t give you that chance, you find another way. Volunteer for an outside charitable project and lead that! Lead a fund raiser for your church. Lead a clothing collection for the homeless, and get your picture taken with the head of the organization. Show what you can do. Once you’re pigeonholed at work, it’s tough to break out of that mold. People won’t think. You’re a leader if you hide behind your desk all day and always be “Miss Reliable.”

Once women are able to overcome these “limiting beliefs”, we can be more successful in the workplace. I’m not sure when it happened, but it seems like we’ve lost progress since the 1960s and 1970s. What ever happened to women standing up for themselves? How they’re treated and the response to that question is fodder for volumes.


Mary T. O’Sullivan, Master of Science, Organizational Leadership, International Coaching Federation Professional Certified Coach, Society of Human Resource Management, “Senior Certified Professional. Graduate Certificate in Executive and Professional Career Coaching, University of Texas at Dallas.

Member, Beta Gamma Sigma, the International Honor Society.

Advanced Studies in Education from Montclair University, SUNY Oswego and Syracuse University.

Mary is also a certified Six Sigma Specialist, Contract Specialist, IPT Leader and holds a Certificate in Essentials of Human Resource Management from SHRM.

(401) 742-1965