Wingtips for Women: Success Without Compromise

Although we started the book with the focus on women who made it to the top of the sales organization, we soon discovered that many great women sales executives never made it to the top of the sales organization, not for lack of ability or success required, but often because they left to start their own companies and/or become CEO of a company. A success either way, I say. And a good fit for sales people, since both entrepreneurs and CEOs require fantastic sales and sales leadership skills.

My own story (see My Story page of this blog) includes a fast start in sales, reaching all the goals set before me, enjoying the award trips and celebrations, but then an exit to be a part of my first start-up. Going from selling at IBM where everyone knew we were ‘the safe choice’ to selling for a company that had not brand recognition and not even a full product yet, was a huge leap and demanded the best of what IBM had taught me about selling.

As we searched for the women we interviewed, we found more women who had been very successful in sales but who had taken those skills elsewhere. They had chosen to leave the corporate ladder and to apply their skills in a host of other environments from teaching to entrepreneurism to politics.

Two observations: First, selling is a skill needed in almost every job or walk of life—from motherhood to sales executive to CEO. Second, successful sales women, more often than not, can and do chose to ply their trade outside the narrow corporate track.

Why? The primary reason given was the life style and the money. Many of the women we spoke with chose to stay in sales, and not management, because promotions would cost them significant income opportunities and often increase the travel. Income and life style. Those who chose to move into other roles as entrepreneurs or who were recruited to run someone else’s company continued to rely on their sales skills to be successful, but their choices most often reflected a preferred lifestyle and income structure.

Think about it, male or female, what is not to love about the flexibility, the thrill of the chase, the money, the great awards and recognition of front line sales?!

So maybe there isn’t really a problem that there are so few women in sales executive roles, since many are where they are today by choice. Perhaps the real problem is that there are some extraordinary leaders and mentors in the chief sales executive role and because their numbers are so few, there are lots of Gen X and Y people who will miss the kind of leadership and wisdom they have to share.

But more on that later!

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Maybe this is a good time to back up and tell you a little about why we wrote this book. I say ‘we’ because if it takes a village to raise a child, it takes a city to write a book! The idea was birthed out of an innocent lunch in which my friends and colleagues, Laura and Daryl, jokingly (I thought!) suggested that one day I should write down all the things I had learned about succeeding as a woman in business and put it in the form of letters to my then teen-aged niece. The idea was to pass on the lessons learned to the next generation.

A couple of years passed and another business acquaintance suggested the same thing. I was beginning to get the message. When the third person gave me a numerical (data) reason to write the book, I knew it was time. The stats he quoted to me were astounding and compelling. His particular area of interest was women in sales. And his question was: If 25% of the people in sales are women, but only 1% of those women make it to top leadership positions in sales, where did all the women go? And why?

As I thought about this, I checked some other stats. It isn’t just sales leadership that is short on women; the shortage is in the board room and the C-suite across the board. And my mother thought her generation had waged and won the battles for career women of her daughters’ generation! Sadly, and fortunately for you, the frontiers are still plentiful.

The wonderful part of our pursuit of this book was learning that many women who have done well in their careers truly care about sharing their experiences with the next generation—and not just with women, but with men, too, who are climbing the career ladder.

So, while the women we interviewed for the book are each the top sales executive in their companies, the wisdom they share is mostly sales-neutral. That is, the lessons can be applied to any function and any organization, for-profit or not-for-profit, business or education.

The book is our way of helping you to learn from some extraordinary, yet ordinary, women who love what they do, who have made successful careers in the midst of a mostly male world and who have not compromised who they are as women, mothers, wives, mentors and executives. The book provides you access to women who know what it takes to reach the top rungs of the executive ladder without losing yourself.

Did we find out why so many women don’t make it? Not quantitatively, but there are some qualitative findings that we will share along the way.

Listen and learn from their experiences, the good and the not-so-good!

The book will be on Amazon in the next few weeks, so watch for Wingtips for Women coming your way. In the meantime, visit the blog as often as you wish and let us know what is on your mind. We want this to be a resource for you, not just a writing exercise for us!

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Not only do we speak different languages, but we also have very different expectations and lifestyles. Fortunately or unfortunately (you be the judge), young women and men just beginning their careers are not nearly so single minded and career driven as some of their elders. In fact, many are postponing even beginning their careers by taking on average 7 years to complete college (though I wonder if the current economic tide won’t change that!) or by traveling for a while before settling into a job. Even a job once taken, is often only for as long as it takes to find some new adventure or better opportunity. Loyalty, as Boomers know it, is a bygone tradition and thus requires a new way for Baby Boomer leaders to lead a new generation.

Gen X and Y workers have much to teach Boomers about how to enjoy life to the fullest without being the “dull boy” of the old proverb about Jack. (All work and no play, makes Jack/Jill a dull boy/girl!) In fact, many of the Boomer women in our book seem to have learned this Gen Y lesson far ahead of their generation.

What does this mean for the way Boomers share their knowledge with younger workers? Sometimes our expectations are not even on the same planet! Does being in the office or in front of a client meant that is the only time you are truly working? Or can you be working on your career while climbing Everest?

One of my long held beliefs is that executives who never take vacations, in fact, pride themselves on the fact, will see constantly diminishing returns on their hours at work. It was my husband who first taught me this while I was burning the midnight oil at IBM. I was in my early twenties and already not taking time to refuel my brain and my body. It is amazing how many problems can be worked out sitting on a beach or cycling down a Vermont road!

Alas, no single generation has it all figured out. These differences are some of the things we want to further explore on this blog, so please join us.

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As we interviewed the women for our book, we discovered that the way in which these women share their hard won lessons to the up-and-comers depended a great deal on the age and generation with whom they were sharing. Let’s face it; Baby Boomers speak a totally different language from that of Gen X or Gen Y.

It is somewhat akin to visiting a foreign country where you are supposed to be the visiting expert. The people you meet want to learn from you, but if you don’t speak their language, you can have the best intentions and the greatest wisdom to share, but it never reaches your audience. Without an interpreter or learning the language, the wisdom stays stuck in your head while your audience is craving to know what you know. A friend of mine says that is sort of like sitting on a ham sandwich starving to death! All the wisdom is right there in front of you, but you cannot access it.

One of the most enlightening things I learned about cross-generation communications is that young people no longer expect to “be seen and not heard.” They want to participate in the conversation, not just quietly listen to their “elders” expound on their experiences, no matter how great the lessons learned. They have great ideas and want to challenge and add to the body of knowledge from Day One. I don’t think they believe they are yet peers to the C-suite, but they do expect to be participatory in the learning conversations.

This is an area I would like to learn more about from our blog visitors—how do you think Boomers can best “speak” the language of Gen X and Y rising stars? As I said above, we can’t share our wisdom with each other if we aren’t speaking a language we both understand. That means making trade-offs and concessions to our favorite communications style for the sake of sharing ideas. What are your thoughts? What works and what doesn’t work, from your experience?

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Wingtips for Women: Success Without Compromise is a medley of stories, stats and advice from women who have reached the highest rungs of corporate life without compromising families and lifestyle and, who don’t mind giving kudos to the men and women who were the wingmen in their flight to the top. As with any good performance, the lead pilot cannot make the formation without good wingmen on both sides. If they don’t all work together, carefully observe each other and adjust for each other, they may all go down. Such is corporate life, and especially for women who have had relatively few leads to follow.

The 18 women we interviewed shared far more of their stories than can be contained in the pages of a short book, and so this blog will serve as a place to share more of their wisdom and stories. I hope it will also serve as a forum for sharing additional thoughts and guidance for each other across the generations of women at various levels on the corporate ladder. So please join us!

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