The Collective Wisdom of High-Performing Women: Leadership Lessons from The Judy Project

By Barlow Publishing

How can women become effective leaders in large organizations without sacrificing who they are, as women and as mothers? This book answers the question: They should live out the 10 characteristics of today's winning leaders. These characteristics — compassion, honesty, and authenticity, for example — were once seen as feminine weaknesses in the command-and-control corporate world. But today, in an inclusive and connected world, they define the leader who strengthens organizations rather than undermines them. This book comes from the voices of experience: over 70 women who have participated in The Judy Project, a 16-year-old leadership forum for women leaders who are aiming for the top. In compelling, first-person stories, they talk about ambition, courage, and the hard choices they've made to manage personal and professional lives in the real world of business. They tell stories about how they put into action the 10 leadership traits, and they offer sage advice to young people — especially young women — about how they can move up in organizations while remaining true to themselves and to their families.

• Language: English
• Publisher: Barlow Publishing
• Release date: Sep 26, 2019
• ISBN: 9781988025476

Book preview

reality.

Introduction

Colleen Moorehead

Storytelling has long been used to pass wisdom forward from one generation to the next. And many of the storytellers are women … with children by the fire, in their beds, on their mother’s knee. This book is about storytelling. It’s about paying collective wisdom forward from one generation of female business leaders to tomorrow’s in order to sustain the societal change finally occurring in the workforce. It is written with optimism, and with the conviction that our future leaders — men and women — will value gender equality equally.

This is a leadership book full of stories by women who, during their careers, have truly lived the qualities of leadership that match their values. It’s not meant to be corporate speak from a podium, but lessons learned about 10 values-based traits that truly matter. These crucial traits aren’t textbook leadership qualities; rather, they reflect a more holistic concept of leadership: Courage, Honesty, Connection, Compassion, Energy, Lifelong Learning, Tenacity, Reinvention, Generosity, and Authenticity.

In these pages are the voices of women who have been part of a 16-year-old leadership program called The Judy Project. The program was named after a phenomenal business leader and friend of mine, Judy Elder, who died suddenly at age 47 of a blood disorder. She inspired many male and female colleagues; she was that rare sort of person who could create energy in a room. And she has inspired countless other people since, thanks to a powerful 2002 speech she gave about women and ambition. It went viral, and you’ll see why when you read it.

I was there. That day, in that speech, Judy defined an inclusive kind of ambition — one that, instead of representing greed and self-promotion, reflected a broader, more noble approach: ambition for her company, her leaders, her team and, yes, as an outcome for herself. So compelling was her articulation of a generous, collective, female ambition that when she died three weeks after giving that speech, a number of us were inspired to create a leadership program named after her, lest this new definition of collective ambition be forgotten.

Why was this vision of leadership so compelling? Because it contrasted so vividly with the heroic model of leadership: command and control. When I joined the investment industry in 1983, I was handed a book titled Dress for Success and directed to Harry Rosen’s for Women to buy three grey, black, or navy tailored suits. Like so many other women, I strapped on my combat uniform and joined a corporate culture that required women to adopt male characteristics, mannerisms, behaviours, and leadership styles if we wanted to succeed. We were told we were too soft. Our feedback in performance reviews was consistent. Be aggressive! Be more assertive! Be tough!

But this culture collided with women’s personal realities and socialization. We were arriving at the office after a total of three hours of sleep, with baby spit-up on our left shoulder and a to-do list that included dentist appointments, grocery shopping, and our children’s science projects. Although we women had no choice but to bring our whole self to the workplace, the only part of us accepted in the corporate leadership world was a traditional male business façade. Attempting to compartmentalize our divergent lives created such personal discord that many talented women were forced to walk away. They could not be honest or authentic leaders.

Command and control policies had been in place in many companies since the 1950s, when the men who ran those companies and created the policies had returned from World War II. This leadership style changed very little after women entered the workforce in the 70s: you were forced to make work the priority, and figure out how to accommodate the rest of your life around that. I was once offered a promotion that would involve moving from Ontario to Alberta; I said Yes! immediately, because I had to seem keen for the opportunity. Then I realized I hadn’t even asked my life partner what he thought. That’s how visceral the desire to succeed was whenever we had the sniff of an opportunity. It was a Pavlovian response.

Fortunately, an awakening was beginning. Company women’s committees became more prevalent. I vividly recall our small group of 16 or so senior women at CIBC in the early 1990s huddling together for warmth and survival as an HR consultant provided us with sensitivity training. She referenced the behaviour of our male colleagues as having originated from hunting meat as cavemen. This wasn’t exactly comforting, and it’s a concept we understand today as unconscious bias — something that has had a profound impact on the corporate world.

Over the next few years, the photo we had taken of our women’s committee came to tell the story of our working-life reality. One by one, a black X was marked over each of us as we left the frame: extinction through attrition. I myself became an X, leaving the bank in my eighth month of pregnancy, a casualty of another corporate reorganization.

My silver lining was my corporate rebirth thanks to a mid-1990s financial technology company called E*TRADE Canada, where the business culture was less prescribed. As with Judy’s experience, we were allowed to define a culture where celebrating our collective ambition allowed leadership traits such as empathy, generosity, and courage to surface.

* * *

The stories shared by over 70 women who have experienced The Judy Project are grouped in chapters about those 10 traits I mentioned above. These are widely recognized today as leadership characteristics that make our modern organizations stronger. When The Judy Project began, these were female flaws identified as weaknesses. The predominantly male corporate unconscious bias dismissed these emotion-based leadership skills, instead valuing the male-based skills predicated on toughness. It wasn’t really their fault; it was how they were socialized. Boys don’t cry. Keep a stiff upper lip. They simply transferred their unconscious biases to the workplace. But corporate culture has since evolved to embrace leadership attributes that match what millennials desire if they’re going to maintain themselves in the workforce.

Each year, the new cohort of some 30 Judy Project attendees introduce themselves to the women who will become part of the balance of their successful business career. They are asked to talk about one of their role models. Although these role models vary widely, from Margaret Thatcher and Golda Meir to recognizable corporate leaders, a solid 30 percent of attendees consistently identify their mother as the leader they most admire.

These women describe the collective attributes of motherhood as courage, generosity, selflessness, and unrelenting support and ambition for their children. Those traits are our unconscious biases. And that idea takes me full circle to what’s at the heart of this book. My mother had aspirations for me. And yours always wanted the best for you. But she didn’t necessarily have the opportunities you do. So she made selfless choices.

The stories in this book reflect what your mother would have advised if the framework were in place for her to succeed. This is the collective wisdom of 16 years of Judy Project alumnae, captured by 10 leadership characteristics. It’s storytelling learned from our mothers — and paid forward.

Through this book, we want women with aspirations of leadership to see that many successful women have had the same feelings you may be having — perhaps some sense of inadequacy, or a lack of confidence to talk about things that are gender oriented, like Is it okay to say I’m planning to have a baby in two years?

Those who follow the old autocratic leadership style don’t collect wisdom. They don’t stop to listen. So they don’t benefit from what others think. But in new kinds of organizations — the ones in which leaders collect wisdom from others as a rain barrel gathers drops of water — everyone benefits.

Will this new way forward stick? Nothing is certain. But I think it has a shot.

When Judy Elder talked about ambition, she made it clear that she was ambitious not only for herself, but for others as well. Judy’s style of ambition did not create winners and losers. She wasn’t fixated on climbing the corporate ladder for personal glory. She thought she’d win if everyone in the organization succeeded, and she was determined to make that happen.

In March 2002, when Judy was a senior executive at Microsoft Canada, she spoke about ambition to an audience of other aspiring women leaders as part of the Women’s Television Network’s Gift of Wisdom series. That groundbreaking speech, delivered three weeks before her death, created a legacy for female leaders. Here is an excerpt. (For the speech in its entirety, turn to page 219 at the end of the book.)

I want to talk about ambition. Freely, frankly, and nonjudgmentally. Which is not often the way ambition is thought about when used adjectivally with women. Somehow ambitious is right up there with aggressive when it comes to linkage with the B-word.

As I’ve thought more about women and their ambition, I’ve come to the conclusion that, in our society’s eyes, there are two sorts of ambition. First, and most applauded, is the desire for personal best — in sports, the arts, science, the professions.

But when it comes to organizational ambition, the passionate desire to lead complex organizations in business, government, and the public sector, we do far worse. We hold only 3 percent of clout titles — Chief Executive something titles.

Why is this so? Why are we celebrated for personal best but, dare I say it, blocked from organizational top-dog positions? Maybe because while women may be personally trusted, they are less trusted to lead us. We don’t have alpha people, we have alpha males. When it comes down to picking someone who is going to win for us, we are inclined to pick the big strong competitive, undistracted, yes, ruthless guy.

And this brings me to one of the best pieces of advice I was ever given. An early boss and longtime mentor told me once that people never get anywhere unless someone wants them to. Translation: Organizational ambition requires that others be ambitious for you.

Organizations are political. People quite naturally operate on the what’s in it for me? factor: enlightened self-interest. If they are ambitious for you it will be because they believe in your ability to help them achieve their goals. When people are prepared to go on dangerous missions with you, you know they’re ambitious for you because they see you as helping them win. Think of all the jerks who get ahead organizationally (the Enron leadership comes to mind). The reason they do so is because they bring others along with them.

I happen to believe that if you win for others along with yourself you will be rewarded with ongoing support and loyalty, and that loyalty will transfer from organization to organization, whether by reputation or, the truly to be cherished, people willing to follow you to other places. And by the way, I don’t believe you need to be a jerk to get ahead; in my experience, most jerks eventually get their comeuppance.

Frank Clegg

FORMER PRESIDENT OF MICROSOFT CANADA INC., CEO OF CANADIANS FOR SAFE TECHNOLOGY, AND JUDY ELDER’S BOSS AT THE TIME OF HER DEATH

Breathing Energy Into the Room

Frank, are you still there? my executive assistant in Toronto asked. It was 6 a.m. on the west coast when she called with the news. After a long pause, I finally replied. Yes, I’m here. I’m just trying to process this. But my stomach had dropped out. I was struggling to absorb what had happened. My GM of the consumer group, Judy Elder, had died. She was only 47.

And I didn’t even know she’d been ill. We’d had a talk three or four weeks back, when she was deciding whether to travel from Toronto to attend a big meeting at Microsoft headquarters in Redmond, Washington. She said she had something personal to attend to at home, but didn’t give me any details. I still wonder if I should have asked her for more specifics about what the problem was. But as a manager, do you pry into someone’s personal life? And I knew her well enough to know that she would seek input, and then make decisions herself. All I could tell her was, You have to decide whether this meeting is more important than whatever the issue is.

It turns out she’d been sick for a long time. Nobody at work had a clue about it. She had a blood disease and required frequent transfusions in hospital just to keep herself going. And her time had suddenly run out. The big thing that hit me was what a big loss it was … to the company, to the industry, to her team, to her network of colleagues and friends, and of course to her family, her boys.

Because Judy was one of the most special employees we ever had, and one of the best leaders. Some people are black holes: they suck all the energy out of you. Judy was the complete opposite. She injected energy into everything she did. Now, there’s a fine balance between being that person who is annoyingly rosy — the cheerleaders who don’t know how to turn it off — and that person who has credibility, and who can step back and take a breath. Judy had a real gift for energizing people appropriately and positively. Yet she wouldn’t gloss over problems.

A great leader like Judy is excited to see people do great things. She celebrated people, and mentored and encouraged them. I always thought she probably got up each morning and wanted to see what good things she could make happen. You could tell that quality was truly genuine and came from her heart.

Here’s an example of her generosity. There was one stage when I was completely distracted over a few days by a mini-crisis happening at work. Judy somehow intuited this, so when we had our regular monthly one-on-one meeting, in which we were supposed to talk about what was happening with her business, 90 percent of our time was spent on her helping me out with this issue. She knew I needed help, and she wanted to know what she could do. And not because I was her boss; she was that way with everyone.

Judy was intelligent and approachable, and one thing she kept saying was that there’s always a solution, and that we need to create an environment where people can come forward with solutions. She wasn’t way out in front pulling, nor behind pushing; she was marching right beside you. She got mud on her boots the same way you did, and she did that for people both senior and junior to her.

We had a rigorous mid-year review process, a check-in with head office to see how your line of business was doing so that the company could plan for the coming year. Judy not only had to do this for her own area, but I remember her taking the time to help someone who was struggling in their own area — on another team completely unrelated to her business area. I didn’t ask her to do that, and neither did the person she helped. That was how generous she was.

Her peers had the idea to create the Judy Elder award after she passed. One year, it was awarded to a seasoned manager in Ottawa. He had won Manager of the Year, another award we gave out, before that. But he called me after he got the Judy Elder award and said that it was the most significant award he’d ever received in his life.

I came to Microsoft when Judy was already there, and she and I got to work together for only one and a half years. And you know, to this day I wish I’d been the one to have had the honour of hiring her.

Cheri Chevalier

WORLDWIDE SALES LEAD FOR MARKETING TECHNOLOGY, MICROSOFT CORPORATION; WORKED UNDER JUDY ELDER AT MICROSOFT CANADA

Inspiring Others

In the short time I had the honour and privilege of working with Judy, she had a tremendous impact on me. Very soon after she started at Microsoft, we had our first real one-on-one meeting. Judy’s default assumption about me was that I had the potential to do great things. I think this was her belief about many of the people she met at Microsoft. She sat me down and told me that I hadn’t yet realized my potential, that I should shoot for the stars and think big — really big — and that I was amazing.

This, to be honest, was dumbfounding for me. She barely knew me, yet she assumed the best. She’d seen something in me and wanted to pull it out. It felt as if she’d placed her hand on my back, so to speak, and was gently pushing me toward where she thought I could and should be.

Looking back, I realize how important Judy’s encouragement was. You need someone with more experience to tell you what you do well and what you need to do better. You need someone to believe in you, help you see your talents, help you see all that is possible. Judy saw potential in me, and she gently fanned that ember before she passed away.

Judy has stayed with me from that moment on. It’s almost as though she’s a silent mentor, guiding me without words but fanning the flame she created through the memory of her confidence in me. I find I channel her often before big presentations. I lean into the vision she had for me. I push myself to see whether what she saw in me is really there. I feel her hand on my back.

And now I try to do the same for others. I try to push people beyond what they may expect of themselves and give them a vision for what could be possible and where they could go. I try to give others that same confident push forward so that I, too, can be the silent hand on their back. It has helped me be a better manager, and hopefully a better leader, too.

SHE SAT ME DOWN AND TOLD ME THAT I HADN’T YET REALIZED MY POTENTIAL, THAT I SHOULD SHOOT FOR THE STARS AND THINK BIG—REALLY BIG.

—Cheri Chevalier

There’s a lesson here on the importance of filling people with confidence by assuming their capability. When people lack confidence, they can get easily discouraged and down on themselves — and it’s hard to get them to be their best and do their best work. A word of genuine encouragement can stop the spin of someone’s self-doubt almost instantly. With it, you start to feel stronger, and you bring conviction and energy back to the table. And you start to do great things. Suddenly you have the energy to take on bigger challenges,