On being named a Top 100 winner – the two women who inspired Caroline Riseboro

When I was told that I’d been selected as one of WXN’s Most Powerful Women last year my first thought was of my mother and grandmother —  two women who always serve as my original and continual inspiration, who were trailblazers in their own rights.

My grandmother came from a working-class family in England, and during the War she had to leave school at 14 to work. When she married at only 19, she was told she couldn’t work anymore. But she always knew she wanted a better life for herself, so with a tiny bit of money she started a business in the late 1950s and it became quite successful.

My mother was also a strong and brave business owner and always took chances. She was willing to constantly change and evolve to advance her career.

Both always pushed against the grain – and every day I try to channel that defiant spirit. Whenever I face barriers or feel deflated by the sheer amount of discrimination women and girls face around the world, I try to tap into that spirit and remember how far we have come. And how much we owe to women like my grandmother and mother, who were willing to defy normal and demand a fair shake.

I felt the award belonged to them.

This year, after receiving the honour once again (joining the Top 100 Alumni, made up of a stellar group of women) my first thought was of all the women I have had the pleasure of both mentoring and learning from throughout my career, particularly the incredible Plan International Canada girl ambassadors and advocates I have worked with over the last three years in my role as CEO & President.

Women and girls, who just like my mother and grandmother, continue to face barriers, hurdles, and glass ceilings when pursuing their dreams – despite it being the 21st century.

Women who dream of defying.

I read a quote by Steve Jobs recently that really resonated with me. “If you want to make everyone happy don’t be a leader, sell ice cream.”. Women and girls are always conditioned to be nice – to be liked above all else. This is something I have personally struggled with. At the same time, men and boys are taught that to change the world they should be prepared to ruffle feathers.

The women and girls I work with are constantly and unapologetically ruffling feathers. When normal is girls denied equality, they refuse to accept this status quo, they choose instead to defy normal.

But this can be lonely, often punishing work. That is why groups like WXN play a critical role in the advancement of women’s rights. Through my membership in WXN I have witnessed first-hand the incredible power of solidarity and sisterhood. It provides a space where us fellow feather-rufflers and defiant woman can come together and grow our strength and resilience.

As the inimitable Maya Angelou once said, “Each time a woman stands up for herself, without knowing it possibly, without claiming it, she stands up for all women.” Imagine the power women exercise when we knowingly stand up and stand together for our collective rights.

With my mother and grandmother behind me, I feel powerful. With a sisterhood behind me, I know I am unstoppable.

Join Caroline and become a WXN Member today. Witness the power and solidarity of the Women’s Executive Network to grow your career and expand your horizons.

About Caroline:

Caroline Riseboro, President and CEO, PLAN International Canada

2018 Canada’s Most Powerful Women: Top 100 Award Winner
CIBC Trailblazers & Trendsetters

Caroline Riseboro is the President & CEO of Plan International Canada – the leading NGO in Canada advancing the rights of children and equality for girls. As the youngest person to ever lead a major Canadian charity, Caroline is a passionate advocate for gender equality and is well-respected for her commitment to tackling some of the world’s most pressing issues.

She has a proven track record of leading organizations to new heights by challenging the status quo. In 2017, she was recognized as a Canada’s Most Powerful Women: Top 100 Award Winner and was awarded the Bronze medal in the Woman of the Year – Government or Non-Profit category at the Stevie Awards for Women in Business. Caroline regularly writes and speaks on the topic of gender equality and under her leadership, Plan International Canada has delivered record- breaking results.

Prior to joining Plan International Canada, Caroline was Senior Vice-President, Marketing & Development at the Centre for Addiction and Mental Health (CAMH) Foundation, and held many senior roles at World Vision Canada, more recently as Senior Vice-President of Marketing and Engagement at World Vision Canada. She was the first and youngest woman in the agency’s history to serve in this senior role. Before joining the non-profit sector, Caroline began her career in advertising and communications.

Caroline’s influence in the sector extends through her voluntary leadership roles. She sits on the Board of the Humanitarian Coalition and CAN-WaCH, is the President-elect for the Association of Fundraising Professionals GTA chapter, and has sat on numerous task forces including with Imagine Canada and the Canadian Marketing Association’s Not-For-Profit Council. She holds a Bachelor of Arts (Honours) degree from McGill University and is pursuing a Master of Philanthropy and Nonprofit Leadership from Carleton University.

You can reach Caroline on Twitter at:

Redefining Leadership with Disruption and Humanity

“Regardless of where you work or what you do, it’s really important to always change the way you approach things. . . .Redefining what we do and how we do it, shows the evolution of our society and its needs,” says Top 100 Winner, Ulrike Bahr-Gedalia.

In her recent insightful TedxKelowna talk, Bahr-Gedalia challenges us to redefine our traditional perception and understanding of leadership using two key qualities – disruption and humanity. The outcome, she says, can be extraordinary.

Bahr-Gedalia was joined at TedXKelowna by fellow Top 100 Winner Tasha Kheiriddin – find her heartfelt talk on how autism can make a better world here.

WXN Digital Brand Ambassador Ilona Dougherty is Wired for Innovation

Do you remember your first summer job? What it felt like to come to the office every day instead of going to school? How grown up it seemed?

Our first jobs often make lasting impression on us. But in a world that portrays Millennials and Gen Z as a nuisance, are we giving young people the opportunity to make a positive impact on the workplaces they will frequent this summer?

Recently at the University of Waterloo I give a Tedx talk about how our summer interns and young employees are in fact the innovation engine our companies need in a knowledge economy. Neuroscience and developmental psychology tells us that from 15 to 25 years old young people’s brains are wired for innovation. They don’t need to be trained or taught to be innovative, we just need to tap into their natural abilities.

This summer I encourage you to look at the summer interns and young employees you are working a little bit differently. If you let them, they can have just as much of a positive impact on the work you do, as your mentorship and support will have on them.

For more tips and insight about how to tap into young people’s potential in the workplace check out my Tedx talk: https://www.youtube.com/watch?v=mobQ-r6k5xY


Ilona Dougherty is the Managing Director of the Youth & Innovation Research Project at the University of Waterloo (https://uwaterloo.ca/youth-and-innovation/) and was one of WXN’s Top 100 Most Powerful Women in 2015.


Overcoming the Self Doubt that Fuels Imposter Syndrome in Women

So here’s my dirty little secret: I’m an imposter.

There, I said it. It only took me 20 years, and lots of sleepless nights worrying about what other people might think. But now that it’s out in the open, the truth, I believe, will set me free.

What I’m talking about—for those business associates and friends who might be a bit nervous at this point—is the much-discussed “imposter” syndrome. That’s the phenomenon whereby high-achieving individuals think they don’t belong—that they’re a fraud and it’s only a matter of time before everybody figures them out. It’s an idea that’s been around since the 1970s, when a U.S. psychology professor by the name of Pauline Rose Clance started studying the issue amongst her students.

Back then, it was largely seen as a “women’s” issue. But since the study came out nearly 40 years ago, Clance and others have realized it’s something that men feel in equal measures—but don’t verbalize. I can relate. As the CEO and majority owner of a successful tech company, and someone who has served on numerous boards, I work mostly with men—men of varying levels of accomplishment and talent. But what unites them all, at least superficially, is an outward confidence that they belong.

On paper, I should belong too. I’ve lead Webnames.ca for 17 years—a profitable and growing company with no debt. We’ve built relationships with Fortune 500 clients around the world and have a widely admired corporate culture. I’ve won several local and national awards for entrepreneurship and leadership. And yet every time I walk into a room of my peers, my heart skips a beat and the nagging self-doubts resurface. Why am I here? Did somebody make a mistake in inviting me?

While the imposter phenomenon affects men and women in equal measure, what doesn’t strike with such parity is confidence. A recent Harvard Business Review article makes it clear: there is an undeniable “confidence gap” between the sexes, and it’s having a profound impact on who chooses what professions—and who ultimately climbs to the top. The problem is particularly acute in science- and technology-driven organizations like mine: of my employees, fewer than 20 per cent are women, including only one who actually works on the technical side of our business.

So what can be done about it—this confidence gap, this lack of female representation in the field, this feeling of “not belonging” for those who do make it to the top? I think the answer is three-fold. First, we need to find ways of encouraging girls earlier in life to believe that the maths and sciences is a viable pursuit. At Science World, data collected by UBC professor Andrew Baron indicates 26 per cent more boys than girls under the age of two are being brought to the facility’s Living Lab—that’s a decision being made by parents that has long-term implications. The school system also needs to create equal opportunities for excellence. In B.C., the provincial government has taken an important step by introducing mandatory coding courses into the K-12 curriculum—but teachers play a critical role too in ensuring girls get equal airtime, as boys are often quicker to put up their hands.

Secondly, companies need to go out of their way to attract and retain female employees. That’s something I’m hyper aware of at Webnames.ca, where just five out of every 100 technical job applications we get is from a woman. While an increasing number of employers offer flexible work hours and family-friendly policies to encourage women to stay and grow within a company, it’s not enough. We need to put women in leadership roles—and mentor them toward that goal—to ensure better representation within our ranks, and build clear paths for promotions and raises.

Finally, we, the female leaders of the business world, need to speak out more—to be both seen and heard. That’s what I’m doing. As a younger woman, I had a huge fear of public speaking. But I was determined to confront it, taking courses at the Dale Carnegie Leadership Centre to try to lick the problem. It still took another decade of pushing myself to accept those stress-inducing speaking offers. Now, I regularly speak to audiences in the hundreds—and with each passing speech, each passing year, it gets a little easier. I also make an effort to take on a young woman in technology as a mentee each year so they can learn from my mistakes and we work on planning out career/life goals


When there’s more of us “girls” sitting around the decision-making table, giving keynote addresses, or passing on our learnings, I think it’s only a matter of time before the confidence gap shrinks and that sense of not belonging starts to abate. But until then, we need face our fears head-on—and embrace our inner imposter.



Cybele Negris (cybele@webnames.ca) is president, CEO and co-founder of Webnames.ca, Canada’s original .CA registrar. She is also the founder of Webnames Corporate which specializes in managing large and complex domain portfolios for Canadian corporations and institutions.

Originally published in Business in Vancouver, February 2017.