Despite modest gains, women globally remain underrepresented in corporate leadership. To help accelerate progress and build closer connection and collaboration in Canada, 55 chief executive officers and presidents from diverse industries recently gathered in Toronto and Vancouver to discuss leadership. 

“We focused on women-specific content, supporting women CEOs to find new approaches to hurdles while enhancing individual leadership skills,” says YPO member, Executive Coach, former CEO of Juniper Park\TBWA, and chairperson of both events, Jill Nykoliation

Connected for several years via a WhatsApp chat group, most of the executives had never met in person. YPO member and President and CEO of GraceMed, Heather Shantora, had created the WhatsApp group in 2015, which has grown from 15 to 150 members. Despite its large size, the group still prioritizes intimacy and confidentiality, allowing participants to share openly business and personal issues. 

Women in leadership positions: A snapshot of the current landscape

October is Women’s History Month in Canada, a time to celebrate women who are contributing – or have contributed – to a more gender-inclusive Canada. Women currently make up a third of management occupations and 30% of senior management-level occupations. Just 4% of Canada’s largest publicly traded companies have a woman CEO. 

“In Canada, there is a lot of talk. But I am weary about the real impact despite evidence that shows that when more women are empowered to lead, everyone benefits,” says Geetu Pathak, a YPO member and Vice Chair of diversified investment company Ekagrata Inc. She cites research that confirms this. Globally, companies with higher levels of gender, ethnic and cultural diversity are more likely to outperform their less diverse peers on profitability.

Other Canadian research reveals how some women face more bias and receive less support at work because of their race or ethnic background. In one alarming statistic, it was found that women of color hold only 6.2% of women-held board, executive and management positions, collectively. 

YPO member and President of  Redwood Classics Apparel, Kathy Cheng, continues to witness this trend. “As an Asian woman in Canada, I’m often still the only woman of color at business events. But organizations are making an effort to try to diversify. I would not have been here if my YPO sponsor didn’t want me, intentionally. Intentional sponsorship is critical for organizations to advance diversity,” she says.

Key insights: What makes a good leader? 

The workshops covered two main topics. YPO member and Founder and Chief Impact Officer at Mission Wealth, Seth Streeter, spoke about developing a 3.0 vision of life, sharing how he personally rediscovered himself by looking at his life through 11 distinct dimensions. In the second interactive workshop, led by Executive Communication Coach at TalkAboutTalk, Andrea Wojnicki, the attendees explored how to define and activate their personal brands.  

The shared experiences and personal stories uncovered additional insights on how to advance leadership development.

  • Plan often and holistically. Regularly step back and assess what’s working and acknowledge areas in your life that may need more attention. For many of the CEOs, designing their environments and taking care of their physical bodies were low on the priority list. Create an action plan to address those areas.
  • Ask yourself, what’s next? Intentionally think about the next higher vision of yourself. “For a lot of women like me, in their later careers, with kids moved out of the house, transitioning into a new phase requires a different perspective, ” says Pathak.
  • Reframe your perspective of success: One of the dimensions presented by Streeter was the importance of creating impact and having purpose-driven goals. YPO member and CEO of One Girl Can, Natasha Questel, shared her path to a more fulfilled life by aligning personal passion with personal goals. “Last February, I left a lucrative corporate career to become a CEO of a nonprofit. While the YPO community has played a big role in this transition, the session was an opportunity to share my experience and a good reminder of the importance of leading more balanced, impactful and fulfilled lives as we move into that third version.” 
  • Intentionally define your personal brand. “How we show up, talk, negotiate and interact with others communicates who we are,” Nykoliation says, “Men normally brand themselves sooner and sharper. Women often have not gotten to it yet. In a nutshell, we should reflect on questions like “who am I, now?” Does my digital presence, headshots, and bio truly reflect that? Does how I choose to dress project what I intend? Everything speaks; it telegraphs who I am now and what I am uniquely good at.” 
  • Embrace your intersecting identities. Commenting on the importance of personal branding, Questel shared the challenges when coming from an ethnic minority background. “How to brand yourself seems like a simple model, but most of us find it challenging. This is not a topic we can discuss everywhere,” she says. “As an immigrant from Trinidad, a single mom and a woman of color, personal branding is something I always struggled with.” 
  • Be authentic.  “My company makes sweatshirts and T-shirts, so I tend to wear what I make,” says Cheng. “Eight years ago, I was less comfortable in my own skin and used to wear suits to work. Now, every day, I wear something that I make. It anchors me. And I learned that showing up to be me is part of personal branding.” 
  • Rethink rigid leadership style. The executives shared personal stories of a more inclusive, less rigid leadership style, one that respects collaboration and includes marginalized voices. Cheng adds, “I’m the president of the company but also a highly empathetic individual. The session reminded me that I can be a business leader and celebrate my EQ (emotional intelligence).” 
  • Embrace all forms of diversity. Key to the events success was the diversity of the women coming from different parts of Canada, as well as from different industries and life stages. Questel notes, “At my table, I sat next to a CEO 15 years younger and another 15 years older. There was a lot of wisdom in the room, and I found it invigorating to be with that mix.” 
  • Leverage women leadership networks in a safe environment. While women-only conferences and programs are on the rise, for many of the attendees, this was a different experience, with more sharing and faster bonding. “Having a group of business leaders — who are also aunts, sisters and mothers — is always special as we share the same empathy and don’t need to justify our emotions,” says Cheng. “Yet with YPO, there is a special bond, and it showed by how quickly we opened up.  The sharing is more generous. Subjects like menopause or perimenopause, miscarriages are normalized.” The WhatApp group was also key to quickly creating an environment of safety and trust.

Slow but steady progress

As the women executives headed back to their regions and companies, they left determined to apply and share the learnings and empower those around them. 

Within their communities and elsewhere, most of the participants shared stories of how they are already supporting the next generation of girls and young women. “Coming from a humble background, I am passionate about promoting girls’ education. Traveling to places like Kenya, I talk to vulnerable, high-potential girls in high schools, helping them find jobs, and providing inspiration to break barriers,” says Questel

Nykoliation adds, “For the past three years, I’ve taught a personal development class every Thursday for the employees in my own organization. Coaching the next generation through to executives about empathetic leadership – how generosity, gratitude and kindness can sit alongside more traditional aspects like achievements, targets and goals.” Her approach has been written about in FastCompany and is a case study in the Executive Leadership program at Harvard Business School. 

Attendees agreed that more needs to be done by various stakeholders to advance diverse women in leadership positions, but they emerged empowered, with new friendships and plans to make these events annual.

“Looking back from the original objectives, the meetings provided a lot more than practical tools and leadership skills. Perhaps more importantly, they provided emotional fuel for women, which comes through knowing that a community of women executives is out there supporting and celebrating them in their ongoing personal leadership journeys,” says Nykoliation.