Portrait of Michael Cherny
From Pivot Magazine

Michael Cherny is changing the face of corporate Canada

When Deloitte’s chief of staff came out as trans, he became a beacon of diversity on buttoned-down Bay Street

Portrait of Michael ChernyMichael Cherny, Deloitte’s chief of staff, national audit public practice leadership (Photograph by Katherine Holland) 

Sitting in a quiet Deloitte conference room on an early August day, Michael Cherny looks much like any other baby-faced Bay Street bro: carefully coiffed hair and perfect tan, dove-grey suit, large watch on one wrist, Fitbit on the other. His socks, a gift from his girlfriend, Caroline, are teal, with an amusing print of top-hat-and-bow-tie-wearing penguins—a sartorial wink that belies his otherwise buttoned-down appearance. Cherny, the chief of staff to the national audit public practice leadership at Deloitte, calls them “fancy socks.” He has the affable self-assurance and hundred-watt smile of a late-night talk-show host who’s just learned he’s been renewed for five more seasons.

If you’d met Cherny a year ago, he likely would have looked pretty much the same: similar suit, identical watch, comparable fancy socks. His hair would have been cut in more or less the same style. He would have projected the same confidence. But he would have also introduced himself, and been known to his colleagues and family, as someone else—Michelle. On Jan. 8 of this year, his 28th birthday, Cherny posted a photo of himself standing in the Deloitte lobby to all his social media accounts. In it, he wore a grey suit, a blue tie, a huge smile and a button that said “Birthday Boy.” Accompanying the image was this message: “Hi, I’m Mike. And today is my first day living my truth.”

That truth—that Cherny is transgender—is something he’s known since he was about eight years old. But in the buttoned-down culture of Bay Street, it’s virtually unheard of for a high-level employee of a Big Four firm to come out publicly like Cherny has. His decision to do so marked a milestone for corporate Canada. 

Born to refugees from the former Soviet Union who settled in King City, Ont., Cherny was never comfortable being a girl. He just never felt like one. He didn’t yet have the language to articulate these feelings but they manifested themselves in ways that, retrospectively at least, were clear. He cried when he was made to wear dresses. He insisted on cutting his hair and shopping for clothes in the boys’ section. When he played sports video games, he would create player avatars for himself that were male. He always named them Michael.

The photo Cherny posted on the day he came out as transThe photo Cherny posted on the day he came out as trans (Photo courtesy of Michael Cherny)

If gender was somewhat confusing for Cherny, his sexuality was not. When he was eight, up late watching TV one Saturday night, he stumbled across an episode of The L Word, the lesbian soap opera. It was revelatory—female characters attracted to other female characters. Cherny realized that he felt the same way. He told his mother, who told him that it was just a phase, that he was too young to know who or what he liked. “It was a very common parent response,” Cherny says now. “But she just wanted to protect me. She came from a place where they would literally kill you if you were gay.” He came out, officially as it were, at age 19.

Lots of kids who question their sexuality and gender end up in the arts, finding careers or avocations that, theoretically anyway, encourage creativity, individuality and originality. Cherny’s inquisitiveness took him in a completely different direction—accounting and auditing. In high school, he took an accounting course and was fascinated by the problem-solving and the professional skepticism it required. “I liked the way it used my brain,” Cherny says. At the University of Toronto, he stuck with it, studying accounting with a minor in economics. 

At a Deloitte recruiting event in 2010, Cherny bonded with a partner over their love of golf and the TV show. The partner was in the mining division and encouraged Cherny to join as an auditor for a summer internship. Cherny was only 19 at the time and knew nothing about mining, but he was interested in private companies and entrepreneurship. He said yes. And then, ever the enthusiast, he again found himself smitten. “I loved that the work was tangible,” Cherny says. “It’s like, there’s a pile of dirt over there. There’s probably gold in it. You’re telling me there’s actually a million dollars of gold in it. I then have to find a way to prove that as I exercise professional skepticism about your assumptions.” 

Cherny joined Deloitte full-time as a staff accountant in 2012 and became a senior accountant in 2014, a year before obtaining his CPA. In 2016, Cherny was promoted to the position he currently holds, where he supports the firm’s leadership on the public side of its audit practice in Canada. “It’s like a wheel-and-spoke model,” Cherny says. “I’m in the middle and I work with my leadership on talent experience, quality—that’s the cornerstone of what we do in the public realm—which clients are we serving, which ones do we want to serve?” Cherny works with the various teams that operate in those particular spaces and ensures that there’s a consistent strategy among them. Ikram Al Mouaswas, a partner at the firm who has been, at various times, Cherny’s mentor, coach and manager, found him, from the beginning, unusually open about his identity, community and culture. “He’s passionate and intense, with really strong opinions,” says Al Mouaswas. “But he’s also good at taking in opinions that contradict his and accepting people asking questions.”

Deloitte had quickly proven itself to be a good home for Cherny, career-wise. But it was also, as he soon learned, a good place to be queer. By the time Cherny arrived at the company in 2011, it had a well-established group for its LGBTQ employees, Deloitte Pride Community, as well as separate groups for female, black and Indigenous employees, among others. Cherny became chair of the Pride group and, outside of work, also began to throw himself into non-profit work in the community. He volunteered for and sat on the boards of organizations like Pride Toronto, Start Proud (formerly Out on Bay Street), Toronto’s 519 Community Centre and the non-profit youth organization Ten Oaks Project in Ottawa.

 Cherny with his partner, Caroline, at a Deloitte Pride eventCherny with his partner, Caroline, at a Deloitte Pride event (Photo courtesy of Michael Cherny)

Lenore MacAdam, Deloitte’s national inclusion leader, started at the firm around the same time as Cherny and, like him, was involved with Deloitte Pride from the beginning. Five years ago, MacAdam says, she set out to make the “T” in the acronym more of a “reality” and began drafting Deloitte’s first set of guidelines for transitioning in the workplace (guidelines that include everything from the difference between gender expression and gender identity to ways colleagues can provide support). To her delight, she encountered no resistance, but there was a distinct and pervasive lack of awareness. She was asked why she was making such an effort when the company had no trans employees. “I would imagine there were lots of people here who had never knowingly met a trans person,” she says, adding that some people’s only reference point was pop culture. “When I first started doing this, someone said to me, ‘Oh, you mean like that character on Orange Is the New Black?’ ”

Deloitte released those guidelines three years ago, around the same time that the Canadian government was also making efforts at trans inclusion more broadly. In 2017, Public Services and Procurement Canada published “Support for trans employees: A guide for employees and managers” and Bill C-16 became law, updating the Canadian Human Rights Act and Criminal Code to include gender identity and expression. Less than a year after Deloitte published its guidelines, an employee came out as trans, and an inclusion survey the company undertook in the fall of 2018 revealed that, in fact, one per cent of Deloitte’s employees identify as trans. And MacAdam was pleased to see that, as trans employees came out at work, not only were their colleagues treating them respectfully, they wanted to fully embrace them. “I remember the first time that somebody was transitioning and I said to their leader, ‘Here’s something you could write to announce it to your team,’ ” MacAdam recalls. “They said, ‘That’s nice, but couldn’t we make it more celebratory?’ I was really impressed with the support and the joy.” Further demonstrating the company’s commitment, this past spring, it helped sponsor Canada’s public hospital transition-surgery program at Women’s College Hospital.

Cherny himself, in his role as chair of the Pride group, also helped a couple more junior colleagues transition. Nonetheless, he grappled for years with his own decision to do so. “I was afraid to use the word ‘trans’ for a long time,” Cherny says. Once, about six years ago, an ex-girlfriend asked him if he’d transition if he was on a desert island. A hundred per cent, Cherny replied. It was the impact on friends and family that scared him. And work: “In any company, you build a reputation. My biggest fear was that the perception people have of me would change. That I wouldn’t be viewed as someone who was good at their job, I’d be viewed as someone who had challenges or who was distracted.” 

Cherny’s fears weren’t unfounded. Corporate Canada is only gradually, and in some cases grudgingly, accepting new ideas around gender and gender expression. A couple of the major banks, such as BMO and TD, are updating application forms so clients don’t have to simply choose between two genders. “We do see firms trying to make accommodations and adapting,” says Sarah Kaplan, a professor at the Rotman School of Management and director of the Institute for Gender and the Economy. “However, it’s fair to say it’s very spotty. People are doing a few visible things but not all of the work needed to really include people of all genders.” She points out that only about nine per cent of the workforce is employed by firms as large as Deloitte and that the small- and medium-sized businesses that employ most people simply don’t have the resources to make the necessary changes to their cultures and infrastructure. Most trans people thus don’t have the accommodations they need at work: gender-neutral washrooms, say, or benefits that provide financial support for transition.

In Cherny’s case, though, it helped that he had support at home. Just over a year ago, Cherny started dating his partner, Caroline. A few days into their relationship, Cherny told her about Michael. She was immediately accepting. “If you talk to her now,” Cherny says, “she’ll say, ‘I always saw you as Michael, I only know you as Mike.’ ” He had already come out to his mother in the summer of 2017; last November, Cherny came out to his father—who, to Cherny’s amazement, was entirely understanding. “He just said ‘congratulations,’ ” and Cherny and his older sister, who’d come for support, started crying.

Portrait of Michael Cherny laughingAfter coming out as trans Cherny received hundreds of emails and about a thousand direct messages, uniformly praising and admiring (Photograph by Katherine Holland)

A few months later came Cherny’s 28th birthday, which he now refers to as “my first birthday.” The same day that Cherny uploaded his Birthday Boy picture on social media, Deloitte posted a profile of him to its internal website, in a section called “People to Be Proud of,” along with a separate notice from the regional service leader for the audit public practice that both advised colleagues on things like pronoun usage (Cherny prefers he/his) and was, like MacAdam had observed, suitably celebratory: “We deeply admire his courage and look forward to his continued leadership.” Over the next month, Cherny says, he received hundreds of emails and about a thousand direct messages, uniformly praising and admiring. His LinkedIn post alone was viewed about 400,000 times, and he received messages from strangers in Dubai, Ireland and South America.

In the notice from the regional service leader, people were also asked to be respectful and were encouraged to directly ask Cherny any questions they may have. This, as it turns out, was a blessing and a curse. Cherny welcomed the curiosity and was grateful for the dialogue—he calls it an “overwhelmingly positive response”—but it was also a lot to handle: “When I came out to my leadership, they were all like, ‘Great, we want to support you. How can we support you?’ That question is hard because there’s a lot of pressure and onus that’s placed on you as the employee transitioning to say, here’s what I need and here’s how it needs to happen.” To Cherny’s relief, inclusion leaders like MacAdam were able to have some of those conversations on his behalf. But the practical details of the transition also multiplied quickly and were likewise overwhelming: you have no idea how many places your name appears—from your email account to your insurance—until you have to change it. 

Then, of course, there’s the bathroom. Because of the design of Deloitte’s Toronto offices, it only has gender-neutral washrooms on the first six floors of the 44-floor building. Cherny works on the 14th floor. The day he came out as trans, he was between meetings and really had to go to the bathroom. He hesitated for a few minutes and then decided to use the men’s room for the first time. Both the stalls were in use. He went back to his meeting. A few minutes later, he went back again. This time, he was in luck, but on his way out, he bumped into a colleague whom he refers to as the most conservative person on his floor. “You do go through a bit of impostor syndrome where you feel like, okay, on Tuesday, I used the women’s washroom and on Wednesday I’m using the men’s washroom and how are the people around me going to respond to that?” But to Cherny’s great relief, his colleague’s response was completely gracious—that is, he treated it like no big deal.

While Cherny might have worried about people thinking he was distracted after he transitioned, the reality, he says, was that, for him, living in a woman’s body was its own distraction. Think about your brain as a computer, he says, with about 20 per cent of its capacity used for basic life functions—eating, sleeping, getting dressed—and 80 per cent for everything else. As a woman, before transitioning, he spent about half of that 80 per cent thinking about what other people thought about him, how he looked, how he felt. Constantly worried about outing himself, constantly focused on his identity. It left very little space for solving business problems. Now, though, especially as the tumult around his transition has quieted somewhat, he can focus entirely on his work: “My brain is quieter now.”