He always knew he wanted to head a company, but it took him years of persistence to make the move
Making the leap from general counsel to CEO is the stuff of dreams for many in-house lawyers. While in-house roles are extremely varied and often highly influential, many ambitious GCs will ask themselves “what’s next?” after leading the legal department.
For Yves Desjardins-Siciliano, the answer to that question had been clear from the outset of his career. He wanted to be a business leader.
In law school in the late 1970s, Desjardins-Siciliano attended a conference where Ian Sinclair, chairman and CEO of Canadian Pacific, spoke. At the time, CP was a conglomerate of airlines, train lines, hotels and other businesses.
Sinclair, recounts Desjardins-Siciliano, “talked about how being a lawyer had brought him to the head of this large Canadian conglomerate. It inspired me to pursue my legal studies with a view to becoming a business executive. That’s how the whole the whole thing happened.”
Many years later in 2014, Desjardins-Siciliano moved from a legal role to take on the helm of VIA Rail Canada as president and CEO, and he is now CEO at Siemens Mobility Canada. But his path was anything but direct. It involved uncertainty, short-term failures and an openness to varied experiences.
Desjardins-Siciliano’s first taste of what felt like professional failure was when he articled at Stikeman Elliott LLP in Montreal but was not asked back to the firm.
“On a personal level, it taught me to deal with failure, because I failed in staying at Stikemans, [but I found] within me the confidence to pursue my career objective and keep my eye on the long term.”
Desjardins-Siciliano took a role with a smaller firm in Montreal, but he soon joined the corporate world at IBM Canada in 1982. That, he says, was really the beginning of his business education at “what I still believed to have been the best business school.”
IBM’s culture meant that Desjardins-Siciliano was given experiences well outside of what a lawyer practising at a law firm would have received, including in marketing, sales, finance and even installing computers.
“I displayed the ambition to be a business executive at IBM, [and] the way to become an executive at the time required that you carry the bag, as they say.”
While Desjardins-Siciliano was settled at IBM, one day he received a call from Stanley Hartt, a former partner at Stikemans, who was working for the prime minister, Brian Mulroney, at the time. Hartt asked Desjardins-Siciliano to become a chief of staff to the minister of labour and minister of state for transport.
Desjardins-Siciliano wondered at the time whether leaving IBM was a good idea, so he asked his father for advice.
“My father said to me [that] when your government calls and asks you to act, just be thankful it’s not to hand you a gun. You have to say yes. You can’t start negotiating; it’s your duty.”
Desjardins-Siciliano stayed in government until 1991, and he then joined an IBM subsidiary to act as vice president, law and business development and then joined the legal department at Bell Mobility in 1993.
It was at Bell that Desjardins-Siciliano felt he was ready to make the leap from the legal department to heading a corporation. While Desjardins-Siciliano patiently took on varying roles for five years, by 1997, he was ready to be promoted to CEO.
Unfortunately, Bell did not have the same idea, and so Desjardins-Siciliano left.
“I left [Bell] purely on a disagreement as to career planning and my impatience to take on the helm of the organization.”
Desjardins-Siciliano then worked as an independent consultant for more than 12 years. His ambition to be a CEO had been thwarted by circumstance, and Desjardins-Siciliano admits he questioned his decision to leave.
But for Desjardins-Siciliano, his decisions to leave BCE and IBM years before were “key turning points.” While lawyers are often trained to be risk averse and quitting your job can be a tremendous risk, making these decisions can also broaden one’s experiences.
In 2010, a contact of Desjardins-Siciliano’s time in government mentioned an opportunity as chief corporate and legal officer, corporate secretary at VIA Rail. So, Desjardins-Siciliano applied and got an interview with the chairman and CEO.
In 2014, Desjardins-Siciliano finally reached the end point he had set for himself in law school when he was appointed to a five-year term as president and CEO of VIA Rail.
Heading VIA Rail meant coming full circle for Desjardins-Siciliano in two ways. His initial inspiration to becoming an executive had come from a talk by the head of the railway company Canadian Pacific. Also, in a less positive light, he had helped institute a round of cost cutting to the rail service while he was serving in Mulroney’s government.
By improving rail service in a challenging fiscal environment, Desjardins-Siciliano was given the chance to reach his career goal and help improve Canada’s environmental impact.
When Desjardins-Siciliano’s five-year term ended in May 2019, he felt satisfied that he had made a real difference in improving Canada’s rail system. So, he began what he thought would be his retirement.
However, just as COVID-19 hit in early 2020, a new opportunity emerged. Desjardins-Siciliano received an offer to be CEO of Siemens Mobility Canada, which supplied technology and maintenance to the rail systems that VIA ran. This CEO position would allow him to continue the momentum he had achieved at VIA to improve rail transportation in Canada.
“I really saw my job at VIA as a vocation. I could really see the need for greater, better, more efficient, simpler public transportation, because our cities are getting clogged. And we’re losing more and more time in solo-driven cars.”
It was a vocation, it seems, that Desjardins-Siciliano knew he wanted for a very long time.
Name: Yves Desjardins-Siciliano
Current position: CEO of Siemens Mobility Canada
Previous positions:
2014-2019 president and chief executive officer, VIA Rail Canada
2010-2014 chief corporate and legal officer, corporate secretary, VIA Rail Canada
1997-2010 independent consultant
1993-1997 senior vice president, law, corporate development and secretary, office of the CEO, Bell Mobility
1992-1993 vice president, law and business development, ISM Information Systems Management (IBC subsidiary)
1989-1991 chief of staff to the minister of labour and minister of state for transport, Government of Canada, Ministry of Labour and Transport
1982 – 1989 various management positions in law, marketing and finance, IBM Canada
Siemens has been providing solutions to the Canadian transportation industry for more than 40 years, including:
