CREATED WITH PERMISSION FROM THE REPRINT CL45.01 ISSUE. © KEY MEDIA FEATURE CROSS EXAMINED THE MEANDERING PATH FROM LEGAL TO CHIEF EXECUTIVE OFFICER Yves Desjardins-Siciliano always knew he wanted to head a company, but it took the new CEO at Siemens Mobility Canada years of persistence MAKING THE LEAP from general counsel to It involved uncertainty, short-term failures what a lawyer practising at a law firm would CEO is the stuff of dreams for many in-house and an openness to varied experiences. have received, including in marketing, sales, lawyers. While in-house roles are extremely Desjardins-Siciliano’s first taste of what felt finance and even installing computers. varied and often highly influential, many ambi- like professional failure was when he articled “I displayed the ambition to be a business tious GCs will ask themselves “what’s next?” at Stikeman Elliott LLP in Montreal but was executive at IBM, [and] the way to become an after leading the legal department. not asked back to the firm. executive at the time required that you carry For Yves Desjardins-Siciliano, the answer “On a personal level, it taught me to deal the bag, as they say.” to that question had been clear from the with failure, because I failed in staying at While Desjardins-Siciliano was settled outset of his career. He wanted to be a busi- Stikemans, [but I found] within me the confi- at IBM, one day he received a call from ness leader. In law school in the late 1970s, Desjardins- Siciliano attended a conference where Ian “I displayed the ambition to be a business Sinclair, chairman and CEO of Canadian executive at IBM, [and] the way to become Pacific, spoke. At the time, CP was a conglomerate of airlines, train lines, hotels an executive at the time required that you and other businesses. Sinclair, recounts Desjardins-Siciliano, carry the bag, as they say.” “talked about how being a lawyer had brought him to the head of this large Canadian dence to pursue my career objective and keep Stanley Hartt, a former partner at Stikemans, conglomerate. It inspired me to pursue my my eye on the long term.” who was working for the prime minister, legal studies with a view to becoming a busi- Desjardins-Siciliano took a role with a Brian Mulroney, at the time. Hartt asked ness executive. That’s how the whole the smaller firm in Montreal, but he soon joined Desjardins-Siciliano to become a chief of staff whole thing happened.” the corporate world at IBM Canada in 1982. to the minister of labour and minister of state Many years later in 2014, Desjardins- That, he says, was really the beginning of his for transport. Siciliano moved from a legal role to take on business education at “what I still believed to Desjardins-Siciliano wondered at the time the helm of VIA Rail Canada as president and have been the best business school.” whether leaving IBM was a good idea, so he CEO, and he is now CEO at Siemens Mobility IBM’s culture meant that Desjardins- asked his father for advice. Canada. But his path was anything but direct. Siciliano was given experiences well outside of “My father said to me [that] when your © 2021 HAB PRESS LIMITED, A SUBSIDIARY OF KEY MEDIA | TORONTO, ONTARIO | canadianlawyermag.com 12 www.canadianlawyermag.com 12-14_CrossExamined-SUBBED.indd 12 20/01/2021 3:34:15 AM CREATED WITH PERMISSION FROM THE REPRINT CL45.01 ISSUE. © KEY MEDIA THE MEANDERING PATH FROM LEGAL TO CHIEF EXECUTIVE OFFICER PROFILE 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 © 2021 HAB PRESS LIMITED, A SUBSIDIARY OF KEY MEDIA | TORONTO, ONTARIO | canadianlawyermag.com www.canadianlawyermag.com 13 12-14_CrossExamined-SUBBED.indd 13 20/01/2021 3:34:21 AM CREATED WITH PERMISSION FROM THE REPRINT CL45.01 ISSUE. © KEY MEDIA FEATURE CROSS EXAMINED government calls and asks you to act, just reached the end point he had set for himself SIEMENS’ RAIL, be thankful it’s not to hand you a gun. You in law school when he was appointed to a five- TRANSIT AND have to say yes. You can’t start negotiating; year term as president and CEO of VIA Rail. MOBILITY it’s your duty.” Heading VIA Rail meant coming full Desjardins-Siciliano stayed in government circle for Desjardins-Siciliano in two ways. Siemens has been providing solutions to until 1991, and he then joined an IBM subsid- His initial inspiration to becoming an execu- the Canadian transportation industry for iary to act as vice president, law and business tive had come from a talk by the head of the more than 40 years, including: development and then joined the legal depart- railway company Canadian Pacific. Also, in a ment at Bell Mobility in 1993. less positive light, he had helped institute a light rail vehicles in It was at Bell that Desjardins-Siciliano felt round of cost cutting to the rail service while Edmonton and Calgary he was ready to make the leap from the legal he was serving in Mulroney’s government. department to heading a corporation. While By improving rail service in a challenging trainsets that will be Desjardins-Siciliano patiently took on varying fiscal environment, Desjardins-Siciliano was delivered to VIA Rail starting roles for five years, by 1997, he was ready to be given the chance to reach his career goal in 2021 promoted to CEO. and help improve Canada’s environmental Unfortunately, Bell did not have the same impact. rail electrification of the light idea, and so Desjardins-Siciliano left. When Desjardins-Siciliano’s five-year term rail systems in Kitchener- Waterloo and Ottawa “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.” “I left [Bell] purely on a disagreement as to ended in May 2019, he felt satisfied that he career planning and my impatience to take on had made a real difference in improving the helm of the organization.” Canada’s rail system. So, he began what he Desjardins-Siciliano then worked as an thought would be his retirement. independent consultant for more than 12 However, just as COVID-19 hit in years. His ambition to be a CEO had been early 2020, a new opportunity emerged. thwarted by circumstance, and Desjardins- Desjardins-Siciliano received an offer to be Siciliano admits he questioned his decision CEO of Siemens Mobility Canada, which to leave. supplied technology and maintenance to the But for Desjardins-Siciliano, his decisions rail systems that VIA ran. This CEO position to leave BCE and IBM years before were would allow him to continue the momentum “key turning points.” While lawyers are often he had achieved at VIA to improve rail trans- trained to be risk averse and quitting your job portation in Canada. can be a tremendous risk, making these deci- “I really saw my job at VIA as a vocation. sions can also broaden one’s experiences. I could really see the need for greater, better, In 2010, a contact of Desjardins-Siciliano’s more efficient, simpler public transportation, time in government mentioned an opportu- because our cities are getting clogged. And nity as chief corporate and legal officer, corpo- we’re losing more and more time in solo- rate secretary at VIA Rail. So, Desjardins- driven cars.” Siciliano applied and got an interview with It was a vocation, it seems, that Desjardins- the chairman and CEO. Siciliano knew he wanted for a very long In 2014, Desjardins-Siciliano finally time. © 2021 HAB PRESS LIMITED, A SUBSIDIARY OF KEY MEDIA | TORONTO, ONTARIO | canadianlawyermag.com 14 www.canadianlawyermag.com 12-14_CrossExamined-SUBBED.indd 14 20/01/2021 3:34:20 AM.