[9] Watson later moved to Ottawa to attend Carleton University and graduated in 1983 with a Bachelor of Arts in Mass Communications from the Faculty of Public Affairs.

[11] Watson began his career working in journalism for a few local newspapers, and later entered the federal public service, where he rose to the position of Director of Communications for the Speaker of the House of Commons.

[12] In addition, as part of the re-election process Watson donated his severance pay of $5200 to four local charities after moving from Regional to City Council in 1994.

[citation needed] In 1996, he supported Dalton McGuinty's bid to lead the Ontario Liberal party,[13] though at the time he still considered himself a "Red Tory", dating back from his university days when he was a member of the Progressive Conservatives.

[citation needed] He also championed a plan with two other councillors, Peter Hume and John O'Neil, to save the historic Aberdeen Pavilion from being torn down.

Watson has served on the board or as honorary chair of several community organizations including the Riverside Hospital, the National Arts Centre, the Central Canada Exhibition Association, the Christmas Exchange of Ottawa and the Forum for Young Canadians.

Watson worked alongside the Ontario Provincial Police (OPP) to create a "Fraud Free Calendar" in order to help protect consumers, particularly seniors, from high pressure sales tactics, which often lead to impulse purchases.

After a cabinet shuffle, Dalton McGuinty and Gerry Phillips implemented a money-back guarantee to individuals who do not receive a birth certificate within 15 days of the online application, which Watson had initiated.

During his tenure as Queen's Park's official liaison with Ontario's municipalities, Watson was able to implement substantive policies to alleviate fiscal pressure on cities.

Under this policy, the province took back $1.5 billion worth of programs funded by Ontario's municipalities, reversing previous downloading of provincial responsibilities which occurred during Mike Harris’ tenure as premier.

[34][35] Watson and the Ottawa City Council also invested $340 million in infrastructure renewal projects such as roads, sidewalks, pathways and sewers[36] and record amount in cycling initiatives.

[37] Watson helped advance two major city-building projects that had stalled for a number of years: the revitalization of Lansdowne Park and the introduction of light rail transit.

[38] In October 2012, the city council approved the final Lansdowne Park plan, an agreement with the Ottawa Sports and Entertainment Group that saw the existing stadium significantly renovated, increased green space, and housing and retail added to the site.

[45] A year later, on April 17, 2016, Watson led a delegation of 35 leaders in the business and tech industries to generate investment opportunities in technology, education, film production and tourism.

The mission's resulting list of Memoranda of Understanding (MOUs), strategic partnerships and mutually beneficial agreements between Ottawa companies and their Indian counterparts has an estimated total value of more than $80 million.

City council unanimously approved downtown Ottawa's second segregated bike lane in 2015 and built the 2.5-kilometre north-south cycling spine between Parliament Hill and Lansdowne Park on O’Connor Street.

[50] In addition, the NCC worked alongside Watson, as well as Nathalie Des Rosiers and Elizabeth Moore Aubin, to open another segregated cycling lane on Mackenzie Avenue, creating a safer environment for cyclists in the Ottawa region.

Over the course of year, the city played host to a number of successful events including the 2017 Red Bull Crashed Ice downhill skating competition, the Juno Awards of 2017; La Machine (production company), a four-day show that attracted over 750,000 people, Ottawa Welcomes the World, a series of celebrations at Lansdowne Park to promote tourism in other countries and strengthen ties with those nations, the 105th Grey Cup at TD Place, and the 2017 NHL 100 Classic, an outdoor game between the Ottawa Senators and the Montreal Canadiens that recreated the first ever NHL game almost 100 years later.

[57] He has also played an instrumental role to open a new central library to the city's downtown core at LeBreton Flats - a state-of-the-art net carbon zero facility.

[64][65] On Sunday, February 6, 2022, Watson proclaimed a state of emergency to handle a 10-day blockade as part of the Freedom Convoy 2022 that shut down much of the city's core.