New NDP leader Jagmeet Singh, who started a cross-country post-leadership four-month tour last week to visit at least 14 cities, will use it as a key opportunity to boost the NDP's electoral fortunes in the next election. “As the old saying goes in executive search and recruiting, 'You never get a second chance to make a first impression,' ” said Robin Sears, an adviser for Earnscliffe Strategy Group. “This is going to be the first impression a lot of Canadians actually have of him , and it’s very important that it comes across successfully and that he’s seen as a credible alternative, particularly for progressive Canadians.” Mr. Sears said the “first challenge in politics is getting noticed,” and it’s something the NDP “hasn’t been getting much lately,” but a challenge at which Mr. Singh excels. Areas of the country where the NDP came close to winning in the last federal election in 2015 are part of the “organizational foundation” by which such leaders’ tours are classically planned, said Mr. Sears. The suburban and exurban communities around Canada’s biggest cities have become the real contest in federal politics, he said, and are likely to be in focus during Mr. Singh’s tour, in particular the Greater Toronto Area and British Columbia's Lower Mainland. On top of that, he said the tour will likely also be particularly geared, both online and in person, at reaching millennial Canadians, visible minorities, and new Canadians. Robin MacLachlan, a vice president at Summa Strategies, said Mr. Singh’s tour is an “incredible opportunity,” the main goal of which will be introducing the new NDP leader to Canadians. The fact that there are “a great many Canadians who haven’t yet formed an opinion about” Mr. Singh is both the NDP’s greatest opportunity, and it’s greatest challenge, he said. “He’s got a lot of momentum. He won on the first ballot, a very decisive victory. Only two NDP leaders have won on the first ballot: Jack Layton and Tommy Douglas, neither of them had a seat in Parliament at the same time, so those similarities make for a great narrative for Jagmeet Singh,” said Mr. MacLachlan. “ a great opportunity to introduce this energetic, relentlessly positive federal leader who’s got a remarkable story,” he said. Mr. MacLachlan said he expects the tour will be aimed at areas where the NDP already has a strong presence or a foothold, along with areas like the GTA where there is “probably the greatest opportunity for growth,” on top of being Canada’s largest media market. While he said he thinks Mr. Singh has quelled previously expressed concerns from the Quebec wing of the party by appointing NDP MP Guy Caron (Rimouski-Neigette-Témiscouata-Les Basques, Que.) as his parliamentary leader, and noted that the new leader has already visited the province, it will be smart for Mr. Singh “to go to Quebec early, and go to Quebec often.” Mr. Singh was elected the new NDP leader with 53.8 per cent of the vote in a first-ballot win on Oct. 1. While there’s no detailed itinerary yet available, the party has indicated Mr. Singh’s tour will be an intensive one and will end just before the party’s policy convention at the Shaw Centre in Ottawa in February. Mr. Singh’s tour will include stops in Toronto; Brampton, Ont.; Guelph, Ont.; Windsor, Ont.; Saskatoon; Regina; Halifax; St. John’s; Montreal; Sherbrooke; Que.; Vancouver; Victoria; Calgary; Edmonton; and more. He’s set to attend the Saskatchewan NDP’s convention in Regina on Oct. 27, and the B.C. NDP’s convention in Victoria on Nov. 4. Last week, Mr. Singh was in Toronto, Vancouver, and Ottawa. He attended the weekly caucus meeting on Parliament Hill and held a press conference in Centre Block with Mr. Caron on Oct. 18. This week, he’s expected to be back in Toronto and later in Saskatchewan. Mr. Singh also recently visited the riding of Lac-Saint-Jean on Oct. 9, ahead of the Oct. 23 byelection in the riding, to support the party’s candidate, Gisèle Dallaire, accompanied by Mr. Caron. The NDP came second in the riding in 2015, with former Conservative MP Denis Lebel, who resigned in June, having beat out Ms. Dallaire by a margin of less than five per cent of the vote. In the 2015 election, the NDP lost by a margin of 10 per cent or less of the vote in 22 ridings, of which 10 were in Quebec, seven in Ontario, two in B.C., and one each in Saskatchewan, Alberta, and Newfoundland and Labrador. In 14 of those ridings the NDP came second behind the Liberals, coming second to the Conservatives in seven ridings, and behind the Bloc Québécois in one. Post-election leader tours are commonplace in politics. Mr. Trudeau did it—with the help of specifically allocated party funds—after his election in 2013, and this past summer new Conservative leader Andrew Scheer criss-crossed Canada after his May 27 election. The importance, and potential opportunity, of such a tour is perhaps underlined for the NDP this time around. After being elected on the final ballot in March 2012, Mr. Mulcair assumed leadership of the then-official opposition party in the House. As a result, he was kept busy in Parliament in Ottawa, and his post-leadership election tour across Canada didn’t happen until the summer, after the House had risen. It’s since been described as the “best summer in NDP history,” as The Globe and Mail’s Jeffrey Simpson put it in an October 2015 profile of Mr. Mulcair. But during the 2015 election campaign, up against then-Conservative prime minister Stephen Harper and the new Liberal Leader Justin Trudeau, who’d been elected in 2013, the NDP, and Mr. Mulcair as leader, struggled with a lack of name recognition among Canadians. By comparison, Mr. Singh takes the helm of a third-place party, unencumbered by House of Commons responsibilities of his own, and unlike his predecessor, is the final new major party leader to be named. The fact that Mr. Singh doesn’t currently have a seat in the House of Commons is a “perceived weakness” that will be turned into a strength, said Mr. MacLachlan. “He’s going to use that time afforded to introduce himself to Canadians,” he said, aided by the fact “he has the benefit of a strong, 44-member caucus in the House,” something Mr. Layton didn’t have when he became leader. Mr. Sears noted Mr. Singh has already been busy in NDP trenches across the country, having worked on Rachel Notley’s campaign in Alberta, for Adrian Dix and John Horgan in B.C., and for the NDP in Nova Scotia. On Oct. 20, Mr. Singh resigned his seat as the Ontario MPP for Bramalea-Gore-Malton, Ont. Along with a cross-Canada tour, the new leader will also be carving out time to be on the Hill. Mr. Singh has attended both of the weekly Wednesday NDP caucus meetings on the Hill since being elected leader—with a break week between them—and each time held a subsequent press conference. Mr. Caron, the NDP’s parliamentary leader, said Mr. Singh’s attendance at the weekly caucus meetings will be a “regular feature,” happening “most of the time,” if plans permit. How these meetings run with the new leader isn’t “one size fits all,” he said: sometimes Mr. Singh will be there to “listen and reply,” or sometimes he’ll kick things off “stating what he’s been doing and where he’s going and then exchanging with the MPs.” Mr. Caron said Mr. Singh has indicated he wants to meet with each NDP MP individually to get a sense of their thoughts and concerns, and those meetings have already begun. Work on Mr. Singh’s transition in as a party leader without a seat in the House is ongoing, said Mr. Caron. As parliamentary leader, Mr. Caron said he’s in regular contact with Mr. Singh by phone, email, or text—or in person when Mr. Singh’s in town—so both stay up to speed. “He’s not micromanaging. What he gives us is a sense of direction of what he would like to see in terms of the philosophy to be followed, and then we are making a decision according to this,” said Mr. Caron. “Sometimes he will contact us to ask for advice, sometimes we are contacting him because we are asking for his advice … it depends really on what issues we are dealing with,” he said. Each recognized party in the House is allocated funds by Parliament to run a leader’s office, among other things, but use of those funds is “premised on the person being a Member of Parliament,” as explained by the House Speaker’s Office. As he’s not an MP, Mr. Singh is instead largely being staffed by the party, though some members of his campaign team are reportedly lending a hand to transition plans on the Hill. Melissa Bruno, Mr. Singh’s former chief of staff at Queen’s Park and an adviser for his leadership campaign, is in charge of the transition, and is now deputy chief of staff at NDP caucus services on the Hill. With any change in leadership, staff turnover is to be expected on the Hill. Mr. MacLachlan noted that members of Mr. Singh’s campaign team will also be a “breath of fresh air” at party headquarters, after proving their prowess with everything “from fundraising to digital communications to organization.” Since expressing his congratulations to Mr. Singh online on Oct. 1, publicly there’s been radio silence from former NDP leader Thomas Mulcair (Outremont, Que.), whose Twitter account bio still indicates he is “Leader of the @NDP.” Asked about what role Mr. Mulcair, who remains an MP in the House, would play in Mr. Singh’s transition and going forward, Mr. Caron said those discussions haven’t yet taken place as Mr. Mulcair has been abroad in recent weeks. Mr. Mulcair was in Andorra for meetings of the Organization for Security Cooperation in Europe from Oct. 1 to 9, and then in Russia up until the end of last week for meetings of the International Parliamentary Union. NDP MP Daniel Blaikie (Elmwood-Transcona, Man.), his party’s caucus chair, said thinks it’ll be a “priority” for Mr. Singh to be in Ottawa, particularly for caucus meetings, and one that’ll have to be juggled as his coast-to-coast tour of Canada is planned. While MPs are able to reach out to Mr. Singh themselves, Mr. Blaikie said as caucus chair he’s helping “set up conversations about important issues of the day,” and the two are “speaking often.” Mr. Blaikie said caucus is excited and “raring to go now” with a permanent leader in place. “We’ve been doing a lot of great work in Parliament over the last two years, but I think all feeling like we wanted to have a sense of direction towards 2019 and that was hard to do when we didn’t have the leadership issue resolved,” he said. email@example.com The Hill Times Ridings where the NDP came second in 2015: Riding First Place Candidate First Place Vote-share Second Place Candidate Second Place Vote-share St. John's East, N.L. Liberal MP Nick Whalen 46.73% NDP incumbent Jack Harris 45.3% Gaspésie—Les Îles-de-la-Madeleine, Que. Liberal MP Diane Lebouthillier 38.73% NDP incumbent Philip Toone 32.5% Chicoutimi—Le Fjord, Que. Liberal MP Denis Lemieux 31.09% NDP incumbent Dany Morin 29.7% Lac-Saint-Jean, Que. Conservative MP Denis Lebel* 32.27% NDP candidate Gisèle Dallaire 28.5% Beauport—Limoilou, Que. Conservative MP Alupa Clarke 30.58% NDP incumbent Raymond Côté 25.5% Québec, Que. Liberal MP Jean-Yves Duclos 28.90% NDP incumbent Annick Papillon 27% Compton—Stanstead, Que. Liberal MP Marie-Claude Bibeau 36.88% NDP incumbent Jean Rousseau 27.4% Saint-Jean, Que. Liberal MP Jean Rioux 33.16% NDP candidate Hans Marotte 29.1% Mirabel, Que. Bloc Québécois MP Simon Marcil 31.49% NDP incumbent Mylène Freeman 30.1% Ottawa Centre, Ont. Liberal MP Catherine McKenna 42.66% NDP incumbent Paul Dewar 38.5% Oshawa, Ont. Conservative MP Colin Carrie 38.17% NDP candidate Mary Fowler 31.9% Davenport, Ont. Liberal MP Julie Dzerowicz 44.26% NDP incumbent Andrew Cash 41.4% Toronto—Danforth, Ont. Liberal MP Julie Dabrusin 42.34% NDP incumbent Craig Scott 40.2% Hamilton East—Stoney Creek, Ont. Liberal MP Bob Bratina 38.99% NDP incumbent Wayne Marston 32.7% Niagara Centre, Ont. Liberal MP Vance Badawey 35.68% NDP incumbent Malcolm Allen 31.5% Sarnia—Lambton, Ont. Conservative MP Marilyn Gladu 38.82% NDP candidate Jason Wayne McMichael 31.1% Kenora, Ont. Liberal MP Bob Nault 35.40% NDP candidate Howard Hampton 33.8% Nickel Belt, Ont. Liberal MP Marc Serré 42.80% NDP incumbent Claude Gravelle 37.8% Saskatoon—University, Sask. Conservative MP Brad Trost 41.53% NDP candidate Claire Card 31.5% Edmonton Griesbach, Alta. Conservative MP Kerry Diotte 40.00% NDP candidate Janis Irwin 34% Kamloops—Thompson—Cariboo, B.C. Conservative MP Cathy McLeod 35.25% NDP candidate Bill Sundhu 30.8% Burnaby North—Seymour, B.C. Liberal MP Terry Beech 36.09% NDP candidate Carol Baird Ellan 29.6% * A byelection is scheduled to take place in Lac-Saint-Jean, Que. on Oct. 23, after Conservative Denis Lebel resigned his seat in June. He had won in 2015 with a less than five per cent vote margin.