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Let’s start with the positive news for NDP leader Jagmeet Singh: he still has a job.

His big win Monday night in the Burnaby South by-election will quell, for now, the doubts and speculation about the future of his leadership. Despite insisting that he would have remained in charge even if he’d lost, the reality is he wouldn’t have. The federal caucus of the party would have insisted on change at the top.

He would have been toast.

But he won a contest where the stakes couldn’t have been higher. He is the first racialized leader of a federal political party to take a seat in the House of Commons, so there is also a historic element to this victory which shouldn’t be overlooked.

Still, in many ways, the hard part now begins for Mr. Singh.

NDP leader Jagmeet Singh celebrates his by-election win in Burnaby, B.C., on Feb. 25, 2019.Jonathan Hayward/The Canadian Press

He has so many priorities it’s hard to know where to begin. But the first is likely altering the narrative that has developed around him since becoming leader in October, 2017. And part of that narrative is that he is often poorly informed and ill-prepared.

He won’t be able to turn to aides and ask what the party’s policy is on a particular issue, as he once did, to the embarrassment of NDP MPs. He will need to be thoroughly briefed on major national and international developments. There will be no excuse, for instance, for being unaware that China’s ambassador said “white supremacy” was a factor in Canada’s detention of Huawei chief financial officer Meng Wanzhou, as happened when Mr. Singh was asked about the remark on CTV’s Question Period, which was taped a day after the comments made international headlines.

“It wasn’t the first year [as leader] that I think he would have wanted, but now he has a chance to change that,” veteran NDP MP Nathan Cullen told me. “He will need to get better at the type of complicated and hard questions that we face as national politicians.”

Mr. Cullen is one of the people in the NDP caucus Mr. Singh is going to have to rely on in the early going. He will need to maintain the backing of the party’s most influential MPs, if for no other reason than to maintain control of a caucus he does not know like a leader would if they already had a seat in the House of Commons. He will need to cultivate a relationship with this group or risk the internal back-stabbing and sniping for which the NDP has sometimes been known.

Mr. Singh will also need to develop a presence in Parliament during Question Period. That is harder than it looks.

It’s not easy to get up in front of 337 fellow parliamentarians and, in a cogent and forceful manner, demand answers from the Prime Minister. It can often take new MPs one election cycle or more to feel comfortable on their feet in the maelstrom of QP. Mr. Singh does not have that luxury; he needs to be good, and noticeable, in a hurry.

Then there is the problem of Quebec. The NDP is in deep trouble in the crucial province – they lost another seat there in Monday’s by-elections, one once held by Mr. Singh’s predecessor, Thomas Mulcair – where disdain in some quarters for religious symbols and clothing make for a difficult fit with a federal leader who wears a turban and kirpan as a practising Sikh.

“I think Jagmeet has to be able to demonstrate how his faith enhances, rather than gets in the way of, his politics,” said Mr. Cullen. “I think he needs to make the distinction between one’s personal faith and public work. It’s an issue not to be ignored. My advice would be to speak right to it.”

Finally, Mr. Singh needs to demonstrate that his party is still an attractive political vehicle for Canadians of a progressive bent. Convincing a group of high-profile Canadians to run for the party in the next election would help immensely. In the last several months all we’ve heard about are NDP MPs deciding not to seek re-election, fueling a developing narrative that people are fleeing a sinking ship.

Mr. Cullen doesn’t underestimate the enormity of the task ahead of Mr. Singh, but nor does he believe that Mr. Singh’s not up to it.

“I think a lot of people have written Jagmeet off far too quickly,” he said. “While it’s been a difficult year, there is nothing but opportunity ahead of him.”