Open this photo in gallery NDP Leader Jagmeet Singh uses an umbrella to shield himself from the rain as he visits the Rumble on Gray Street Fair, in Burnaby, B.C., on Sept. 15, 2018. DARRYL DYCK

Jagmeet Singh has recently been sitting through sessions with experts in key areas of federal policy. The sessions are aimed at making him more authoritative on subjects the national leader of a left-of-centre party should be authoritative about.

New Democrats had best hope that the erstwhile provincial politician is exiting the policy “boot camp,” as one participant described it, in vastly improved shape – able to compellingly make the case for a national pharmacare program and other affordability measures likely to be central to the NDP’s platform, and confidently beat back concerns about his competence.

As next year’s election draws near, they don’t just need Mr. Singh to be decent. They need him to be enough of a force to reverse the NDP’s precipitous organizational decline, and save it from the electoral disaster that was in the making even before he took its helm.

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The direness of the NDP’s situation is partly evident in publicly disclosed fundraising numbers, which show it trailing distantly behind the other two major parties and not positioned to finance a robust national campaign in 2019, as its poll numbers sit in the teens.

Conversations with party insiders shed further light on how badly its infrastructure eroded in recent years – a result of what veteran MP Nathan Cullen called “a mix of circumstantial and self-inflicted problems” – along with some sense that Mr. Singh has belatedly come to terms with the mess he inherited.

The erosion began right after the party’s 2011 surge to Official Opposition, when Jack Layton died and was replaced by Thomas Mulcair, who was well-regarded in Ottawa but ill-suited to maintaining a strong national organization. But the period leading up to the 2015 election – when the NDP’s proximity to government helped draw in many of its best organizers and strategists – looks like the glory days when compared to what came after it fell back to being the third party.

Whether or not the NDP was right to dump Mr. Mulcair in its 2016 leadership review, it blundered horribly by waiting a year and a half to choose his replacement, and letting Mr. Mulcair stay on in the meanwhile. An interim leader might have maintained a decent energy level; Mr. Mulcair apparently checked out.

By multiple accounts, the NDP wasn’t even calling through its existing donor list to avoid backers dropping off or payments lost to expired credit cards. And there are plenty of similar stories of political malpractice in matters such as digital outreach and volunteer engagement.

By the time Mr. Singh took over, there wasn’t a moment to spare before kicking election preparations into gear. But he proceeded to squander about eight months, apparently convinced his momentum from the leadership campaign would carry over. Fundraising, candidate recruitment, training, research and policy development kept languishing.

Mr. Singh’s inexperience layered on additional problems. He tried to make a virtue out of not having a seat in Parliament and being free to spend time in places other than Ottawa, surrounding himself with fresh faces from outside the NDP’s backroom culture. He did little to build relationships with party grandees. His reward was party disunity as he made ill-advised efforts to assert himself, such as his attempt to discipline veteran MP David Christopherson for breaking ranks on a parliamentary vote.

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In fairness, Mr. Singh was not the first rookie leader to take time to realize that leading a party requires a different skill set than seeking to lead it. He also took time to reach outside his circle for help – that started happening around June.

Veterans of the party’s senior ranks seem cheered by the recent appointment of Marie Della Mattia, who has built a reputation as one of the NDP’s top operatives while working primarily at the provincial level as national campaign co-chair. There is also a new communications director, and a return of digital and fundraising pros who were around before 2015. The message when the NDP caucus convened earlier this month was that after a summer of such outreach, campaign preparations are now ramping up.

But national organizations normally aren’t built in a year. After Mr. Layton painstakingly professionalized his party, the NDP is now almost starting again from scratch.

What New Democrats are telling themselves is that we live in an era in which elections can swing very suddenly – and there’s no way of knowing, with most Canadians yet to have much exposure to Mr. Singh, whether he will strike an appealing contrast to other options.

That puts a lot on the shoulders of a raw politician in the midst of his own "reset,” alongside the organizational one.

The plan his strategists seem to be gravitating toward involves a sort of left-wing populism that taps into frustrations around opportunity and affordability in rust belts and urban cores and especially suburbs, where he is supposed to hold strong appeal. He also seems to be rallying the left by getting more assertive on articles of faith, including pipeline opposition.

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What Mr. Singh showed in the early days of his leadership – tentativeness on core-policy matters, platitudes in place of detailed positions, glibness more than common touch – suggests it won’t be easy for him to lay the groundwork in the available time. Never mind having to spend much of his time in B.C. campaigning in a by-election he can’t afford to lose.

But one of Mr. Singh’s pitches when seeking the job was that he’s a quick study. He’s being put to that test now, with his party having little to fall back on if he doesn’t meet it.