Can he ever crack the whip with conviction, given his own reputation as Labour's most disobedient MP?
Whips have been maintaining party discipline and encouraging MPs to vote for the party line since the 18th Century.
The whips' office is a bit like the engine of a car: it generates the power needed to get the vehicle to the places the driver wants it to go.
A notoriously secretive and mysterious bunch, they don't reveal much about their work.
But the BBC managed to talk to some former whips about what it was like trying to keep Mr Corbyn in line when he was at his most disobedient.
"Frankly we didn't spend a lot of time bothering," says Jacqui Smith, who served as Tony Blair's chief whip between 2006 and 2007.
"There were some people for whom it was simply not worth the effort, and he was one of them."
Baroness Armstrong had an eventful time as chief whip between 2001 and 2006. She had to deal with revolts over issues such as foundation hospitals, tuition fees and the Iraq war - Mr Corbyn voted against his party on all three.
Speaking about how the whips' encounters with Mr Corbyn went during these years, she says: "To whip, he was dead easy.
"He was always polite and always told you what he was going to do. But he never wanted to engage in the debate or the argument.
"Politics is about compromise, and he never wanted to be put in a position where he was expected to compromise."
Whips get their name from hunting terminology. The term "whipper in" refers to the rider who cracks the whip to keep straying hounds together in a pack during a chase
The earliest recorded usage of the term in the political context is on 18 November 1742:  Heneage Finch remarked in a letter to Lord Malton that "the Whigs for once in their lives have whipped in better than the Tories".
During 13 years of Labour government - between 1997 and 2010 - Mr Corbyn was the party's most rebellious MP, defying his party's whip 428 times
Last week, he suffered the first Commons rebellion of his leadership as 21 of his MPs refused to vote against the government's new fiscal rules.
Nottingham University's Prof Phil Cowley has interviewed Mr Corbyn on several occasions for his books on backbench rebellions.
He recalls how the new Labour leader once told him that he rebelled on only three issues - war and peace, social and economic policy and matters of liberty.
"I pointed out to him that covered everything government does," says Prof Cowley.
Mr Corbyn's past behaviour looks set to come back to haunt him now he needs the loyalty of Labour MPs.
Backbench MP Mike Gapes, who has represented the Ilford South constituency for Labour since 1992, told the BBC: "Jeremy Corbyn can't expect me to be any more loyal to the Labour Party under his leadership than he was to the leadership of Neil Kinnock, John Smith, Tony Blair, Gordon Brown, Margaret Beckett, Harriet Harman or Ed Miliband."
There could be trouble if the new leader tries to change party policy on issues including Nato, the European Union, defence and military action in Syria, says the MP.
Mr Gapes hasn't caused whips any sleepless nights in the past, but is now clear that he will go his own way when he disagrees with his party leader.
"I'm going to vote according to my conscience and the manifesto and the pledges I gave to my constituents, and if there is a sudden change of approach from my party leadership and I am expected to vote against my views, or the policy on which I have a mandate that I was elected on, then I won't do it."
New Labour MP for Birmingham Yardley, Jess Phillips, says that Mr Corbyn can count on her loyalty "at the moment" but that she will examine issues "on a case-by-case basis".
Mr Corbyn has called for a more honest and democratic approach to politics. As one of Labour's most outspoken MPs, has Ms Phillips found she is easily able to communicate her views to the leader?
"He gives me a lot of opportunities to talk to him and his team," she says.
But for Ms Phillips the jury is still out: "He always listens - whether listening turns to action is yet to be seen."
The Birmingham MP is known for her rows on Twitter with shadow international development secretary and strong supporter of Mr Corbyn, Diane Abbott.
Last week, the Labour whips' office took the unusual step of tweeting the names of MPs who defied the party's position on the government's new fiscal rules - Mr Corbyn's first major discipline problem as leader.
What does Ms Phillips make of this party discipline by social media?
She says Ms Abbott should adopt a more cordial approach if she wants to win people over to Mr Corbyn's cause: "I think that if Diane wants us to get behind Jeremy, so far she's clumsily gone about it the wrong way.
"Her intentions are to command loyalty to Jeremy, but her actions to date do the opposite. She should try love-bombing."
The Labour leadership has signalled that it could offer a "free vote" on issues such as military action in Syria and the renewal of Britain's nuclear weapons programme.
A free vote is where MPs are not instructed to vote a certain way by their party and they are usually reserved for matters of conscience.
Prof Cowley questions the point of having political parties if they do not take stances on fundamental issues.
"A free vote on something like Trident or the war in Syria is effectively her majesty's opposition saying it doesn't have a stance on it," he told the BBC.
"That to me is quite tricky, and a remarkable shift in what parties exist for.
"Parties are supposed to exist as an aggregate of interests and allow voters to say why they like this party, or that party. That's why mass suffrage led to mass disciplined parties. It was seen as important to accountability."
By contrast, philosopher and free will advocate Julian Baggini says it's time for a more honest and direct politics and that the "out of date and unnecessary" whipping system should be scrapped altogether.
"All they [whips] do is reinforce the public perception that MPs are serving their own interests and those of their party - not those of the electorate," he explains.
"It's treating MPs like children who will only co-operate with each other if you force them to."
Mr Baggini argues that there's an opportunity in giving politicians more freedom, in that the party will be seen to be made up of people of independent minds and genuine convictions.
Soon enough Mr Corbyn could be forced to choose between his promise of a new "kinder politics" or resorting to the traditional arm-twisting ways of the whips to ensure his MPs do as they are told.
Habitual rebel turned party leader Jeremy Corbyn has already had a taste of his own medicine, when 21 Labour MPs refused to back him in a Commons vote.