Many will hail the decision to make V. Sundramoorthy the first local national football coach in 16 years as a step in the right direction.
But if the former Singapore international striker is offered a one-year deal as the Lions' caretaker, as has been widely reported, the man hailed as "The Dazzler" faces an uphill task to get things right on the pitch immediately.
The new coach is not helped by the fact that his reign will cover two important competitions - the year-ending Asean Football Federation (AFF) Suzuki Cup, as well as the 2019 Asian Cup third qualifying round, which starts next March.
Former internationals Seak Poh Leong and Aleksandar Duric said first on Sundram's list is picking a balanced and competitive squad, one based entirely on merit.
Seak, who coached the Lions between 1987 and 1988, said: "He knows many national players from his days with the Young Lions and LionsXII so I'm sure he already has a core group in mind.
"But for a tournament like the AFF Cup, he needs a good squad of about 22 players and he needs to pick them based on current form, and not for development purposes.
"It's all about getting results."
A complaint against previous national coach Bernd Stange was his preference for youth, sometimes at the expense of experience.
While this meant grooming more youngsters for the future, it resulted in a lack of veterans to guide the rookies.
The national team were found wanting in key moments, such as the final group game against Malaysia at the 2014 AFF Cup, which the Lions lost 3-1 at the National Stadium.
The absence of tactically-disciplined defensive midfielders Fahrudin Mustafic and Isa Halim was seen as a key reason for the Lions' group stage exit.
Duric said Sundram should ace this department, as he coached many of the current national players in the Young Lions and later, the LionsXII.
Another consideration is the use of naturalised players, an issue Stange flip-flopped on.
Initially, the German insisted on picking only local players but he later pushed for the naturalisation of Jordan Webb (Canada), Sirina Camara (France) and Song Ui Young (South Korea).
Webb and Camara have met Fifa's five-year residency rule, while Song will be eligible for naturalisation at the end of this year.
Duric, who applied for citizenship on his own accord and got it on his third attempt in 2007, said it is vital for Sundram, the Football Association of Singapore, and the relevant authorities to come to an agreement on this matter. That will allow the coach to have a better idea of the players at his disposal.
Sundram also needs to determine how big a role Shahril Ishak will play. Stange once said that the national captain, who plays for Johor Darul Takzim II in the second-tier Malaysian Premier League, could no longer cope with the demands of international football.
Stange's lack of trust in the 32-year-old attacking midfielder, appointed captain by Raddy Avramovic in 2010, was evident as Shahril played only 125 minutes in Singapore's eight 2018 World Cup qualifiers.
Hariss Harun wore the armband in Shahril's absence, begging the question: Should a new national captain be appointed to be the coach's lieutenant on the pitch?
Seak, a former national captain said: "It all depends on what role Sundram has in mind for Shahril.
"If he is not going to be a key player then Sundram should reconsider. It's important for the captain to be on the field."
While these issues will weigh heavily on Sundram's mind, there are also selection headaches he will be pleased to have, including who to guard the Lions' goal.
Both Hassan Sunny and Izwan Mahbud have been excellent in recent years, with the former named by British newspaper The Telegraph as the 18th best goalkeeper in the world last month.
Seak said: "The pressure is definitely there but hopefully he (Sundram) gets the same support as his predecessors to do the job for Singapore."
