The setting up of the Municipal Services Office (MSO) to improve inter-government agency cooperation in municipal issues embarrassed Nanyang Business School dean Neo Boon Siong.
Its formation in 2014 was the "clearest sign of how our agencies cannot work together to solve simple municipal problems", he said.
Professor Neo, who is also a fellow at the Civil Service College, pointed out in a speech that Singapore's past success may hamper its ability to deal with the challenges of a fast-changing world.
He said public and private organisations have developed blind spots on what can or cannot be challenged, and this has the unintentional consequence of diminishing their capacity to deal with uncertainty and disruption.
"I think we are losing our capacity to think ahead... We have a long way to go in developing our ability to think across boundaries and to innovate," Prof Neo said at a conference organised by the Singapore Management University's Behavioural Sciences Institute with the theme "Unintended consequences in Singapore''.
He and other speakers at the conference gave their views on how Singapore will deal with uncertainty in a range of areas, from the impact of the country's adoption of technology in its push to become a smart nation to how the private and public sectors respond to change.
The MSO, Prof Neo noted, was the outcome of the "silo system" of statutory boards - each with its own clear focus and mission - that Singapore has created.
The country's approach of setting up statutory boards has achieved tremendous results in the past, he said, highlighting how the Housing Board and Economic Development Board created housing and jobs in the early years.
It has set up a number of such boards in recent years, he noted.
But as problems become more complex, they may no longer fall neatly into the functional role a typical statutory board may have.
What might have worked in the past may not always be the best way forward, added Prof Neo.
Singapore must, in its public and private sectors, look not just at efficiency but also at innovation, he said, citing the Monetary Authority of Singapore's approach towards financial technology as an example.
It has created a "regulatory sandbox", which provides a safe space where Singapore's banks can experiment with and test new technology, without potentially affecting their main operations or customers, even if the project fails.
This is a different approach from the regulation he has seen in many parts of the Government, he said.
"I think it's acceptance and acknowledgement that pathways forward cannot be based on past experience, and no matter how experienced (the Government) is, it's not going to be adequate because we're charting paths that we've not taken before, and are relatively unknown," he added.