Is there enough diversity of views in the political and public sector leadership?
Are there people in their midst who challenge one another's thinking and the conventional wisdom?
There was an interesting lack of diversity in the answers to this question among panellists at a discussion organised by the Behavioural Sciences Institute of the Singapore Management University which I participated in last week.
We had not discussed beforehand what we would be speaking on.
But when the moderator of the forum, Ambassador-At-Large Tommy Koh asked us what was the one big change Singapore needed to overcome the challenges of this increasingly uncertain and volatile world, having naysayers who speak out topped the list.
Here is a sampling of what they said.
Prof Kishore Mahbubani: "We need to create new formulas, which you can't until you attack every sacred cow. Then you can succeed."
Prof Chan Heng Chee: "We need naysayers in leadership teams who can think the unthinkable."
Prof Koh: "When we appoint people to boards, we can also appoint challengers who are subversive and who have alternative points of view. That's the kind of cultural change we want to see. It makes Singapore stronger, not weaker."
I spoke about the tendency here to value and trust those whose thinking and views conformed to the accepted wisdom.
We didn't know it then, but on the same day the forum was held, the Prime Minister spoke about these same issues in another part of town, at another dialogue.
His remarks were published three days later, and this was how he put it: "I try not to surround myself with yes-sir men. That's important because if all you have are people who say 'three bags full, sir', then soon you start to believe them and that is disastrous.
"You need people who have their own views, whose views you respect, whom you can have a productive disagreement with and work out ideas which you might not have come up with."
Asked what his personal approach was to help him stay open to ideas, he said: "The most important philosophy is not to take yourself or your philosophy too seriously. If you think you have found a formula to succeed, somewhere in there you are going to fail."
That's as strong an endorsement as you can get from the top about the need to have a diversity of views in decision-making.
His message is important because the cultural change which Prof Koh spoke about can happen only if the leadership believes in it, shouts it out loud, and shows by example.
There's hope for Singapore yet.
Why is it that so many people now believe this is important for the country?
I think it is because we all instinctively know that when the future is uncertain and full of surprises, no one has a monopoly on wisdom and it is dangerous to have everyone thinking alike.
In fact, this issue about how leaders can avoid surrounding themselves with yes-men has been recognised as a key problem in the corporate world, and with good reason.
Company bosses, too, find it tempting to work with like-minded colleagues and there are too many subordinates willing to play sheep because they want to be in their superior's good books.
The subject is a well-researched one in management studies because it is so commonplace.
In a piece on this in the American business magazine Forbes, bosses are asked to examine critically the composition and background of the inner circle they work closely with.
The writer, Susan Tardanico, lists various types of personality who can help provide different perspectives to the decision-makers:
•The Contrarian pushes you to think differently by taking opposite views and is always thinking of the worst-case scenario.
•The Everyman is plugged into the lower levels of the organisation, helping you understand how your decisions affect them.
•The Optimist is a best-case scenario person, and provides positive energy during difficult times.
•The Bleeding Heart is the empathetic member of the group, making you aware of how your action affects people.
•The Sage is the strategic thinker and coach, helping you to stay calm in a crisis.
How do leaders ensure they have a mix of these people?
Among other things, look through your list and identify the roles each plays with regard to the different types mentioned above.
Tardanico has this other test: "Reflect on your interactions with these "trusted advisers" over the past 30 days. How many have come to you with uncomfortable news or delicate feedback?"
For Singapore leaders, I would add one more: Be more willing to critically review past actions and policies, to openly admit mistakes, if any, so as to learn from the experience.
I think there is a reluctance to do this here, perhaps because we don't want to be seen to be critical of our predecessors and to cause them to lose face. Here, failure is taboo and not regarded as a prerequisite to success. Instead, too often, whenever public and private sector leaders talk about their organisations, they almost always speak glowingly of their achievements.
It wasn't always like this in Singapore. The earlier leaders were often very critical of the way things were done here, about the inefficiency and low standards, and their frankness was sometimes painful to the ears. But it made Singaporeans more aware of their shortcomings and the need to improve.
As a society, Singapore has swung too quickly from one which was always reminded to pull up its socks to one always reminding itself of how successful it has become.
At the forum, one of the speakers, Singapore Management University president Arnoud De Meyer lamented the reluctance to talk openly about mistakes.
Remember the ambitious plan to develop Singapore into an education hub, attracting students and educators here, he asked.
It was much talked about some years ago, but the project seems to have been quietly dropped without much public discussion or explanation. Was it a failure, and if so, what were the problems?
How can Singapore improve if people are not prepared to talk about past mistakes openly and constructively and learn from them?
If more of them did so, perhaps attitudes towards failure might change, and there will be a greater willingness to take risk, and to speak up. So, here is my addition to the list above:
•The Singaporean who is not afraid to talk about failure.
•The writer is also a senior fellow at the S. Rajaratnam School of International Studies, Nanyang Technological University.