It was late on a Saturday and the group was still far from a consensus. And as the time ticked ever closer to the point of no return, the pressure started to fray some nerves.
"We've got maybe five minutes left and we still don't have a decision. If we don't figure this out soon, we might have to call the whole thing off," said one person in a huff, reminding everyone present about just how much was at stake.
The big stumbling block was two naysayers. And no matter what anyone did, no matter how reasonable the justification, both stubbornly refused to budge.
"Nope, no way, absolutely not," said the main naysayer. "If you all want to watch Lego Batman, we are just going to go home. I don't understand why nobody wants to watch La La Land."
In the end, La La Land did not win, but neither did Lego Batman. The argument had dragged on past the start times for both movies.
I was reminded of that recent episode of naysaying last week when two different dialogues included reminders of the need for Singapore to have more naysayers.
One panel of academics and former senior civil servants lamented the way many civil servants seem reluctant to put forward contrarian views to their bosses.
As Singapore Management University behavioural scientist David Chan jokingly noted during the discussion: "You talk so much to me but when the minister is present, in front of him, you're absolutely silent."
Prime Minister Lee Hsien Loong made a very similar point at a dialogue on the same day as he stressed the importance for leaders to steer clear of yes-men.
"If all you have are people who say 'three bags full, sir', then soon you start to believe them and that is disastrous," he said.
I say a big yes to that.
I completely agree that we do need more people to have the courage to provide contrarian views.
(Review question: If a leader calls for there to be more naysayers and you refuse to challenge it - does this act of rebellion make you a naysayer even though all you've said is yes? Discuss.
Bonus question: If that act of rebellion does, in fact, make you a naysayer, does this mean you have complied with the call and are then, therefore, no longer a naysayer?)
Now, calling for naysaying is one thing.
Getting it to actually happen is a different thing altogether.
Because let's be frank about it, naysaying is never consequence-free. There is always a price. The person who disagrees is generally looked on unfavourably by his peers and superiors.
Many a married man who has tried saying no to his wife can attest to how heavy the price of naysaying is.
In efficiency-driven Singapore, a naysayer can also be a real drag on proceedings.
After all, if not for naysayers, Lego Batman would have happened for me by now. And thus even though I am personally supportive of more naysaying, I can't say I was thrilled with the two La La Land enthusiasts.
You see, for many who can agree intellectually that it is important to have people willing to challenge set ideas, it is still difficult to put that in practice when it is your set idea that is being challenged.
Naysaying is sort of like a root canal. You understand its necessity in the abstract but you would much rather it happen to someone else.
To make matters worse, the Internet is teaching a whole generation of young people that they never have to encounter an opinion they disagree with. Disagree with something online? Just block it.
It's so much easier than getting into a flame war.
So what can we do about it?
I've come up with three proposals.
1. NAYSAYING COMMITTEE
We've used this particular method to solve some of our most intractable problems, so there is no reason to believe it won't work here.
All organisations need to do is to set up little committees full of people whose entire job is to be naysayers. They'll actually be punished if they agree with a suggestion.
That way, a lot of people can be completely compliant with their bosses' wishes while actively naysaying.
Of course, just like every other committee, we need to guard against groupthink even within the naysaying committee.
So we will likely need naysaying sub-committees and naysaying sub-sub-committees to make sure everyone is properly challenged. (I am prepared to accept some groupthink at the naysaying sub-sub-committee level.)
If that sounds too manpower-intensive, we can try:
2. MASS SURVEILLANCE
As Professor Chan noted during the discussion, naysaying is already quite rampant.
The only problem is that the decision-makers are not around to hear it when it is happening.
Operating on the assumption that most governments are already spying on their citizens the same way the US National Security Agency does, it means we may already have hard drives full of naysaying lying around somewhere.
We just need to formalise a procedure that gives bosses access to them.
Maybe all of it can be put into a searchable database so that people can just input their name and it will pull out recordings of their subordinates' naysaying.
3. NAYSAYING HEROES
A good way to help people come around to the idea of challenging authority is to show them examples of people who have done it and then gone on to lead successful, productive lives.
We should find these people and share their stories.
Perhaps it could be an employee who dared stand up to his boss and is now running the company, or maybe a rebellious soldier who is now commanding a platoon.
Or maybe it could be a vigilante who constantly challenges conventional notions of law enforcement but still ends up saving the city - a naysaying hero dressed up like a bat and made of Lego.