How do you prepare for tough and unexpected questions?

This does not directly answer the question but is an important answer for me. I always watch quality speakers before I give a talk or do a debate or whatever. And by that I usually mean I watch standup comedians who are basically ready for everything and also have a lot of on-stage charisma.

For instance, if presenting an investing strategy, the obvious question is always, "If this is so good, why are you sharing it?" Or if presenting a company to VCs there are a host of obvious questions that I have to prepare for: why hasn't someone done this before? What do you think of the competition? When will you make a profit? etc.

It's important to prepare these with unique answers that they haven't heard a million times before.

It's good to answer these BEFORE they ask them.

This is an important technique, but particularly for debates or arguments. Even arguments with a spouse.

It's very easy when things are heated for people to change the topic.

I was once debating on whether or not people should vote. My side was, "we have a 'right' to vote but we are not forced to vote. This is a free country."

The other side was, "Everyone needs to vote."

One thing the other side said was, "Not voting is equivalent to racism."

And I had to label by saying, "It seems like you are changing the subject. I am happy to debate about racism if you want (I am against all racism) but are we deciding to change the subject on whether or not people should be forced to vote?"

“People died for your right to vote!”

A hollow man is an invisible person I now have to defend myself against.

Say: “I did not realize that if some invisible person (the “hollow man”) died for my right to vote 300 years ago then that means I have to vote.”

Always pointing out the technique brings it back to the debate.

When I wrote my article about NYC having problems, many many people would write me and say, "People are smiling at the outdoor cafes."

This is not relevant in a discussion of is NYC is safe. Again, say, "that's a great anecdote but let's look at data." And, of course, be prepared with data (60,000 stores and restaurants shut down in NYC during the pandemic lockdowns).

If the debate is in front of an audience, say, “We are all interested in this question for the same reason: we would like to reduce crime / be smarter / make a better society / etc.

This is useful in comedy: “You’re from Canada? Me too! What street?”

Useful in selling a company: “This partnership can help us all bring down [competitor].”

Agree with all good points made by the other side.

Express their arguments even better than they did. But then question the assumption.

“Cynicism is bad. People should be engaged.”

Yes, 100%, voter literacy and showing the importance of each issue would certainly get people more engaged and result in a better society.

But are there are better ways, or perhaps different ways, to be engaged than voting?

I need to be able to argue THEIR point better than they can.

Charlie Munger calls this “Invert!”

I had to ask myself before the debate on voting:

What would convince me that forced voting is good?

How can I be convinced it is ethically wrong to not vote? What if one vote made the difference? What if voting would encourage me to be more engaged, more part of a community? More familiar with issues? What if there is evidence that more voting makes life better? What if it’s true I can do two things. Make impact AND vote.

Be able to teach them how to argue with you. Or teach them even better questions to ask you. Like, "I agree it's important to know when we will be profitable. We can be profitable day one but if we use some of our profits for XYZ R&D then our profits will be even great year two because of.."

Compliment your questioner(s) with the attributes you want them to have. This is shaping.

“The audience is here because they feel it’s important to work for a better, more fair system.” or “The moderator is asking balanced questions and staying on point”. Or “I’m glad my opponent and I are open-minded enough to consider that the other side might be correct.”

Shaping triggers a cognitive bias to act in the way shaped. Nobody wants to disappoint.

Comedy use: “Thank god lockdown is over. I can tell you guys are out to have a good time.”

Selling a company: “I want to work with you, most importantly, because I only work with honest people.”

If someone is asking me about cryptocurrencies and says, "Crypto shouldn't be around because criminals use crypto for private transactions."

They are using a weaker subgroup of cryptocurrencies and conflating them to the entire group.

Point this out: "criminal transactions are less than 1% of crypto transactions" (data) but also label this: "this is a straw man question. The average crypto user is not a criminal."