How to Answer Any Question—Even the Tough Ones
3 tactics to answer any tough question with confidence
In 2007, 18-year-old Caitlin Upton, Miss South Carolina at the Miss Teen USA Pageant, got a tough question:
"Recent polls have shown a fifth of Americans can’t locate the US on a map. Why do you think this is?"
Two seconds after hearing the question, Caitlin answered:
“I personally believe that U.S. Americans are unable to do so because some people out there in our nation don’t have maps, and I believe that our education such as in South Africa, and the Iraq and everywhere like such as...”
Her answer continued for a few more meandering seconds. Clearly, she was stumped.
Unfortunately for Caitlin, her 48-second struggle to answer became a viral moment.
As uncomfortable as it is to watch, she did what most of us do when faced with a question we don’t know the answer to—we start talking, hoping that somewhere along the way, we’ll land on a good answer.
How would you have answered this question on national television? Imagine being 18 and trying to think on your feet.
Tough questions come up all the time—whether in an important meeting, during a Q&A session, in a high-stakes presentation, or on a customer call.
So what do you do when faced with a tough question?
How do you avoid 48 seconds of word salad and instead deliver a clear, crisp, and competent answer?
The key to handling unscripted answers is structure and time constraints. Have one without the other, and you’re bound to ramble. But with both in place, you’ll stay focused and in control.
First, time constraints—keep your answer between 60 and 90 seconds. Period. (We’ll cover how to do this later.)
Second, structure—a simple framework to organize your thoughts. Here are three go-to strategies for handling unscripted questions:
Two Points
Story + Insight
Thinking Then & Now
Two Points
To create a clear answer, present two points.
Listen intently to the question.
Pause for two to four seconds to gather your thoughts. This pause might feel long, but it does two things:
It gives you time to think.
It shows you’re considering the question carefully.
Next, set up your response with: “You know, that’s a really good question. I think it comes down to two things.”
Then, start with your first point: “The first thing that comes to mind is…” and talk about it.
Follow up with: “The second point is…” and discuss that.
To wrap up, restate your points concisely: “So to answer your question, it really comes down to these two things: [point one] and [point two].”
The key to this tactic is providing structure while giving listeners clear signposts. When you say, “It comes down to two things,” you set expectations, making your answer sound more authoritative—even if it’s not perfectly polished.
You don’t always have to stick to a basic Point One then Point Two approach. You can also use contrast, such as past versus present:
"That’s a great question. I think we need to look at it from both the past and the present. In the past, we saw this issue play out like this…[give some details]. But currently, here’s how things are different…"
Framing your answer this way adds depth and makes your response more engaging.
Story + Insight
The Story + Insight strategy is a powerful tool if you want to connect emotionally.
When you get a question, pause briefly, then set up your response with:
“You know, that’s an important question. It reminds me of …”
Then, tell a short, relevant story—something from your work or a personal anecdote that ties into the question.
The key is to keep the story tight: a clear beginning, middle, and end. Jump straight into the action and avoid over-explaining.
Once you’ve shared the story, don’t assume your audience will automatically get the lesson—spell it out. Wrap up with a concise takeaway:
“That experience taught me that…”
Ideally, you should have a few go-to stories for different situations. Since people remember stories better than abstract facts, this method makes your answer more engaging and memorable.
Keep it under two minutes for maximum impact—ideally 60 to 90 seconds.
Thinking Then & Now
Sometimes, you’ll get a question based on incorrect or outdated information. It is best to avoid saying, “That’s wrong.” That approach rarely works, and get defensive or people shut down.
Instead, use the Thinking Then & Now method. This approach helps your audience to see why their view once made sense while you guide them toward a new understanding.
Here’s how it works:
Get the question, pause, and say: “I used to think that, too. It made a lot of sense because . . .”
Then pivot: “But after looking into it, I found that...” Introduce the new information and explain why your thinking changed.
If you never held that belief yourself, you can adjust make your appeal more generic, like this:
“A lot of people think that, and it does feel true at first. So I looked into it, and here’s what I found…”
The key is to avoid directly telling the questioner they’re wrong. Instead, guide them through a thought process that helps them avoid being wrong in the future.
One important note: This technique is about persuading, not manipulating. Don’t pretend you’ve changed your mind if you haven’t.
Practicing for Better Answers
In addition to selecting the correct structure, you need to limit your answer with a time constraint. Allow yourself 60 to 90 seconds to deliver your structured answer. Then drop the mic.
Structure and time constraints. Now, all you need is some practice.
A great way to practice is by setting a 90-second timer and answering tough questions using these methods.
Try this:
Identify two or three questions you find difficult to answer.
Set a timer for 90 seconds and answer one using the Two Points method. It might feel clunky at first but try it again.
Next, answer the same question using the Story + Insight approach. Does a relevant story come to mind?
Finally, take a question where people often have incorrect information and apply the Thinking Then & Now framework.
Spend 10 minutes a day for five days answering 2–5 questions using these techniques. By the end of the week, you’ll have the confidence and structure to handle any unscripted question that comes your way.
Bonus: How Caitlin Could Have Answer the Question
If Caitlin had used these techniques, here’s how she might have responded:
Two Points
“Thank you for that question. I believe it comes down to two things. First, education is struggling. Many students in South Carolina and across the country are below grade level in reading and other subjects, so it’s not surprising that geography is also a challenge.
Second, our media is heavily U.S.-focused. When young people and adults hear the news, it’s almost always about America. In other countries, news coverage includes more global perspectives. So when we combine struggling schools with a media that rarely discusses the rest of the world, it’s understandable that some people might not be as familiar with geography.”
Story + Insight
“Thank you for that question. This reminds me of my third-grade teacher, Mrs. Turner. She made us memorize every country on the globe. At the time, I thought it was pointless. But later, I realized how valuable it was—it changed how I see the world. Now, when I hear about a country in the news, I know exactly where it is.
If one-fifth of Americans struggle with geography, maybe they didn’t have a ‘Mrs. Turner’ in their life. That’s something we should work on—making sure every student has the opportunity to learn about the world in a way that sticks with them.”
Thinking Then & Now
“You know, I’ve heard statistics like this before—claims that 20% of Americans don’t know this or that. But here’s what I’ve learned: a lot of these numbers come from small sample sizes, online surveys, or data that’s been massaged to create a clickbait headline.
What I do know, from talking to people in South Carolina and from the amazing contestants I’ve met here, is that America is full of bright, curious people from all backgrounds. I don’t believe one in five Americans couldn’t find our country on a map. That statistic might make for a good headline, but it doesn’t reflect the people I’ve met and the country I know.”