Hey, if you haven’t already signed up, don’t miss the free ebook at the bottom of this post: 99 Questions for Global Friends.  

I love sitting down with people who have different lenses than I do.

I’m fascinated by the reality that we can look at the exact same thing and see something completely different.

The color red.

The number eight.

A toilet.

When it comes to understanding a different perspective there is NOTHING like the extraordinary power of questions. Not deep, scholastic, perfect questions — but simple ones that open up a whole new world.

If you are blessed enough to have cross-cultural relationships . . .


Here are ten tips for asking great questions that will take you deeper and give you more cultural understanding.



You’ve seen it over and over right? We kick off our our cultural research when it all hits the fan. When there is obvious tension and painful conflict someone in the mix recognizes, “hey, this could be cultural, let’s Google it.”

Too little, too late.

Questions (and answers) are so much better when no one is trying to win.

To be fair, simple questions don’t stop riots. They don’t fix racism. They don’t end wars, but asked in the right way and early enough they set a trajectory that leads to a different place where those things can be avoided.



This is going to sting just a little . . . “You don’t know everything.”

Take a minute . . . continue when you’re ready.

Your understanding of any person or group of people has parameters. Expanding those parameters generally means discovering that there is more to it than you originally thought. In other words  . . . you were wrong (or at least not completely right).

Did you catch that? Being wrong is actually an indicator that you are understanding more (which should be a good thing) BUT STILL, no one wants to be wrong.

If you can celebrate being wrong and create a culture around that you’ll be paving the way for people to go DEEP.



Can we skip through the awkward denial bit here? You have stereotypes. You just do.

They may be more informed and sensitive than others but you sum people up the second you look at them. Your expertise is based on all the information you’ve gleaned to that point.

What if you stopped fighting that, embraced it and then expanded it?

If you’re stereotype is, “Asians are bad drivers” just try expanding that statement a bit . . .

“I’ve always thought that — Asians are bad drivers — but there is probably more to it.”

That’s a COMPLETELY different thought. The first one shuts the door and the second one opens it. The first one convinces you that you already know, the second sets you up to learn.

The first one will see one bad driver, miss fifty good ones and say “see, I was right.” The second will see one good driver and say, “yep, I was wrong.”

Don’t ignore your stereotypes. Don’t pretend they DON’T exist just because they shouldn’t.

Expand them.



If you were Australian (and if you are please back me up here) which of these do you think you would rather hear from someone who is not?

(big cheesy smile and a slap on the back) “Ahh you’re from Down Under . . . (switching to a bad accent) G’day mate, let’s throw another shrimp on the barbie and then go on a walkabout through the Outback with some kangaroos . . . and koala bears.”


“You’re from Australia? I’m embarrassed to admit it but I know basically nothing except what I learned from The Crocodile Hunter. I would love to expand my understanding though.”

That first guy knows something . . . but he exhausted all of it in one sentence. He’s done.  The second guy is ready to get started.

There is no shame in ignorance . . . unless you think you’re not.



It’s usually less painful to tell you what someone else thinks of you than what I think — especially if I think you’re an idiot. Instead of asking directly for a personal opinion, try asking what THEY think someone else’s opinion might be.

So instead of “What do you think of my country?”, ask “What do you think your parents generation thinks of my country?”

This has at least three advantages:

  1. It takes the pressure of offending you off of your friend.
  2. It gives you the potential of more than one answer (see number six).
  3. It gives your friend an indirect way to share his/her own thoughts (more significant in some cultures than others).

Mix it up. Ask the same question from multiple perspectives?



Cardinal sin #1 in cultural understanding is saying “Ahhh, now I get it.”

Unfortunately we generally arrive at that spot after talking to one person. That’s how questions and answers work right? We ask, they answer, problem solved.”

Repeat after me — “There is ALWAYS more to it.”


No matter how strong your sources are there is always a different perspective. Even if one answer is right and five others are wrong you will understand the whole picture more by hearing them all.

Ask different people.

Ask one person about different people.

Ask locals and expats. Ask idiots and experts.

Ask Wikipedia but don’t think you’ve got it regardless of your source.



There is a psychological phenomenon called “Confirmation Bias”.  It basically states that humans tend to embrace information that supports what we already believe to be true.

Click here to read “Why Facts Don’t Change Our Minds” from the New Yorker

It is the loudest voice in politics, religion and law. We not only love being right, sometimes we can’t hear otherwise. That’s dangerous when your goal is to learn something.

When you think you know something about a culture you may find yourself intuitively perched, waiting for verification of your rightness.

If you come away from a cross-cultural conversation simply affirmed in what you already knew . . . you probably missed something.



“Why do Brazilians love football so much?”

Fair question right? You’re even being savvy by not calling it “soccer”.

Here’s the problem. This question puts all of the pressure on ONE person to give a definitive answer on behalf of 200 million others. They need to package the history and the passion and the politics of the entire question so you can carry it home with you.

Here’s the other problem. They will. And you will walk away with your answer — not needing to ask anyone else.

Maybe consider asking from a different angle.

“What’s your football story?”

“Did you play when you were young?”

“How did people in your home feel about it?”

“In your neighborhood?”

“What’s it like when the world cup rolls around?”

You won’t get your definitive answer, but by the end of this conversation you will know something about football in Brazil . . . and families . . . and neighborhoods . . . and passion . . . and politics . . . and history . . . and so much more about your friend.

Stories beat answers every time.



This is tricky because boundaries aren’t always clear and they change with relationship. A typical cross-cultural faux pas is to presume a deeper relationship based on misread cues.

A smile that means, “we’re best friends” where you come from may just mean, “I’m uncomfortable” for them.

The best way to respect boundaries is to keep it simple, especially in the beginning. Let the relationship grow and the boundaries will move. Eventually you’ll have a friend that you can ask anything without offense.

THAT is cross-cultural GOLD.



We all do this —  They’re telling a story . . . it triggers a thought . . . AS they are talking we start forming our own story in our heads just waiting for a pause to pounce on.

If you are normal it is difficult NOT to reroute conversations.  It’s also NOT a bad thing to have a story.

Timing matters though. Develop the discipline of forming questions before you form responses. Don’t check out because you thought of a better story. Hear the whole story and dig some more.

Try going FIVE DEEP . . . proactively determine at the BEGINNING of the conversation that you will ask 5 questions before you add your story to the mix.

Know going in that 5 is not a magic number. Ask 20 if it feels right and don’t ignore them if they ask you a question after you’ve only asked 2. However, changing your posture on the front end will take you to places you won’t get to otherwise.


Were only scratching the surface here.

The art of asking questions, though, is more about doing it than learning how.

Sign up in the blue box below to get a free ebook: 99 Questions for Global Friends.

Pick a number from 1 to 99 and start asking.

I’d love to hear your story.



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