How to Have an Insightful Conversation

Everyone wants to come across as wise in every conversation. However, only a few are naturally endowed with this ability. With some simple tips and a commitment to practice, anyone can become a more skilled conversationalist.

Focus on having an effective conversation before aiming for wisdom in one. Before becoming wise, you need to improve your "communication awareness." No matter how wise you are, diving too deeply into a conversation with a humorous story or a teasing remark can make you seem over the top. Practice the "Observe-Ask-Answer" technique used by diplomats.

• Start the conversation by clearly showing that you are genuinely interested in it. In social situations, it is most important to appear approachable through non-verbal cues, such as open body language and a smile.
• Develop the conversation by sharing casual stories wisely. Every conversation needs a starting topic. Begin with harmless questions or comments about what’s happening around you to move the conversation forward. Are you outside? How’s the weather? At a party? What kind of food is being served?
• If you're talking to a stranger, transition from casual chatter to introductions and let the conversation naturally evolve from there.

Ask Questions. To understand what makes the person you're speaking with engaged, you need to learn more about them.

• Most people enjoy talking about themselves, so give them a chance to share. Avoid yes/no questions. Instead, ask open-ended ones. For example, when someone talks to you about their career, ask them what they love most about it. When in doubt, ask "Why?"
• Let the other person know you're genuinely interested in what they're saying by maintaining eye contact and using interjections like "Really?", "Is that so?", and "Uh-huh". Avoid interrupting, even if you have something to say.

Be Present. Often, when you're trying too hard to appear wise, you become distracted while listening because you're too focused on what your next comment should be. However, to be truly wise, you need to focus entirely on what the other person is saying. Listen attentively to their words.

• Don't interrupt. Even if something the other person says sparks an idea in your mind, wait for a natural pause in the conversation to respond. While your comments might be valuable, interrupting will come off as impolite.
• Pay attention to the flow of the conversation. Whether someone sounds wise or not depends on timing. Listen carefully to understand when it's your turn to speak. If you miss the right moment, your responses won't have the same impact.

Find Common Ground. Once you know more about the person you're speaking with, you can begin to identify shared interests and find topics that could make for a great conversation.

• Think about experiences you've had that are related to their interests. When the time is right, bring that experience into the conversation.
• Sometimes, all a conversation needs is one shared experience. For example, if the person you're talking to loves fishing but you've only been fishing once, reflect on the mistakes you made and share them—it could be an amusing or relatable anecdote for them.
• Know your audience. British author Somerset Maugham once said, “quotations...are a substitute for witnessing.” In truth, references to culture—whether books, movies, TV shows, politics, etc.—can shortcut the need for direct experience. However, for those references to be effective, you need to know who your audience is.
• For example, if you're talking to someone from the Baby Boomer generation, quoting a song by Trịnh Công Sơn will likely resonate more than quoting a song by Mỹ Tâm.

Learn Some Small Talk. Everyone enjoys a good laugh. But it’s hard to get people to laugh with a vague or confusing story. Instead, you should have a few lively, clear stories prepared to share at parties or social events.

• Think about funny or bizarre stories from your own life. These should be stories that help move the conversation along.
• Consider who your audience is. If your goal is to sound wise in a conversation about accounting, accounting-related stories will be appropriate. However, if you're looking for funny stories to tell anywhere, those about shared experiences—like school, parents, pets, or children—are the best, since many people will have similar experiences.

Making Them Humorous. The same story can be confusing, boring, or even humorous depending on how you tell it. To make sure your story gets the laughs, you need to polish it.

• To find what makes your story funny, look for humorous phrases and exaggerated expressions like those used by comedians such as Xuân Bắc.
• Create an outline for your story. Try to recall the details, and review whether your story is engaging, clear, and humorous. Pay attention to your tone of voice when you tell it—your delivery should be just as funny as the text on paper.

Subtle Jokes. If there are others in the conversation, try making playful remarks about them naturally.

• Make jokes about celebrities, singers, or politicians, but make sure the listeners aren’t fans of those individuals.
• Don’t go overboard. Avoid jokes about someone’s appearance, family background, gender, or disabilities unless you know they are open to such humor. Even if they joke about their own flaws, they may not want to hear it from someone else.

Wordplay. Certain elements in a conversation can be funnier through clever wordplay. Even if you’re not an expert at it, you can still improve with practice.

• Enhance your vocabulary. Wordplay heavily relies on a rich vocabulary. Look for books to expand your word knowledge, explore apps, or try word games like crosswords to boost your command of language.
• Understand the types of wordplay you use. Word twisting (like saying 'Sáng ăn khoai' instead of 'Khoái ăn sang'), mispronunciations ('nhảy điệu flamingo' instead of 'nhảy điệu flamenco'), slang ('Con ngựa đá con ngựa đá'), and portmanteau words ('Chrismukkah,' combining 'Christmas' and 'Hanukkah') can add wit to a conversation if used skillfully.
• Learn from examples of great wordplay. Great literary figures like Nguyễn Du, as well as performers like Xuân Bắc or Sơn Tùng M-TP, have used wordplay effectively in their works and performances. Always keep your audience in mind and study examples of clever wordplay to understand how to use them in your own speech.

Relax and Be Yourself. People often feel the need to act wise because they believe they’re not good at socializing. But insecurity is the enemy of humor.

• Your delivery is what separates a witty comment from a dull one. If you appear tense or shy, your remark won’t come across as funny.
• Remember that your self-perception is usually inaccurate. You may not be as awkward as you think. When you allow yourself to feel insecure, you’re actually hindering your ability to be humorous.

Build Confidence Through Practice. There’s a paradox: the way to overcome a lack of confidence in a conversation is by simply having more conversations!

• The trick is to participate in low-stakes chats (such as casual conversations with the barista while waiting for your coffee) as much as possible. The more you practice, the more prepared you’ll be when it’s time for important conversations (like talking to a colleague you want to approach) and you’ll sound wiser for it.

If Necessary, (Temporarily) Practice Online. If face-to-face communication makes you anxious, try practicing your storytelling, wordplay, and other humorous skills on social media.

• Give yourself the opportunity to invest in your own wisdom. With more time to think through your responses, you’ll build confidence and become more comfortable interacting with others in person.

Stop When You’ve Truly Made Progress. Once you’ve built confidence, you can continue to develop your humor, but at this point, you don’t need to force wisdom into every comment. You’ll know when it’s time to stop trying to be clever.

• The great Shakespeare once said, “Brevity is the soul of wit.” When you feel you’re wise enough, you’ll stop feeling the need to make every comment a witty one. Striving too hard for wisdom at that point can actually become a barrier, annoying or frustrating others.
• Likewise, as you grow more confident in your wisdom, you’ll learn when to wrap things up. The best way is to end the conversation on a positive note, leaving a lasting impression.