19 Simple, Concrete Tips for Mastering the Art of Conversation with Anyone
Wednesday August 6, 2014

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Cheerfulness, unaffected cheerfulness, a sincere desire to please and be pleased, unchecked by any efforts to shine, are the qualities you must bring with you into society, if you wish to succeed in conversation. … a light and airy equanimity of temper,—that spirit which never rises to boisterousness, and never sinks to immovable dullness; that moves gracefully from “grave to gay, from serious to serene,” and by mere manner gives proof of a feeling heart and generous mind.” —Arthur Martine

The good news about knowing how to navigate any conversational situation you may find yourself is that nobody is born an expert, but rather it is a learned skill that is honed with practice and observation. Often young adults seem to have this innate ability to talk and converse with anyone, but if you were to delve in to their childhood, you would no doubt find an adult/parent/sibling that they either observed or had an opportunity to practice with on a regular basis. Now our personalities may be hard-wired to make some more comfortable with this craft than others, but just knowing that we can all master the art of conversation should ease your mind.

After all, whether for work, building personal relationships or navigating in the world at large – travel, working with people as we do our errands or hire people to work on our homes or negotiate any deal, knowing how to politely, yet effectively converse with people (whether we know them or like them) can greatly effect our mood, stress levels, success and ease as we go about our everyday business. So today, I wanted to share 19 tips or ideas on how to skillfully navigate any conversation.

Let me begin by assuaging any fears, I am not perfect at all of these, but I try diligently to improve or recognize when I could have done better after the conversation has ended. Like anyone else, I have good days and bad days, but simply remembering and trying to integrate each of these when I can has shown the strength of poetic skill of conversation.  Each one really does hold the ability to shift a so-so discussion into something much more enjoyable. Have a look.

1. Be the Bearer of Good News

The best conversations are the ones that leave you inspired and eager to resume the conversation with the people that were involved. While insincerity and lack of acknowledgment to the events that brought you together shouldn’t be ignored, bringing unnecessary sad or negative stories is a quick way to break up the conversation.

2. Refrain from Correcting Your Conversation Partner

Unless you are a parent, a teacher or instructor, the need to correct someone for stating an error (unless they are speaking ill of a good friend who needs to be defended) is unnecessary, and often perceived as rude. Often people misstate benign information, and in such cases, just let it go. Your thoughtfulness will be appreciated when the speaker discovers their error. For example, in a conversation with my mother recently, we were discussing  a pattern she was sewing, and I couldn’t think of the word “pattern” (a brain fart moment – yes), so I inserted the word “recipe”. She knew precisely what I meant and there was no need for correction or teasing. The conversation continued to flow, and I appreciated her understanding.

3. Acknowledge Others’ Points, Opinions or Statements

In any conversation with one or more people, the quickest way to show genuine interest, is to demonstrate you were listening. To do so, simply acknowledge their story, feelings, etc by either remembering them later in the conversation, stating, “As Lori informed us earlier . . . “ or sharing your agreement – “Sophie, I never thought about [insert issue] from that perspective. Thank you for sharing that with us.”

4. Pose a Question to Stimulate Conversation

Based on the interests and expertise of the people you are conversing with, pose questions that you think they would be comfortable asking or would be able to use their knowledge to provide better insight. A few years ago, I was introduced to a federal attorney at a summer gathering, and as a civics teacher I was eager to ask them about a particular Supreme Court ruling that was just issued. Not only did I learn something, but I was able to gain a bit of perspective beyond the classroom.

5. Create moments of inspiration to encourage conversation

Sometimes, asking a question can be tricky if you don’t know the people all that well that you are talking with. In such a case, often it is the topics we discuss or stories we tell that prompt someone else to want to share something, and that is quite a compliment all by itself. Whether it’s sharing something about yourself that grabs their attention, opens their eyes to the unexpected or is a bit of news that perks the conversation up, when in doubt, come with a few great fail-safe inspiring stories (being self-depreciating isn’t a bad idea either).

6. Know When Silence is Best

“Eloquent silence” as coined by Arthur Martine in his 1866 book Martine’s Hand-Book of Etiquette and Guide to True Politeness is knowing when to simply listen which is just as polite as knowing what the appropriate thing to say or how to speak politely. In fact, he reminds, silence, if practiced or timed correctly, is a way of encouraging others to speak. Keep in mind – Speak less. Listen more. And as a practice, paraphrase back what you heard them say to show respect, your attention and to make sure you understood them correctly.

 7. Prefer Selfless to Selfish Conversation

The easiest topic for anyone to talk about, as they are the expert, is themselves; keep this in mind when you don’t know where to take a conversation. Begin by asking them how they know the host, and perhaps another topic will present itself.  After all, as Dale Carnegie reminds, “It’s much easier to become interested in others than it is to convince them to be interested in you.”  And if both parties follow this skill, the conversation should be quite balanced leaving each party partaking in a pleasant conversation.

8. Refrain from Over-Sharing

While sharing all of your “war” stories, relationship gaffs or children’s accolades may be something you are quite comfortable with, don’t assume those you are conversing with will be. Proceed slowly when it comes to sharing personal information – test the waters to see how comfortable others are with certain issues before diving right in. And when in doubt, don’t ask.

9. Practice Humility

While accepting compliments should always be done with gratitude, making sure to point out others’ contribution is a way to display humility and build respect. Listening to someone drone on about how successful they have been (humble brags should be kept in check as well) is not an engaging conversation starter. Often such successes will come up naturally, and when they do you should absolutely own them, but then revert back to the first sentence of the paragraph.

10. Seek to Understand Rather Than Be Right

We’ve all run up against certain conversationalists that are adamant about their point of view being the only proper way to see the world. These people send people scattering to everyone else’s conversation except their own. Why? They’d rather be right than consider other perspectives. Even if they walk away with their mind’s unchanged, a brilliant conversationalist will invite other viewpoints, sincerely consider them and see the colloquy as an opportunity to finesse their point of view or broaden their understanding.

11. Adhere to Omission When Necessary, But Always Speak the Truth

Similar to #2, if you know that certain information will hurt somebody in the conversation or would be inappropriate in a particular setting, refrain from bringing the information to the table. If asked directly, be honest or simply say, “I don’t feel comfortable talking about it here.” Either way, maintain your intriguing while respecting the scenario you are in at the moment. After all, you are not in the court room or behind closed doors with our close confidants.

12. Be Cognizant of Your Audience

Tying in with #11, knowing your audience – who will hear you – what their backgrounds, beliefs, ages, are is crucial to best deciding what would be the appropriate and most engaging conversation to percolate. Everything isn’t open for discussion all of the time, and a tactful conversationalist recognizes this.

13. Brush Up on Current Events

One of the best ways to always be prepared at a gathering in which you won’t know many people is to get caught up on the current events of the moment. Whether local, national or world news, politics, sports, films, books, or weather, these are always great topics to have in your bag of tricks to jumpstart a conversation with an absolute stranger.

14. Brevity Provokes Curiosity, Long-Windedness Kills the Flow

Have you ever listened to someone telling a story and they decide to go back months prior to provide context, and upon the story finishing up, you realize there was no need for all of the extra details? Don’t be that person. It’s better to share just enough or a sliver shy of enough and prompt questions of clarity than to drone on leaving you as the only one speaking and everyone else wondering what the point of the story is.

15. Respect Comfort Levels

A sense of mystery is always a respectable quality to have, and that also means respecting others’ privacy. Only ask questions in which you know they are comfortable with and don’t assume simply because you are, they must be too. A skilled conversationalist will remember past conversations they’ve had with individuals and remember what topics people enjoyed discussing and which have never been discussed. One of the ways to test the waters is to share similar information about yourself. After all, if you aren’t comfortable talking about certain subjects, don’t expect your guests to feel comfortable with you.

16. Navigate Disagreements Respectfully

Personally, I enjoy conversations where there is great banter, but if one of the parties involved doesn’t understand how to do so tactfully, it can end in disaster. However, if both parties do, it can heighten the conversation and provoke even more thoughtful discussion and engagement. First, if you disagree with the opinion stated, begin by finding the common ground. What do you agree with, what do you see eye-to-eye on. For example, if you’re talking about the Congress’ inability to compromise, but you disagree with what they feel the problem is, begin by stating, “I couldn’t agree more. Congress certainly needs to change the way in which they function because it isn’t efficient or helpful to the country.”

By pointing out common ground, you are acknowledging you have listened and you have validated the premise that inspired their opinion.

Second, following the initial common ground statement, transition with the conjunction “and” rather than “but”, which is akin to hearing the phrase “We need to talk” – an absolute mood killer. When you use the conjunction “and” you are adding, not deflating the conversation. For example, ” . . . and  while [insert their opinion] is one idea, another solution may be [insert your opinion and brief explanation].”

17. Comment on Topics of Common Interest

Often a gracious host/hostess will introduce their guests to others offering a bit of information that will help a conversation begin – their profession, where they’ve lived or traveled, etc. When you discover a common interest, start the conversation there. If you find yourself in a situation where there is no hostess, begin with the location – have you just ordered the same pastry? are you listening to a particular musician on stage? Start there and see where the conversation takes you. It all begins with basic observational skills of your environment. Often there are more clues and conversation starters around you than you realize.

18. Put the technology away

Conversation requires two attentive parties engaged in listening, and playing off of what each other has said. Imagine a tennis match. The only way for the ball (conversation for our topic) to stay in play and move forward is for both parties to be giving their full attention to those talking, not looking at their cell phone. Not only will the point (conversation) come to a quick end, it is rude and disrespectful (exceptions – a work environment, emergencies, etc).

19. Be Privy to a Conversation’s Natural End

End any conversation – formal or not – on a positive note, even if interrupted, and be sure to smile and convey that you enjoyed the conversation before moving on.

While each of these 19 tips are guidelines to keep in mind, part of the reason diving into a conversation is so daunting is because so much is out of our hands. While that can be intimidating, it is also what makes conversations so exciting to be part of. You never know where they will go, who you will meet, what you will learn, etc. And if you break a few rules along the way, if you’re paying attention to the people involved, you’ll get a good feel for what people are comfortable with. Simply pay attention. Part of not only conversation, but life, is simply being aware in the moment of yourself, those around you and the environment in which you find yourself.

The great charm of conversation consists less in the display of one’s own wit and intelligence, than in the power to draw forth the resources of others; he who leaves you after a long conversation, pleased with himself and the part he has taken in the discourse, will be your warmest admirer. Men do not care to admire you, they wish you to be pleased with them; they do not seek for instruction or even amusement from your discourse, but they do wish you to be made acquainted with their talents and powers of conversation; and the true man of genius will delicately make all who come in contact with him feel the exquisite satisfaction of knowing that they have appeared to advantage.” —Jean de La Bruyère (French philosopher and moralist)

~Join the Conversation – what you have you discovered to be effective ways to perk up any conversation? Please do share. 


~A Little Privacy Please

~Why Not . . . Become a Better Listener?

~Why Not . . . Have That Difficult Conversation?

Thesimplyluxuriouslife.com | The Simply Luxurious Life

5 thoughts on “19 Simple, Concrete Tips for Mastering the Art of Conversation with Anyone

  1. Hi Shannon,
    Thank you, as always, for such a wonderful, helpful and thought-provoking post. I read and reread your posts with pleasure, and I have found this one particularly resonated with me. I also believe strongly in the importance of conversation; indeed, I believe that good conversation with close family and good friends is one of life’s greatest pleasures. The late, great Irish poet, Seamus Heaney, understood such moments beautifully: he described the particular pleasure of enjoying such good conversation that he knew, even in the moment of conversation, that he would look back on it later with pleasure too: “It felt remembered, even then.” I love that line – and I love it when such memorable moments occur in my own life, and I notice them both at the time and then again later as I reflect upon the joy of them.
    Thank you for inspiring us all to seek such moments!
    Have a lovely day.
    Best wishes,
    Anne in Ireland.

  2. Shannon,
    I read your post on and off and while I loved reading “The Art of Conversation”, I just think using the phrase “a brain-fart moment” goes against what you’re about. It’s not French, it’s not lovely, it’s just a gross figure of speech that makes me cringe when I hear it said, lest of all a guide for living well and speaking well.

    Recently a waitress forgot an order for a member of our party and stated she’d had a “brain-fart”. When she walked away, we all just looked at one another in disbelief. How unappetizing!

    Thank you for listening.
    Mary Fanara

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