Let’s Talk to Other Personality Types: The Art of Conversation

Darrell’s avatar

“What ho!” I said.
“What ho!” said Motty.
“What ho! What ho!”
“What ho! What ho! What ho!”
After that it seemed rather difficult to go on with the conversation.

P.G. Wodehouse

A Generous Conversationalist No Matter Your Personality Type

A good conversationalist is a generous conversationalist. Few of us are narcissistic enough to expect to do a one-sided stand-up routine when we talk with others. We want good back-and-forth, and listening is essential to that. However, to be a good listener, we need something to listen to. We need to learn to engage people in conversations that bring them out and allow them to talk about themselves and their worlds. Sometimes people are reluctant to speak, but they still may want to connect – even the quietest Introverts. Mostly, people want to feel heard.

Conversing across personality types can be a little like speaking a foreign language. Assuming you’re not French, you might get a cup of coffee in a Paris shop using another international language, but you might win a Parisian’s heart if you try their language instead. Allez-y, soyez courageux!

Same with how we approach people. Sometimes we need to learn how to speak other people’s “language.” That doesn’t mean you have to stop speaking your own personality’s tongue. You don’t become less “you” when you try to connect with someone else on their terms. You can stay true to yourself while committing an act of generosity and respect.

Good chatters usually keep a couple of handy tools in their toolboxes, such as an assortment of reliable methods and a measure of common sense. The art of conversation is mostly developed through practice, and there is no adequate guide besides experience. As with many things, it takes practice, practice, practice.

What we offer in this article is mostly general. We provide broad guidelines (including Roles instead of specific types or traits) for reaching out to other personality types at your job or in your social circle. Where the expert conversationalist might use a scalpel, this article is offering a mallet. You’ll probably have to fine-tune what we provide here for the unique individuals you meet. But this may point you in the right direction and get you started.

The general guidelines offered here come from our theory, experience, and some data from our polls. The viewpoint is one of you trying to engage another person with specific personality traits. By now, it’s assumed, you already know your own strengths and weaknesses. (If not, much is available throughout our site, and this might be an excellent time to take our free personality test if you haven’t already.) You already know your own interests. Now, let’s work on focusing your conversations when talking to different personality types.

Chatting with Analyst Personality Types

“The most fruitful and natural exercise for our minds is, in my opinion, conversation.”

Michel de Montaigne

Breaking the Ice

To get an Analyst’s attention, you probably won’t get far with the usual small talk. They’re probably too busy in the far reaches of their imagination to worry about anything trivial. (“Nice venue, huh?” may not impress them. “Yes, it is.” Putt... putt... the conversation stalls and begins to spin toward the ground.)

You might have more success if you offer something that takes a bit of dissecting. Maybe an opener that starts with, “I wonder why...?” such as, “I wonder why they chose St. Louis as the city to hold the conference...” “I wonder why they picked this year’s theme...” “I wonder why they don’t offer a salad with their tacos...” (Repeating “I wonder why...” may get a little annoying, so mix it up.)

Analysts often think in terms of “why,” “how,” and “what if.” While there are no guaranteed topics, the likelihood of engaging an Analyst personality type will increase with an open-ended question that requires a little examining of the facts.

Going Deeper

Get them to talk about practical issues from the viewpoint of how they might be improved. “I’ve often wondered how we can spend less money and still train all of our employees...” “I never know how to fit everything I need to do into my schedule. How do you handle your calendar?” Give them a little puzzle to work on.

Then, gently and politely, challenge them. While Analyst personality types are not any more likely to enjoy their ideas being challenged than anybody else, they often take pride in defending a position. Announcing that you’re playing devil’s advocate not only takes away the feeling that it’s a personal affront, but also suggests that you are looking for more information. Any time you look for clarification, it might appeal to Analysts, who will likely enjoy explaining things to you.

Typically, individuals with the Intuitive and Thinking personality traits are too busy constructing ideas in their heads to be paying complete attention to you anyway. Unless they see you as an expert – or, at least, on their level – they may not always be listening. You’re probably not going to change that. But your silence can be a very potent conversational skill when meted out at the right time and in the right measure. So, patience.

Getting the facts out or a problem solved will be more important to Analysts than making sure everybody has a turn at speaking. Your best chance for gaining the stage, if you must have it, is to offer some interesting new information to Analysts, especially if it’s a challenging idea.

Things to Avoid

Avoid making claims you can’t back up. Offering theories to an Analyst personality puts you where you want to be – in their ballpark. Just make sure your theories have credible foundations, or you’ll lose respect and probably any measure of engagement you’ve earned.

Avoid the warm and fuzzy as a rationale. While Analysts are capable of empathy and caring for people when called upon to do so, they rarely look at the world through that filter. “If we did that, the human resources people would be miffed,” might produce a shrug from them. Too much “touchy-feely” soft discussion and they might wonder how serious you are about the issues you raise.

Chatting with Diplomat Personality Types

“Manners are the ability to put someone else at their ease...by turning any answer into another question.”

Tina Brown

Breaking the Ice

Focusing on the human condition is exactly the thing that grabs Diplomats’ attention. Talk about the humanity of a situation, and you’ll watch their metaphorical ears perk up. “My goodness. I can’t believe the restaurant is making those people stay outside in the freezing rain while waiting for a table.” “Did you read the news about the refugees? Isn’t that terrible?” “Isn’t Betty hilarious? She’s become much friendlier lately.”

Going Deeper

Many Diplomat personalities love a cause, whether it is on a local level or something more global. Discovering what their causes are, and their beliefs or behaviors around those causes, will encourage them to share. Big ideas about social matters resonate with many Diplomats. Sharing your own causes, if you have any, may reveal a kindred spirit and lubricate the conversation.

Highlighting a problem and brainstorming a solution may also work. “I felt they humiliated Janet at the meeting today. I wonder what we can do to help her out?” “I heard one in five people go to bed hungry. But what can the average person do?”

Diplomat personalities not only advocate for improvement in societies and communities, but on a more micro level, they are often fans of personal development. Some may be interested in spiritual evolution. Topics around human growth often intrigue Diplomats and may pull them deeper into a conversation. “I took up yoga a few months ago. It’s made a world of difference. Have you ever tried it?” “I’m trying to read at least an hour a day again. I became so busy... I really missed it. Do you find time to read much?” “I’m trying this new technique for curbing bad habits...”

Things to Avoid

Unless you’re up for a heated response, avoid saying anything that makes people sound like an inanimate cog in the machine or just a number. An Analyst personality might shrug when someone says, “If we did that, the human resources people would be miffed,” but that same statement is likely to worry the Diplomat. They may shut down. Statistics about human suffering are often met with disdain. “So what if unemployment is down to five percent? Sure, that’s better. But try being one of the five percent.”

When speaking with a Diplomat, learn to go with the flow and avoid being offended or defensive when they don’t seem to connect the way you expect. Intuitive personality types tell us they spend more time than their Observant counterparts anticipating what they will say next instead of listening.

However, the sense that they aren’t relating may be somewhat lessened by Diplomats’ Feeling personality trait. For them, it’s all about harmony and understanding. Diplomats will try to give equal time (or more) in the conversation out of a sense of fairness. They try to genuinely hear what others have to say. Even so, this may always compete, at least a little, with their busy imaginations. They may not always sound like they are on the same track as you, but it doesn’t mean they aren’t processing your information. They may be doing so, but in their unique way. So, don’t give up.

Chatting with Sentinel Personality Types

“As far as I am concerned, philosophic questioning is just as likely to make you confused and depressed as it is to improve your condition.”

Christopher Paolini

Breaking the Ice

Small talk is about noticing and commenting on the everyday things around you. Sentinels, with their Observant personality trait, are all about the present and concrete world. Small talk is generally just fine with them. Ask about their job, their hobbies, or their family and friends and let the conversation roll. Even Introverted Sentinels highly value connection and the idea of community – whether they are active in it or not. Their work, families, and communities are likely hot topics.

Going Deeper

Sentinels love to talk about how life is going or how it should be going. They enjoy practical issues and current matters. They are loyal to the people and things they value in their lives. They can also be status-oriented, so talking about homes, cars, vacations, and children might help spark conversations, depending on the Sentinel type.

Those Sentinels who prefer the Thinking personality trait might be interested in things that involve procedures and making a system run well. A horror story about some logistical nightmare is good fodder for talk at work. Those who rely more on the Feeling trait may highlight the people in their lives. They are warm and empathic listeners and like to share stories about more personal matters.

Sentinels rarely seek praise but are thrilled when others recognize their efforts. Bringing some honest and well-placed compliments into a conversation pleases most people. These hard-working personality types appreciate it (and maybe even deserve it) more than most.

Things to Avoid

Observant types are not so interested in theories unless they have a very direct connection to some practical outcome, so “keep it real.” Fantasy also has its limits in conversations with them. They may enjoy a movie about superheroes and their missions to save mankind. The sense of duty may appeal to them. But don’t get them into an argument about whether Iron Man can take down Captain America. That can seem way too silly to Sentinel personalities.

Avant-garde ideas and trendy things also have a short shelf life. Something along those lines may strike them as interesting...but only for a minute. There are too many real-life matters to talk about. Sports, politics, fashion, or anything actual and conventionally real in their lives might be a good substitute when the conversation gets too “out there.”

Sentinels’ loyalties run deep, so be careful if you are critical of someone or something they feel strongly about. Some people don’t mind going negative on families or jobs during a chat. Sentinels may take offense when they do. They often identify too closely with these parts of their lives and are put off by displays of such opinions.

Chatting with Explorer Personality Types

“Sometimes the greatest adventure is simply a conversation.”

Amadeus Wolfe

Breaking the Ice

Typically, when other people are talking, Explorers are doing something, thinking about doing something, or on their way to do something. That doesn’t mean they can’t stop long enough to be great conversationalists. Many of them love talking about what they are doing.

One way to get an Explorer talking is to ask about their latest project or mission. It isn’t so much the conceptual stuff that interests them, and they’d rather focus on the activities involved. “How exactly would you do that?”

No matter what they do for a living, Explorer personality types are the skilled, hands-on performers and artisans among us. Usually, there is a lot to spark a conversation there. “When you sing like that, how in the world do you hit that high note?” “Have you been rebuilding engines long? When was the first time you rebuilt one?” “They change the steps for CPR so often. Right now, it just confuses me. As a first responder, you must know the best way to resuscitate a person.”

Going Deeper

Explorer personalities often like to be the heroes of their own stories, but this isn’t necessarily about egotism or narcissism (although that might sometimes be there). They get much of their self-esteem from being useful. And, consequently, they like having their skills recognized. “Skilled” is more or less their brand.

So, they like when their expert handling of something is played up either by themselves or someone else. It validates who they are. Getting them to tell a story about how they agilely saved the day or used their talents to make a difference will usually engage them. Imagine your Explorer wearing a button that says, “I’m good in crises. Ask me how.”

Explorers often like things that are trendy and cutting edge, and talking to them about the latest in anything that interests them will keep them in the conversation. Conversations about a superior new technique for doing anything is perfect.

Some Explorers with the Feeling personality trait see themselves as counselors or sometimes mentors. Asking the advice of individuals in this subgroup may also stoke the conversational fires.

Things to Avoid

As with their Observant cousins, the Sentinels, Explorer personalities stay away from theory and are more interested in concrete matters that can be physically manipulated. If the conversation turns too much to what exists solely in someone’s mind, you might lose them. However, translate that theory into real action, and you’ll get them back.

Be careful not to judge them for taking risks or departing from conventional methods. These personality types are so utilitarian that they sometimes feel fine with rules being broken, and sometimes they find it necessary to take risks to do things. They will simply think you don’t get it if you criticize. While you don’t have to approve of their unorthodox methods, when talking with them, withhold judgment. (Unless it’s your job to keep them in line.) You might even draw them in by praising their ingenuity and boldness without condoning their methods.


People are not usually compliant enough to be so cookie-cutter simple. People are too complex to make communicating so one-dimensional and easy. You won’t find the absolute Analyst, Diplomat, Sentinel, or Explorer out there. These are only guidelines that may help if you feel like a conversation is hard to start, or your conversations have hit the doldrums.

No matter what technique you use, the final goal is to exchange thoughts, emotions, facts, or ideas in a genuine and spontaneous manner. It’s about connecting with another person. If you lose that, it’s just so much talk.

How are your conversational skills, and how do you think your personality type affects them? What are some tips you can share about talking with people who have traits different from yours? Tell us about it in the comments below.

Further Reading

Waiting to Respond: Who Listens and Who Doesn’t During a Conversation

The Mystery of the Talkative Introvert

When the Need to Connect Becomes Terrifying: The Dilemma of the Shy Extravert

Telling Stories at Parties: Which Personality Types Do It Best?