If a conversation ends after “So what do you do?” … things can get awkward.

At this point, we don’t know what else to say. We stink at small talk. We are shy. We are insecure. We’re introverted. Whatever the reasoning or logic, awkward conversations are, well, awkward. It’s uncomfortable for everyone.

But no one wants to feel awkward. We want to be liked. We want to be charming. We want to be charismatic. But that's a natural instinct, rooted in our psychological desire to belong, as illustrated in Maslow’s Hierarchy of Needs:


So that brings up the question -- what are the psychological habits of the most likable, charismatic, and charming people?

To uncover the trends, we dove deep into research and studies of behavioral psychology. So if you want to transform from awkward and shy, to charming everyone you meet … check out the following tips, validated by countless studies and research.

1. They have positive and negative empathy.

People who possess positive empathy don’t get jealous, they get excited. They are thrilled when:

+ Someone else decides to quit their job and travel in South America for 6 months.

+ Someone else gets their dream promotion (or hired at their dream company).

+ Someone else gets their business acquired for $100 million.

Negative empathy is the ability to comfort others when they’re down. People who posses this trait will:  

- Help someone when their family member gets diagnosed with cancer.

- Support someone when they get fired from their dream company.

- Comfort someone when they break up with their significant other of six years.

Positive and negative empathy is the ability to put yourself in someone else’s shoes and genuinely feel what they are feeling — either good or bad.

In fact, we even had a part in our brain dedicated to empathy called the Right Supramarginal Gyrus, that triggers empathetic responses:


We are physiologically and psychologically hardwired to help people (i.e. feel empathetic). The trick is feeling it for both positive and negative events.

Action Step: Take an Emotional Intelligence Quiz.

Emotional intelligence is an incredibly valuable skill, which was found to be the strongest predictor of performance. Research from TalentSmart explains emotional intelligence is responsible for 58% of success in all jobs.

In a nutshell, emotional intelligence is the ability to feel what someone else is feeling. The ability to be empathetic and put yourself in their shoes.

Test your knowledge by taking this free emotional intelligence quiz from the University of Berkeley-California.

2. They are humble.

This quote sums it up perfectly:


Humility is not thinking less of yourself, it’s thinking of yourself less.

- C.S. Lewis   

People who are genuinely enjoyable to be around are humble, not arrogant. They don’t wave awards in people’s faces. They don’t name drop for the sake of sounding important. They don’t toot their own horns. They don’t have an aura of I-am-the-coolest-person-in-the-world.

Of course, it’s healthy to be confident and sustain a high self-esteem. But there’s a fine line between confidence and arrogance. And the difference is humility.

It separates those enjoyable to be around versus those you can’t stand:

Think of Kanye West — he’s incredibly successful, yet incredibly obnoxious. Now think of Barack Obama — he’s incredibly successful, yet incredibly humble.

Love or hate Kanye West’s music, there is no denying his supreme confidence and arrogance. Agree or disagree with Obama’s policies, there’s no denying his supreme confidence and humility.

There is a fine line … and people who are enjoyable to be around avoid egocentric, self-centered bragging.  

Action Step: Observe the patterns of humble people.

One of the easiest ways to practice humility is to observe the patterns of humility of other people. Take this video of Bill Clinton and Nelson Mandela meeting:

You see them smile, stare deep into each others eyes, touch each other on the shoulder, and nod in as if they’re bowing. They are showing respect and courtesy.

3. They are vulnerable.

Vulnerability is uncertainty. It’s putting yourself out there to risk embarrassment or judgment. That definition can become foggy, so here are a few examples: 

  Vulnerability is approaching a stranger in a coffee shop, asking them on a date.

  Vulnerability is giving a presentation to 195 people, even when you’re scared shitless of public speaking.

  Vulnerability is stating your conflicting opinion, when nine out of ten people in a room all believe the same thing. 

Brene Brown, a social psychologist with 10 years of experience of studying vulnerability, gave one of the most watched TED Talks of all time at over 20 million views: 

Let’s be clear — being vulnerable isn’t easy. It’s one of the most emotionally challenging hurdles one can face, overcoming the fear of being judged or criticized.

Yet incredibly likable people aren’t afraid to open up. They aren’t begging for approval from others, so they have no desire to come off as a perfectionist. Furthermore, they realize that those who do appear as perfect may actually be less likable.

When someone appears perfect, we distance ourselves from them. When they appear flawed, we’re attracted to them. This psychological phenomena is known as The Pratfall Effect:

rule-of-reciprocity-email-networkingThe Pratfall Effect 

By making a mistake, or admitting to a mistake, we become more likable. Studies prove people connect with those who admit their flaws, versus those who appear as perfect all the time. 

By being vulnerable, we prime ourselves for failure. Through failure, we become more likable. Thus, vulnerability has the power to trigger likability. 


Out of your vulnerabilities will come your strength.

- Sigmund Freud    

Action Step: Do a Stranger Photo Challenge.

So you’re afraid of feeling awkward or vulnerable? Try out this “failure challenge” by the CEO of SumoMe, Noah Kagan:

1. Find a complete stranger to take a picture with you.
2. Have them hold a sign for proof (see sign here).
3. Upload photo.

See more details on this page.

4. They have a sense of humor. 

Watch this 30 second clip:   

Now don’t you just like Old Spice a little bit more?

They’re leveraging a psychological effect called the Peripheral Route to Persuasion. Since it’s a low cognition product (i.e. I don’t think of what deodorant to buy for more than a few seconds), they’re leveraging humor as a “liking cue” to create a subconscious inkling to purchase Old Spice as a quick decision amongst competitors. 

In layman's terms, that means when I’m walking through CVS searching for the magical slimy stick of chemicals (what is deodorant made of anyway?) and see Old Spice … I can’t help but grabbing it. 

Validating their logic, in a study conducted by the American Psychological Association, people who were exposed to humorous ads for low-cognition products were vastly more likely to purchase the product. 

But here’s the crazy part — people HATE ads. So if ads alone can make someone smile … surely so can another human. 

Think about it. When is the last time someone you just met cracked a joke and you thought, wow I hate guy/girl. Probably never. 

It seems obvious, but people who are enjoyable to be around genuinely have a great sense of humor.

Action Step: Try the 5-5-5-5 email joke experiment.

Think you’re not funny? Sure you are. Schedule to send 5 emails over 5 days at 5pm, BCCing 5 different people. 

1. Go to this subreddit called /r/3amjokes. It’s sorted by the best one-liner jokes of all time.

2. Pick your 5 favorite jokes.

3. Write an email with the question in the subject line and the answer in the body:

4. Schedule an email to send at 5pm, BCCing 5 different people. After downloading HubSpot Sales, just click the clock icon by the send button and choose your time:

5. Repeat this to schedule emails for 5 consecutive days at 5pm. It will take less than 5 minutes.

Because who doesn’t want to get a corny joke in their inbox at 5pm after a stressful day of work?

5. They are present.

How frequently does this happen?


Yet, I’m not one to judge. I’m guilty of this from time to time as well. However, I’ve basically ended my smartphone addiction by keeping my phone on Do Not Disturb 24/7:

When our phones vibrate, we are curious. Who texted us? So we check to find out. As a result, we’re distracted from the face-to-face-conversation. This makes it seemingly impossible to have a productive face-to-face conversation.

Similarly, it’s difficult talking to someone who is completely tuned out of a conversation. A wandering mind is far more difficult to fix than clicking a button on your phone. But just because it’s difficult, doesn’t mean it’s impossible.

I’ve had my fair share of mind-wandering problems, thinking about other things going on in my life during a conversation, but one method I’ve found to help is meditation. And I’m not the first (or last) to preach about the powers of meditation. These successful people also practice meditation:  

  • Mark Benioff (CEO of Salesforce)
  • Arnold Schwarzenegger
  • Oprah Winfrey 
  • Tim Ferriss (entrepreneur and author)
  • Martin Scorsese (film director)
  • Ray Dalio (hedge-fund manager)

If you’re struggling with being present during conversations, I suggest giving meditation a go.

Action Step: Practice meditation for 10 minutes a day.

Download Headspace, an iPhone and Android app that guides you through the basics of meditation, in 10 minutes per day.

I've tried plenty of other applications and methods, but I've found nothing better than Headspace to learn the basics and get started. All in just 10 minutes per day. Plus, it's free.

6. They are genuinely interested in EVERYONE.

When you see this, how does it make you feel?


If you’re like 99% of humans, it makes you smile and say “awwwwww, GIMME THAT DOGGY!!!” 

Why do dogs make us feel this way? Why are they so lovable?

Perhaps because they are genuinely excited to greet EVERYONE. They don’t pick and choose who they are excited to meet for the first time, or see for the second time.

Remember how likable people are humble? Well, they’re also not pretentious.

That means they don’t hold a chip on their shoulder when dealing with someone who is “under” them. They are genuinely interested in what EVERYONE has to say. They want to hear their story.


Charisma is not so much getting people to like you as getting people to like themselves when you’re around.

 - Robert Brault   

Action Step: Try “The Server Test.”

Ever been to a restaurant and someone is extremely courteous to you, but is impolite to the waitress or waiter? 

That’s the server test. 

Next time you’re considering a new hire or business partner, take them out to lunch. Then see how they treat the server. It’s a judgment of character outside of the realm of impressing the person above them. It shows they are kind and genuine to all people, not just those who they’re trying to impress.

Hat tip to Jeff Haden for this incredible bit of advice. 

7. They avoid social narcissism. 

Guess what the favorite topic of conversation is for a social narcissist? Themselves.

They want to talk about their stories. Their problems. Their successes. Their complaints. Their family. Their friends.

45 minutes later, it’s time to split ways and they haven’t once asked about the other person’s past, present, or future.

Instead of rambling about how amazing (or terrible) their lives are, likable people ask questions. They dive deep into the minds of the person they’re talking to.

Not surface-level, small talk questions such as where are you from? Or what do you do? Or how about that weather today?

But they dive deep, asking open ended questions, uncovering the emotions and motivations of people. They ask questions that will make the other person feel good — or ask themselves questions. They ask open-ended questions. They ask why. They show genuine interest.

Action Step: Ask open-ended questions.

Getting stuck in a conversation? Or it feels like a dead end? Try asking open ended questions. As soon as you learn a little about someone, ask:

  How did you do it?

  Why did you do it?

  What did you struggle with most?

  What was the most valuable lesson you learned from that?  

You’ll be surprised how far a conversation can go when the “yes/no” questions are avoided.

8. They are generous and altruistic.

According to Adam Grant, the youngest-tenured and highest-rated professor at Wharton School of Business, there are three types of people:

1. The Taker

2. The Matcher  

3. The Giver

The Taker is an egoist. They tend to get more than they give. They believe the world is a competitive, dog-eat-dog world. As a result, they put their needs before everyone else. This strategy works for short-term gain … but it’s nearly impossible to sustain.

The Matcher is someone who seeks balance between giving and taking. They seek fairness and equality. If they put too much into a relationship, without getting anything in return, they’ll eventually give up. They believe in even exchanges and trading favors.

The Giver is altruistic. It’s a rare breed of human who doesn’t look for anything in return. Whereas Takers are focused on receiving all of time and Matchers are focused on receiving at least some of the time … Givers don’t even think about it.

By giving and giving and giving … you also increase your chances of receiving value in return:

It’s incredible how far you’ll go by being generous and altruistic, putting everyone else’s needs before your own. 

Hiten Shah, CEO of KissMetrics, is the epitome of a giver. He even boasts an inspiring Zig Ziglar quote on his Twitter homepage:


From the man who started two wildly incredibly successful software companies (Kissmetrics and Crazy Egg) … I’d take that advice to heart. 

Action Step: Be honest with yourself ... 

Ask yourself the following:

When I’m helping someone, do I expect a favor in return?

If you answered yes, you may be a Taker or a Matcher. If you answered no, you may be a Giver. Honestly consider the power of giving without expectations. You'll be surprised how far it will take you. 

9. They reciprocate praise (and take blame). 

When a likable person is praised for their work, they typically have a response like this: 

Thank you so much! However, I’d like to emphasize that this was a team effort. I played only one small role in hitting this goal. Jen, Sam, Mike, and Kelsey … you were all crucial to making this happen. And we wouldn’t have done it without you.

In other words, they give credit where credit is due. When they’re recognized for a success, they shift the praise toward everyone else. They give praise and empower people without expecting anything in return.

Conversely, when shit hits the fan, they aren’t afraid to take the blame.


A good leader is a person who takes a little more than his share of the blame and a little less than his share of the credit.

- John Maxwell   

In fact, that’s what HubSpot Sales growth marketer, Anum Hussain, did when a $500,000 project went downhill very, very quickly. 

She immediately took blame for the mistake. As a result, everyone forgave her, which actually strengthened her relationships. This psychological effect is known as The Pratfall Effect, which we touched on earlier.

Action Step: Adopt The Pratfall Effect.

Was a project screwed up that you had part in? Or did you directly screw it up? Follow the step-by-step process highlighted in this piece about The Pratfall Effect:

1. Admit your mistakes

2. Fix your mistakes immediately

3. Send a post-mortem analysis on what went wrong … and how to prevent it in the future

Read more about how Anum Hussain admitted failure of a botched $500K project, which actually strengthened her relationships.

Summary: 9 Habits of Insanely Likable and Charismatic People

As a quick summary, here are the 9 habits of insanely charming and charismatic people: 

1. They are empathetic

2. They are humble

3. They are vulnerable

4. They are have a sense of humor

5. They are present 

6. They are genuinely interested in EVERYONE 

7. They avoid social narcissism 

8. They are generous and altruistic 

9. They reciprocate praise (and take blame)


Want more? Learn 125 conversation starters for any situation next.

Get HubSpot CRM today!

Originally published Jan 25, 2017 8:00:00 AM, updated December 14 2017


Building Rapport