Why Can’t I Start a Conversation with You? (Part 2)

Picture this: you’re standing in a room full of strangers, not talking to a soul. You’re hoping to make at least one connection, but can’t seem to get the ball rolling. Eventually you think, “This is ridiculous. Why can’t I start a conversation with anyone?”

The answer to that question runs deeper than you might think.

Starting conversations not only depends on your communication skills; it’s also a function of your self-confidence. In this article, we will explore 9 common barriers that stand in your way of conversational approachability.

BARRIER #1: I don’t want to be rejected.

This is the big one. The number one hindrance to approaching someone else: the fear of rejection.

In Triumph Over Shyness, Philip Zombardo states, “Shy people are often attracted to those who do not return the affection, which is a very painful way of creating safety.”

Yes, it can be scary. But the truth is, rejection is part of life. You can’t evade it forever. Also, assuming that you can’t handle rejection is a mistaken belief. Besides, more often than not, rejection isn’t as bad as you think. After all, what’s so bad about being rejected by someone you hardly even know? Don’t let a few no’s stand in your way of stepping up to bat again in the future.


Win a few small victories first. Go to the mall and practice approaching cashiers, clerks, salespeople, kiosk operators and the like. They can’t reject you! These smaller successes will build your confidence and equip you with positive experiences to dwell upon in the future.

BARRIER #2: I don’t have anything good to say.

First of all, 93% of all conversation is nonverbal. So, don’t get too hung up on your words. Concentrate on having approachable, open body language first. Smile, don’t cross your arms, maintain open posture, keep your hands away from your face and maintain eye contact with everyone within 4-10 feet of you. Many people – even extroverts – miss the boat on this crucial component of communication.

Secondly, consider this: the only thing people can judge about you is how engaging with you makes them feel. It’s like Mother Theresa said, “People won’t remember what you said, or what you did; but they will never forget the way you made them feel.”

And finally, who says there’s a “right” thing to say all of the time? Not everything you say has to be supremely witty, brilliant or quotable. Again, the secret isn’t in what or how much you have to say, but in how you make people feel. Focus less on YOUR self, YOUR insecurities and YOUR discomfort, and more on the conversational needs of others. Be a great listener. Ask open-ended questions that begin with “What’s your experience?” and “What’s your favorite?” An increased focus on others will help you overlook your own insecurities.


If you don’t think you have anything good to say, make a “Conversation Cheat Sheet” before you leave the house. Grab an index card and write out the following: three great questions, three interesting pieces of information, trivia current points of interest and three of your favorite stories you’ve told a million times. That should be enough material to last for weeks!

BARRIER #3: I don’t want to waste that person’s time.

This belief is based on the mistaken assumption that you’re not worth talking to. That you’re not good enough for a few minutes of someone’s precious time.

Wrong. An attitude like this characterizes a negative self-image, which often stems from negative past programming. For example, it’s possible that someone you know – a parent, a teacher, a boss – probably told you “you’re not good enough,” “you don’t matter” or “you’re worthless” in the past.

Sadly, harmful comments like these have a profound effect on the future of your approachability.

HERE’S THE SECRET: in Shad Helmstetter’s What to Say When You Talk To Yourself, he explores the power of your thoughts. His work proves that if you first flood your mind with positive thoughts, you will enhance your self-belief. If you enhance your self believe, you will change your attitude. And if you change your attitude, you will change your actions.

Therefore, the key is simple: change your programming.


Every morning for one month, read a series of positive, attitude building affirmations. It might sound like a silly exercise, but this stuff works! Try phrases like “I am a confident communicator,” “shyness is not a problem for me,” “I am willing to step out of my comfort zone,” and “I feel relaxed when I communicate with new people.” These affirming phrases are almost certain to raise your confidence level.

BARRIER #4: I have a toothache.

In other words, you’re TOO tall, TOO old, TOO ugly, TOO new, TOO young, TOO inexperienced and the like. Really? According to whom? Is that what YOU believe; or is that what your friends, parents, the media and others have told you about yourself?

Either way, consider these three facts:

FACT #1: You are what you are because of the way other people see you. We never call ourselves a name until someone else offers us that label first. Interestingly, that happens to be the leading characteristic of most shy people: others tell them that they’re shy.

FACT #2: Change in attitude = change in how you act = change in how people see you = change in how you see yourself. So, cliché as it may sound, it all starts with a positive attitude about yourself. I think Norman Vincent Peale said it best: “Since you must sell yourself before selling your goods, you must sell yourself on yourself. So believe in yourself.”

FACT #3: You are your own worst critic. You are a biased observer and will see what you want to see, not what other people truly see. Remember that.


Make a list of all of your “toothaches.” Then, reverse them and put “I believe” in front of each along with a positive attribute. Instead of “I’m too old,” write “I believe my age gives me wisdom and experience that can help others.” Read this list to yourself every morning. These affirmations will reprogram, reinforce and rebuild your self-image.

BARRIER #5: I will embarrass or humiliate myself.

Says who? You have absolutely no way of predicting such outcomes. Zombardo (ibid.) explains that shy people often assume they will be embarrassed because, at some point in the past, they were once embarrassed. They are dwelling on the reality of the past rather than the potential of the future.

They key to overcoming this assumption is twofold. First, you need to put a few points on the board. In other words, concentrate on your past victories. Think about the last few times you engaged in successful conversations. Did you laugh all night with your new friend? Develop a new relationship? Make a valuable business contact? If you search your memory, you’re bound to uncover a few gems from your past when you “did it right.”

Secondly, think about the myriad benefits to meeting someone new: learning, laughing, expanding your network, having fun, sharing opinions and experiences, connecting with new people, even better health!

That’s right, better health. Check this out…

According to a recent issue of Psychology Today, we might have a better time–and go home in a better mood–if we chose to make new acquaintances. In 2005 a University of Pennsylvania psychologist randomly assigned college students to bowl by themselves, with close friends or with complete strangers. To the doctors’ surprise, they found participants who spent their time with strangers were happier than the students who handpicked buddies to accompany them.


Next time you attend an event, try to split your time evenly between friends and strangers. If you walk in the door with someone you know, make it a goal to NOT sit together.

BARRIER #6: I’m waiting for the other person to make the first move.

Big mistake. You can’t expect someone else to do all the work! Simply waiting for someone else to make the first move and draw you out of your isolation won’t work. This technique is both ineffective and out of your control.

REMEMBER: approachability is a two-way street. It’s both proactive (approach-ER), and reactive (approach-EE). So, concentrate on both stepping out AND welcoming others in.


Think about the last time you went to an event, party or function where you didn’t know many people. Think about the different techniques that other people used to initiate conversations with you. What did you like? What did you not like? This brainstorm is certain to fill your mind with new approach ideas.

BARRIER #7: I was born shy.

Careful. Assumptions like these can actually make you more self-consciousness and hinder your approachability.

Stefan Hofmann, Ph.D., director of the Social Phobia Treatment Program at Boston University explains, “It may be true that people are genetically predisposed to certain characteristics, but the bottom line is that these problems can be controlled, reduced, or even eliminated.”

In other words, just because you were shy at a certain age doesn’t mean you’re stuck with that personality forever. Take Diane Darling, for example. She’s the author of the best-selling book, The Networking Survival Guide. Believe it or not, she was “born shy” too. But, years ago when she started her training company, she vowed to overcome it. So, she studied, researched and practiced the principles of effective communication for years. Now, she leads seminars around the world on conquering shyness!


Nobody has to be shy forever. There are countless resources available to help you overcome it. For starters, just go to Google and type in “overcoming shyness.” About 100,000 pages will come up. That should get you started!

BARRIER #8: I am not as friendly, outgoing and extroverted as that person.

So what? That’s an unrealistic social comparison. After all, you don’t need to be like someone else; you need to be like yourself. And consider this: there are millions of people in the world who are “successfully shy.” These individuals simply change the way they think and act; without changing who they are as a person. In fact, there’s nothing wrong with being shy! That probably means you’re a really good listener.


Self confidence increases the more you give yourself positive messages. Try this: make a list called “Top Ten Things I Like about Myself.” It’s a valuable exercise because many people have difficulty recognizing all their positive attributes because they’re more used to criticism than praise. So, put each of your good qualities on an post-it note and place them on your bathroom mirror. Look at them twice a day while you brush your teeth as a reminder to be supportive of yourself.

BARRIER #9: I can’t just walk up to her – she’s the CEO!

You’re not alone. Authoritarian figures are often perceived as intimidating, both to shy and outgoing people alike.

Notice I said “perceived.”

CONSIDER THIS: have you ever discovered (after approaching someone) that they turned out to be signifcantly more down to earth than you thought? It’s a common misconception. Bosses, managers, CEO’s, presidents, chairpersons, big shots and other head honchos aren’t as untouchable as they once were.

See, we now live and work in a culture that demands authenticity. In 2005, a study from Cornel University surveyed 6,500 hotel employees worldwide. Their research proved that organizations with employees who rated their managers as “authentic,” were “more profitable than companies whose managers had gaps between their words and actions.”

Now, this doesn’t mean that every authoritarian figure will become your new best friend. But more often than not, starting a conversation with one of them isn’t as bad as you think.


When approaching someone in a highly regarded position, remember three things. 1) Have explicit objectives in mind. 2) Respect their time, or lack thereof. 3) Link your goals to that person’s core values.

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