I've spent most of my adult life working hard to overcome many levels of social awkwardness, from the very basics of having enough courage to talk and knowing what to say to start a conversation to understanding how to read people. From the vantage point of today, I now see how this social awkwardness has cost me in the past, causing me to lose out on promotions, lose out on at least one amazing opportunity with a startup, and fail to take advantage of at least a few opportunities to really wow a room full of people with a presentation.
Let's face it - I'm a strong introvert and the nuances of making friends, communicating well with others, and speaking to others is sometimes a challenge for me. Over the last several years, I've found a number of ways to overcome this problem. Most of these require significant practice, but the truth is that you can practice almost all of these any time that you want. If you're socially awkward at all - and you probably know it if you are - just give some of these exercises a try.
Where did I learn these exercises? These came from countless books on public speaking and human relations. Of my more recent readings, I particularly recommend How To Win Friends And Influence People (read my detailed review) and Never Eat Alone (read my detailed review); both were chock full of useful tips for an introverted fellow like me.
So let's get started.
1. Smile at everyone you meet
To me, this was the trick that really started to break things open. I would often meet people and have no clue how to react, so I would just stand there quietly with a blank face and not say much initially. What I later found out is that most people wrote me off pretty quickly and that I had to actually make up significant ground through other actions in order to give them an overall positive impression of me. The technique that works best for me is thinking about what really makes me happiest, and that's playing with my son - I imagine doing something completely playful with him and that brings out a smile every time. Practice by smiling at people in public places, particularly if you have a brush with them - you're going near them in the same aisle at the store, or you happen to make eye contact with them. Here's an extensive guide to smiling.
2. Practice conversing with people you don't know
I used to just clam up in an unfamiliar environment, but what I've found is that if you make polite conversation with people at every opportunity, it becomes much easier to open up and converse. Any situation you're in where you're surrounded by people you don't know at all or don't know well - a conference, a trip on the bus, a line at the coffee shop, or your spouse's extended family reunion, to name a few - can be used to practice conversation. Take advantage of these opportunities and strike up a conversation with someone who appears idle. Even if you completely bungle it, the worst thing that happens is that you sit back, think about how you bungled it, and move on from there. Many of the remaining tips are advice on how to make a conversation like this go well.
3. When you talk to someone, look them directly in the eye
This was another trait that was difficult for me to master - I tend to want to look away from people, mostly because my mother pounded into my head over and over again that it's impolite to stare, so I kept reducing it to the point where I didn't even want to look at other people. This conclusion is patently ridiculous - when someone else is speaking or when you're speaking to one specific person, you should look them directly in the eye. It indicates interest in the other person, while looking away without a clear purpose often indicates boredom and disinterest. Again, this is easy to practice whenever you have a chance to try conversing with others.
4. Memorize names, faces, and information - memorize people
I find it very useful to find online pictures of people that I will potentially have contact with in order to see their face and associate it with their name. It comes up useful time and time again - if you can come up with someone's name in an initial introduction or in a second meeting, you've gone a long way to make them feel good about themselves as well as about you. Before conferences or other meetings where I'm going to actually have to remember a lot of names and faces, I actually have made what amounts to flashcards so that I can recall quickly who's who based on face alone, recalling their name and a key thing or two about them.
5. When you're about to have a meal, invite someone to eat with you
Meals are almost always a way to disarm people and make conversation easier. Whenever you're thinking of dining alone, make it a point to try to dine with someone else, even if it's just a friend. If I'm at a conference, for example, I never ever allow myself to eat a meal alone - there's always someone worth talking to, even if it's just someone I happened to meet during the normal course of the day.
6. Ask questions
If you don't know what to talk about, think of the first (polite) thing you'd like to know about the person you're talking with and ask. What are their hobbies? What do they think about a particular article they're reading? Do they have any kids? This is particularly easy if you're at a meeting, because you generally have the topic of the meeting in common, as well as the meeting itself.
7. Practice shaking hands
Having a bad handshake is a no-no - you don't want to have a limp handshake, nor a "death grip" one (the latter used to be my problem). I found that the best way to practice this was to simply ask a few close friends for help and shake their hands several times. It was one of my friends that informed me that I had a death grip shake, which I didn't even realize but came to know later that others also thought it was extremely aggressive and that it sent awkward signals (think about it - I would shake with a death grip, look away from people, and not talk). Know how to shake with an appropriate firmness and be sure to do it when you meet someone, particularly in a professional situation (though local customs may frown on handshaking, it is universally appropriate in the United States).