Awkward conversation

How to talk to anyone

Does meeting strangers make you nervous?

Do you have a hard time talking to people you don’t know?

Do you feel like an outsider at networking events?

Maybe you are like me, when I first came to America in 1995, the fear of talking to people used to paralyze me. 

I’d often cross the street just so I didn’t have to talk to someone headed my way.

It took many years for me to realize how important people can be.  

I want to share what I’ve learnt over seventeen years of overcoming this by studying the greats.

These skills became critical to me whether I was starting a new job, interviewing for one, going to a conference, networking or just wanted to make new friends. 

 

TALK ABOUT THEM:

When you meet someone for the first time, hands down the easiest thing you can do is ask them about themselves.

It is never an offensive topic.

People always have something to say about themselves.

One of the tricks is to ask an OPEN question.

A closed question is a question that can be answered in a word or two. For example, you might ask, “How long have you worked here?” The other person can say “5 years,” or shut up. Now the burden is on you to keep the conversation going.

There are many problems with asking closed questions

First, because they can be answered so quickly, you usually have to ask many closed questions to fill the time.

Second, this is exhausting work for you.

Third, a series of closed question is NOT a conversation, it is an INTERROGATION.

Q: How long have you worked at Morgan Stanley?
A: 5 years.

Q: What is your role at Morgan Stanley?
A: I’m a Vice President.

Q: Did you graduate from Wharton?
A: No.

You see how it feels like an interrogation.

The art of having a conversation, especially a conversation where you don’t have to work hard, is to ask OPEN questions — questions that require a verbal “essay” to answer.

For VPs and MDs, I usually ask, “So how did you get started on Wall Street?” I’ve never gotten anything shorter than a 10-minute answer. I’ve even gotten 20-minute answers.

This is a good 80/20 rule-of-thumb for an introvert: Ask one question and get 10-30 minutes of conversation out of it. So think of a few open-ended questions, and then ask them.

 

LISTEN DEEPLY:

You would be surprised how few people actually listen deeply to the other person. Most of the time when the other person is talking, we are putting all of our energy into deciding what we are going to say next.

Too often we’re being polite: we act as though we’re listening, when we’re really just waiting for them to stop talking so we can say whatever we were planning to say (regardless of what the other person just said!).

When you ask an open question, they are going to give you a long and detailed answer. All you have to do then is ACTUALLY LISTEN to what the other person is saying.

Then when you hear something interesting, make a comment about your own experience or ask a more detailed question about that topic.

You could say something like, “Wow. Really? What was that like?”

When you ask an open question, the other person will tell you all kinds of stuff. Then all you have to do is listen deeply, look for something interesting and either comment on that or ask a clarifying question.

I’ve done this with MDs, CEO, Partners, billionaires — pretty much everybody.

The thing is, EVERYBODY is INTERESTING.

Usually most conversations stay at a superficial level, so a lot of the interesting stuff doesn’t come out.

But, if you ask people open questions, listen deeply and show you are interested in hearing more, they will share more and more.

 

TURN OFF YOUR INNER VOICE:

When you’re at a networking or social function, sometimes instead of engaging with other people, you end up having a conversation with your “inner voice.” The conversation with your inner voice sounds something like this:

“I hope nobody notices I’m not talking to anyone. This is not going well.”

“Geez, I wish someone would come up and talk to me.”

“When does this thing end? Is my suit okay? Did I spill something on my shirt? Should I check my mobile phone to look like I’m busy? It’s better than just standing here with nothing to do.”

“Am I loser? No, I am not a loser. Then why do I feel like a loser?”

This is what the inner voice conversation sounds like.

I know this because this is what I used to say to myself at conferences, meetings and networking events — and from time to time still do.

When I was younger, when I was having conversations with other people, I would simultaneously have a conversation with my inner voice. The problem with this approach is I wasn’t able to listen deeply to the other person because I was distracted by also listening to myself.

Invariably, the other person would lose interest in the conversation because they didn’t like competing with the conversation going on in my head.

The solution is to turn off (or at least turn down) the volume on your inner voice, especially when you’re in the middle of a conversation with another person.

Just pay attention to them.

 

PAY ATTENTION TO YOUR BODY LANGUAGE:

Your body will often communicate what you are thinking or feeling. Look out for the signals your sending. Your body language can also impact how you see yourself. Social psychologist Amy Cuddy has done a lot of work to show how “power posing” — standing in a posture of confidence, even when we don’t feel confident — can affect testosterone and cortisol levels in the brain, and might even have an impact on our chances for success. 

I have personally found that a mix of deep breathing, strong postures and smiling can make me feel much more confident than I really am.

As Amy says in the video below (highly recommended), sometimes you have to fake it, until you become it.

GET LOW-STAKES PRACTICE:

If your career path has involved working on your own more than working with other people, consider getting more opportunities to practice your interpersonal skills.

Every little bit of interpersonal interaction helps improve those skills.

If you can, join groups, clubs, meetups or industry associations so you have plenty of opportunities to practice.

If you’re on campus, go to information sessions of firms that aren’t in your top 5 list.

Even interview for jobs you don’t really want (I still do).

The key is to use the skills in an environment where there’s no downside to doing it poorly.

 

GET COMFORTABLE WITH YOURSELF:

It’s my theory that most social awkwardness and anxiety comes from some combination of:

a) being intimidated by the other person and putting them on a pedestal;

b) being secretly afraid the other person will see you and somehow find you lacking; or

c) being uncomfortable with being yourself.

The root cause of these three dynamics is low or diminished self-esteem. One trademark of low self esteem is the presumption that one is somehow inferior to others or, on the flip side, presuming most people are better than you.

 

Another way low self esteem expresses itself is by acting superior to other people. You might notice this as arrogance. When you’re right and have high self esteem, there is no need to convince others you’re right. It’s enough simply to know you are right and they are wrong.

But if you’re right and have low self esteem, the insecurity runs so deep that being right isn’t enough. There’s a need to prove others wrong, to make them see that you’re right and they’re wrong. It is this public perception of superiority that helps this kind of person feel better.

This behavior is a severe over-compensation for low self esteem.

Both of these extremes are enormous obstacles to being comfortable with yourself. The premise of both points of view is that “something is wrong with me.”

To work on this, you have to use self-compassion.

While self-esteem is about telling yourself you are good and worth, self-compassion is not about judgement or evaluation of self-worth.

Its not about deciding whether you are a good or bad person; it’s just about treating yourself kindly.

According to Kristin Neff, a professor at the University of Texas at Austin and the author of Self-Compassion:

When self-esteem deserts us, which is when we fail and we make a mistake, self-compassion steps in. Self-compassion recognizes that it’s natural and normal to fail and to make mistakes, and that we are worthy of kindness even though we’ve done something we regret or didn’t perform as well as we wanted to. 

I’ve found that most of our issues with our people and in the unhappiness we feel comes from being harder on ourselves than others.

It’s this lack of compassion that can makes us afraid, scared and stops us from being ourselves. According to Kristin, the solution to this is to talk to yourself the way you would talk to a friend who was having problems:

One easy way to be self-compassionate is just ask yourself, “What if I had a very close friend who was experiencing the exact same thing that I am experiencing now?” The idea is you use that same quality of warmth, support, encouragement, tenderness, understanding with yourself that you more typically show to other people.

So first, admit your mistakes and faults. Be honest with yourself. Don’t be in denial. Then forgive yourself. Going forward, every time you mess up, forgive yourself, get back up and start again.

For me, it was only when I fully grasped this a few years ago did I finally become comfortable with who I was. Almost instantly after that, my network and how comfortable I felt in a social setting grew.

 

To Sum Up:

Talk about them: Ask open ended questions 

Listen Deeply: Really pay attention to what they are saying

Switch off your inner voice: Stop the inner dialogue, just be present

Watch your Body Language: Watch the signals you are sending

Get Practice: Practice social interaction like any other skill

Care about yourself: Be compassionate with yourself and who you are

 

I hope these quick tips were helpful to you.

Join thousands like you and receive our weekly email with Wall Street wisdom on how to be smarter, richer, happier.

Become a What I Learnt on Wall Street VIP

* indicates required