How to Talk to Strangers and Enjoy It

A few days ago, I was in Manhattan taking a seminar on screenplay writing. During my time there, I had one night where I didn’t have any plans or commitments.

As an experiment, I invited a few dozen CIBs, 1Y, 2Y to a last-minute, impromptu Q&A session in the lobby of my hotel.

(The crowd got so big that we ended up taking over most of the lobby and they kicked us out! My apologies to anyone who came at the end of our scheduled time, as we had by then moved to a conference room. I was hoping 5 people would show up, but when close to 30 did, the hotel kicked us out. Lesson learned.)

During this informal “shop talk,” a 1Y from McK asked me how to be more comfortable meeting strangers (e.g., new clients).

At the time, I gave what ended up being a partial answer. I was planning to send a revised answer to everyone who attended in person.

Instead, I thought I’d provide the full answer here as I actually get asked this question a lot. Usually, the question is asked in the context of networking at information sessions or connecting with people in your network to secure an interview (for lateral hires, non-target school hires, etc.…)

Before I provide several mindset shifts and techniques that I’ve found helpful, it’s useful to understand something fundamental about the strategy consulting industry.

The type of people who have the analytical skills to do consulting, tend to be introverted and unaccustomed to being around other people constantly in their work lives.

(If I had to guess, I’d say that at McKinsey 65%–75% of the consulting staff were introverts—albeit introverts with at least functional people skills. The remainder were extroverts with strong analytical skills. I’m oversimplifying here, but hopefully, you get the idea.)

So, here are some short, medium, and long-term solutions for how to improve your people skills—in particular, the ability to meet new people for the first time, and maybe even enjoy it.

SHORT-TERM

1) GET THEM TALKING ABOUT THEMSELVES. When you meet someone for the first time, hands down the easiest thing you can do is ask them about themselves.

This is a very popular topic!

It is never an offensive topic. People always have something to say about themselves.

One of the tricks is to ask an OPEN-ENDED question.

A close-ended 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 “2 years” or shut up. Now the burden is on you to keep the conversation going.

There are many problems with asking close-ended questions.

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

Second, this is exhausting work for you.

Third, a series of close-ended questions is NOT a conversation, it is an INTERROGATION.

Q: How long have you worked here?
A: 2 years

Q: What is your role at McKinsey?
A: I’m an engagement manager

Q: Did you graduate from XYZ school too?
A: No

Q: Do you know what the campus recruiting schedule is for this year?
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-ENDED questions—questions that require a verbal “essay” to answer.

For CEOs, I usually ask, “So how did you get started in XYZ field?” I’ve never gotten anything shorter than a 10-minute answer. I’ve even gotten 30-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.

When I used to do informational interviews for networking purposes, I’d ask the same question. When I was in college, I asked a famous venture capitalist that question at his desk and spent 45 minutes listening to the answer. I’ve asked senior executives at Wells Fargo and several investment bankers that same question. They all talk about it for 10–15 minutes or more.

It is a good question. So, think of a few open-ended questions, and then ask them.

2) 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-ended 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?”

For example, I once had a lunch meeting with a prospective client—an owner of a small business, a market leader in a tiny niche. Our one-hour scheduled lunch turned into a FOUR-hour conversation. It was just an interesting conversation.

I guess we started sharing more personal details (which tends to happen if you are being a good listener) during the conversation. I had mentioned that there was a brief period in my entrepreneurial career where I was selling a product I wasn’t proud of and was actually embarrassed to be associated with it, and it really sucked my soul dry.

I was explaining how it was a mistake, but I learned a lot from it. It’s also the reason why I now never attach my name to something unless it’s an exceptional product or service.

Well, I think I struck a chord at this point, because she said, “I know exactly how you feel. I used to be a stripper in Las Vegas.”

(I SO did not expect that comment!)

So, what did I say?

Yup…

“Wow. Really? What was THAT like?”

And then off she went for another 20 minutes.

You see, when you ask an open-ended 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 bus drivers, waitresses, CEOs, parents—pretty much anybody.

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-ended questions, listen deeply and show you are interested in hearing more, they will share more and more.

Also, this kind of interaction very much feels like a conversation.

If you show more interest in someone, they will often take a deeper interest in you. It’s a natural human instinct to reciprocate, so the more you hear them out, the more they want to hear you out. The “secret” is to hear them out FIRST.

3) TURN OFF THE 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 hair 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.”

“Oh shoot, my drink is almost all gone. Maybe I should get another. But I don’t actually want one. But what do I do with my hands? I need to do something. I can’t just stand here.”

“Am I a 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 cocktail parties, information sessions, 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.

4) ASSUME THE OTHER PERSON IS MORE NERVOUS THAN YOU. The majority of people I know feel at least a little awkward meeting new people (though some people are better at hiding it than others). Most people also tend to assume that everyone else is more socially comfortable than they are.

So, what happens is, you have all these people standing in a room. And instead of talking to each other, they talk to themselves inside their own heads.

This ends up becoming a self-reinforcing cycle.

The way to break this cycle is to assume everyone else is more nervous or feels more awkward than you.

Then make it your job to help others feel comfortable by reaching out and engaging them. Even if they are not great conversationalists, that’s okay. Just ask them about themselves!

Then listen deeply, keep your inner voice quiet, and they will respond to you.

MEDIUM-TERM

5) GET MORE 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.

The main reason my people skills were functional when I was recruiting was because I happened to do a number of extracurricular activities in high school and college that involved working with other people.

I also took two different sales jobs while in school: one selling Yellow Pages advertising face-to-face, and the other making cold calls for Merrill Lynch. At best, I was pretty mediocre at both of those jobs despite working really hard at them.

Every little bit of interpersonal interaction helps improve those skills. If you can, join groups, clubs, meetups, Toastmasters 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 10 list. Then go practice interacting with the people there.

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

LONG-TERM

6) BECOME COMFORTABLE WITH YOURSELF. It’s my theory that most social awkwardness and anxiety comes from some combination of:

1. a) being intimidated by the other person and putting them on a pedestal;
2. b) being secretly afraid the other person will see you and somehow find you lacking; or
3. 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.

(The problem, of course, is that this comes at the expenses of others feeling worse about themselves, which makes them unwilling to work with or be near you)

This behavior is a severe over-compensation for low self-esteem. Basically, these kinds of people don’t feel good about themselves and don’t want anyone to discover this “fact”, so they act arrogant and cocky, with a lot of (false) bravado to hide their insecurity.

People who overcompensate by conveying superiority are people who place themselves in a “one-up” position.

And when someone tends to automatically assume they are in some way “less than” other people, that’s a person who places himself in a “one-down” position.

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.”

The one-down person tries to “hide,” hoping nobody will notice and see these self-perceived flaws. The one-up person tries to act bigger than they are and hide behind a mask of superiority.

In the general population, I’d say 75% of people are either one-up or one-down. Within McKinsey, it’s a fairly open secret that 80%+ of McK consultants are one-down-type people—myself included.

Here’s why.

While there are many ways one-down people cope (e.g., addictions, self-medicating, abusing others), one of the more socially acceptable ways is to be addicted to work and, as a byproduct, achieve extraordinary career success.

There’s nothing wrong with hard work unless you’re doing it is an addiction because not working (and therefore saying something about you and your worth) scares you to death.

This is not to say everyone who is successful is doing it for these reasons.

But among this group, in which I include myself, the implicit rationale is, “If I just get X (an MBB offer, a Harvard degree, a 2nd Harvard degree, a CEO position, etc…) then everyone will congratulate me, treat me like I’m special, and I’ll feel better about myself.”

(I hate to be the bearer of bad news, but it doesn’t work. There’s a temporary high from a new career achievement, but it fades within a few months. I know this because it describes most of my life. More on this later.)

Even if you are not a one-up or one-down person, I believe there’s a 100% chance this dynamic impacts the people that you interact with every day, including clients, co-workers, family members, and friends.

If you want to develop exceptional people skills, you absolutely, positively have to understand how this dynamic works.

You need to learn to recognize it in yourself, recognize it in others, and know how to work with yourself and others, given their tendencies.

For example, if you have a client that has a tendency to go “one-up,” he will often resist any idea that’s not his own. If you’ve been in the corporate environment, particularly in the US, you may have heard of the acronym: NIH (Not Invented Here).

A one-up person does not like any ideas that were Not Invented Here.

The key to winning over a one-up client is to let your idea be his idea. He is not threatened by “his” ideas. But he is threatened by an outside idea (that he did not think of himself), especially if it’s a good idea. It is perceived as proof that he wasn’t adequate for the task at hand.

By the way, one-up people are not inherently bad. One of my very good friends from high school went “one-up” all the time. All it says is he’s just afraid people will think he’s not good enough. It’s a fear reaction.

When you understand the humanity behind such outwardly aggressive behavior, you learn to feel compassion for the other person. They will detect this and allow you to develop a closer relationship with them because somehow you “get” them.

Once you understand the psychology of the people around you, you begin to handle things differently. The above example is just one of dozens of scenarios that you’d handle differently once you understand people better.

This is a very big topic that’s impossible to cover in a single article. While I have a deep personal interest in this topic, I recognize not everyone else does.

If you’d like to learn more about concepts, ideas and tools for dealing with what I call “being human” problems, just fill out the form below: