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How to Be the Most Interesting Person in the Room (and Connect with Almost Anyone)

Being interesting is a choice, and it starts by following these 9 tips to connect with almost anyone.

I recently had the great privilege and opportunity to sit down with one of Silicon Valley’s industry giants: Silicon Valley Bank’s Head of Technology Banking, John China (@JohnChinaSVB).

John’s a living testament to the power of relationships. He’s built his impressive career by consistently investing into and leveraging the power of his network, and he’s one of the few who could truly stand next to Tony Robbins in his ability to motivate, uplift, and inspire people through vision and story alone.

But if you were to ask John about his biggest weakness, he’d be the first to tell you that although he’s great at sharing stories that tell people what to do, he often struggles to explain how to do it.

That’s why he and I work so well together: Actionable advice and pragmatism are Mindmaven cornerstones. So as John shared inspiring stories over the course of our conversation, I converted those stories into tactical advice that teach people how to execute on the principles that made John so successful.

The result of this meeting is the blog post below, focused on how to generate breakthrough opportunities by turning the most important people in your network into vocal advocates for you and your business.

I hope you’ll enjoy the depth of John’s real-life stories as much as I do, and it’s my wish that my advice will help you take John’s visions and turn them into reality.

How to Become the Most Interesting Person in the Room 

For John’s first story, we need to rewind a few years. He was in college and his roommate—we’ll call him Alex—was in a serious relationship; so serious he’d been invited over to meet this girl’s family.

But for some reason, Alex wanted John to come along. “I can’t do this without you,” he’d said, so John agreed and the three of them went over for dinner a short time later.

Shortly into the evening, John learned the father had built and sold a software company; something John thought was an impressive feat. So he spent the rest of the evening asking questions to learn about the parents’ life, business, values, and points of view.

They were incredibly open and willing to share, so the conversation quickly got deeper and more meaningful. By the end, John really felt like he’d learned a lot. But after dinner, they all went their separate ways and John didn’t give the evening much more thought. Then, a few days later, Alex’s girlfriend approached John and said, “John, my parents really loved you.”

He was flattered but didn’t get the point she was trying to make. “No, you don’t understand,” she said, “They loved you. Not Alex.” She went on to explain, “They said … your genuine interest in others makes you interesting.

This is a lesson John never forgot.

Mindmaven Pragmatics #1: Be Interesting by Taking an Interest in Others 

When you take a genuine interest in othersthey take a genuine interest in you

But the key word here is “genuine.” You’ve got to ask questions you’re truly curious about; ones you actually care about the answer to. And being genuinely curious is a choice. You can choose to think, “I really want to know about …” By thinking that, you create an authentic desire to learn.

When you ask genuine questions, two things happen:

  1. People start talking about themselves, something most people enjoy doing, and
  2. The more interested you are in the answer, the more intently you’ll listen. And the more intently you listen, the more engaged and caring the other person will perceive you as (more on this later).

Those two benefits combine to create an incredibly positive experience for your conversation partner and, as a result, their memory of you will be as a “very interesting person;” even if all you did the entire time was ask questions.

Mindmaven Pragmatics #2: Send Questions in Pairs 

Speaking of questions as a plural: 

Never fire off a question alone; questions should always be asked in pairs.

The first question usually results in a surface-level answer, because you’re just warming them up to the topic. For example: What was the hardest part about selling your business?

But asking a second question—or what I call firing off the Second Dart—allows you to dig a little deeper. Here are some examples of strong Second Dart questions:

  • What makes you say that?
  • Why is that important to you?
  • What’s your favorite thing about that?

The more questions you ask, the more you allow the other person to talk. And the more you let the other person talk, the more likely they are to remember the interaction as relevant, valuable and meaningful; all attributes they will likely also associate to you.

Seek Those Difficult, Uncomfortable Conversations 

In John’s experience, many people run away from difficult conversations; yet those are the very conversations that allow you to stand out; to deliver above-and-beyond what’s expected.

As a banker, John works with a lot of entrepreneurs, and doesn’t always see them on their best days. He explained: “When I see an entrepreneur in a heightened place of stress—a state I may be partially responsible for—I don’t shy away from it. I view it as an opportunity.”

For example, he told me about a recent meeting he had with an entrepreneur who was in a really tight spot financially and wasn’t meeting his board’s expectations.

After a hard heart-to-heart conversation, one in which John made clear that things might not work out well, the entrepreneur turned to him and said,

“You know, I think when all of this is over you and I are going to be very close friends.

“You changed your entire schedule to meet with me on my terms in less than 24 hours. You’re asking me questions to help me determine how I can turn this around. And you’re telling me very honestly that you’re going to try to help, but can’t promise anything.

“Honestly, no one else is doing that for me, and I want you to know that this is all an entrepreneur could want from their banker: Someone who understands.

Mindmaven Pragmatics #3: How to Have Hard Conversations 

Hard conversations are a part of life, and just because you can avoid them doesn’t mean you should

By being the person that leans in when everyone else turns away, you earn a reputation as someone solid; someone with a strong backbone. 

This, in turn, will cause you to be perceived by others as someone trustworthy and reliable; someone that cares.

Here are three quick tips to make those hard conversations a little easier:

  1. Don’t put off the inevitable. When you recognize the need for a hard conversation, have it as soon as possible. Your responsiveness and willingness to step up sends a clear message to others that you truly care.
  2. Ask questions. Don’t assume you know how the other person thinks or feels, and don’t assume you know what they should do. Always ask ample questions to make sure you truly understand their perspective and situation.
  3. Be authentic. It’s often tempting to over-promise to make the other person feel better. Don’t. If they’re in a hard time, you owe them honesty: Even if that means setting expectations that may not deliver the outcome they’d like.

If you do these three things, there’s a good chance this conversation will create a much deeper relationship with the other person. And if they don’t react well, that’s on them; not you. You can walk away confident, knowing you did all you could.

Any Point of View is Better Than No Point of View 

When it comes to being interesting and making an impact on the people you meet, John stresses the importance of having a point of view:

“It doesn’t matter what you believe, as long as you believe something.”

For example, take a look at the two statements below:

  • “I don’t know what’s going to happen with autonomous vehicles,” and
  • “I think mainstream autonomous vehicles are still many, many years out.”

The first statement is indifferent: It demonstrates someone who doesn’t have a point of view. It’s also an example of a statement that’s likely to end a conversation, simply because there’s nowhere to go from there.

The second statement, while more opinion than fact, at least stands for something, and it invites conversation; even if the person you’re talking to disagrees with the statement. For example:

You: “I think mainstream autonomous vehicles are still many, many years out.”

Them: “Really? That’s interesting, because I believe we’ll start seeing them on the road in the next three years or so. I hear Waymo is planning to bring a fleet of them to Phoenix in the near future.”

You: “That’s true. What else have you seen that makes you feel that way? I’d love to see autonomous cars sooner rather than later. But based on Uber’s difficulties, I think the challenges are a lot further away from being resolved than others might think.”

Someone doesn’t have to agree with your point of view to find it interesting. The trick, John says, is that your point of view—whatever it is—must be informed.

In the example above, both beliefs were backed by industry knowledge, but that’s not your only option. You can also back your beliefs with life experience. To illustrate this, John told me about a VC dinner he attended shortly after his wife’s uncle had passed away.

He passed with a Do Not Resuscitate order, and John wasn’t sure how he felt about the practice. He was still mulling it over when he attended a VC dinner.

During a lull, John shared the story, then followed it up by saying, “I’m curious: What are your views around DNR orders?”

This simple question ended up sparking an interesting conversation that helped John process his own thoughts and feelings. And while by the end of the evening not everyone agreed, everyone had contributed.

John clarified that you don’t have to be as outgoing as him to have these conversations. They don’t require deep skill or even expansive knowledge.

All you need to do is make a choice, then speak up.

Mindmaven Pragmatics #4: Be Intentional About Your Points of View 

The fact of the matter is, as a human being, you probably already have enough knowledge or experience around topics that interest you to develop a point of view. You just need to own it.

So identify 3-5 topics you’re already passionate and knowledgeable about. It’s important that you have a genuine interest in the topics you choose; if you don’t truly care about the topic, that’ll come across in the conversation.

So pick topics you care about, then choose your stance. Once you know what you believe and why you believe it, you can enter practically any room or networking event confident that at least one of your perspectives will lead to an interesting conversation.

Mindmaven Pragmatics #5: Overcome Limiting Thought Patterns 

One of the common reasons people avoid sharing their perspectives is fear. They tell themselves, “No one cares what I think,” or, “What if they do care, and they disagree? That could destroy this relationship!”

And while those thoughts are natural and understandable, they’re holding you back from leveraging one of your most powerful conversational assets: Your beliefs.

And all without good reason, because the truth is, most of your fears are probably unfounded. Many of us have a tendency to overestimate how others will react to our points of view. In most cases, there won’t be any negative consequences; and if there are, they’ll be minimal.

At the end of the day, any viewpoint–even if it’s on the opposite spectrum from the your conversation partner’s beliefs–will still make you more interesting than if you were to say nothing at all.

Note: There are exceptions to the “any perspective is better than none” rule. Generally speaking, try to steer clear of emotionally-charged topics like religious or political extremism. 

Mindmaven Pragmatics #6: Find the Right Topic for Each Conversation 

Once you’ve identified your 3-5 core points of view and overcome any limiting beliefs around them, you’re ready to start bringing them up in conversation.

This probably goes without saying but, in most cases, you don’t just want to walk up to someone and spew your perspective, like, “It is my belief that autonomous cars will be introduced to the public within the next three years.”

First off, it’s an unnatural start to the conversation. Secondly, you don’t even know if the other person has any interest in autonomous cars; and for them to perceive the conversation (and, by extension, you) as relevant and interesting, they must have some interest in the topic. 

You can explore which of your perspectives would be most relevant to the other person by utilizing the first skill we talked about: Asking questions. For example: “I just read that Waymo is looking for test “drivers” for their fleet of autonomous cars. Are you as intrigued as I am by the development of autonomous cars?”

  • If they say yes, you could respond with, “Me too. I’d love to hear your thoughts: Are you also intrigued by the development of autonomous cars?”
  • If they say no, you could redirect the conversation by saying, “Alright, I’m curious: What are you passionate about?”

In short: If they seem to have an interest in the topic, great! Continue it and, whenever it feels natural, you can introduce your perspectives. If they don’t seem to have an interest, use questions to move the conversation toward one of your other perspectives.

Note: You can shortcut this process by performing Icebreaker Research prior to meeting someone. This will allow you to find common ground in advance or, if there isn’t any, to develop a point of view around whatever they’re most passionate about. 

You Can’t “Hack” Experience and Skill 

If you want to leverage your network, develop breakthrough opportunities, and turn your contacts into advocates for you and your business, you need one thing above all else: To be really good at what you do. 

All the relationship and opportunity generation hacks in the world won’t mean a thing if you yourself aren’t worth referring.

At the end of the day, the most important thing is that you know your stuff; this was a lesson John learned the hard way:

Early in his career, he tried to cut corners and didn’t quite understand how everything worked. One day, he found himself in a conversation with an experienced entrepreneur, and the topic of conversation quickly exceeded John’s knowledge.

He tried to pretend he knew what he was talking about but, no surprise, it didn’t work. The entrepreneur just shook his head and walked away; and John never got another chance with him.

As a professional, there’s no way around it: You must know your trade inside and out. 

If you want to play at the top table, you need to understand the game; otherwise you’ll almost always be trumped by the person who does.

Mindmaven Pragmatics #7: Create Quarterly Learning Goals 

No matter how much you know today, there’s always more to learn. That means constantly investing in learning.

Once a quarter, I recommend choosing one aspect of your industry you feel you don’t understand well enough, then setting out to master it.

Once you’ve decided what you want to learn, write it down in the form of a question and schedule it as a calendar event three months out. For example: “Did I invest the time to learn startup capitalization this quarter?”

The simple act of setting the intention by scheduling something often dramatically increases the likelihood that it’ll get done.

Note: Feel like you don’t have the time to invest in learning? You just need a new approach to time management. Check out Whitespace Time Management: The Proactive Entrepreneur’s Guide to Owning Your Time and Mastering Your Priorities.

Stop Talking, Start Listening 

Talking’s easy. Anyone can do it. Listening? That’s hard. Most people hear a conversation, but few people actually listen.

In John’s experience, this is especially true in high-pressure environments: People get nervous, and those nerves cause them to talk. The result is usually a bunch of empty, meaningless conversations that contributed nothing to anyone.

So it isn’t enough just to ask questions, you must actively listen as the other person speaks. Because … 

Only through listening can you truly understand someone, and only through understanding someone can you provide them maximum value.

Mindmaven Pragmatics #8: Develop a Listening Mindset and Awareness 

Listening is a skill many of us take for granted. As a result, few people do it well. But if you can deliver the experience of being truly heard to someone, you’re going to leave a very strong, very positive impression.

So what stops us from listening? As John pointed out above, a lot of the times it’s nerves; but not always. Here are a few other things that often get in the way of active listening:

  • Assumptions: When you assume the other person has nothing interesting to say, you signal to your brain that it’s okay to tune out.
  • Distractions: If there’s something else on your mind or someplace else you’d rather be, it’ll be clear you’re not fully present in the conversation.
  • Rehearsals: Too often, people are so caught up in rehearsing what they’re going to say next in order to make a good impression that they fail to truly listen.

These are bad habits that need to be overcome before you can fully engage in active listening. The easiest way to break that habit is to regularly ask yourself in conversations, “Am I really listening to this person?”

At first, the answer is probably going to be “No” more often than not; but simply having that awareness creates the opportunity to make a change.

The Secret to Mastering These Principles 

By his own admission, the stories and strategies above have played an integral part in John’s success; but there’s one key trait you must possess in order to fully leverage the power of these tactics:

Willfulness.

For most of us, the concepts above don’t come naturally; if they did, we’d already be doing them. So in order to adopt them and turn them into habits like John did, you must genuinely want to do them.

  • You must want to ask questions.
  • You must want to listen.
  • You must want to be the best.

Unless you have the desire, you won’t have the follow-through; and without the follow-through, you won’t have the results you’re looking for.

Mindmaven Pragmatics #9: Create Your Own Identity 

Let me leave you with one final tip: You have the power to be whoever you want to be.

It’s often tempting to look at others and say, “I just don’t have what it takes. Look at Tom over there: He’s just naturally likeable and outgoing. His personality allows him to do all of this, but mine doesn’t. I’m an introvert.”

The skills above are not exclusive to extroverts. In fact, I’d argue some of them—such as listening or asking questions—even favorintroverts. But at the end of the day, it’s not about your natural inclination. It’s not about your responsibilities. It’s not about your role.

It’s about defining the identity of the person you want to become, and choosing that identity every day. 

If you decided with absolute certainty that you wanted to compete in Iron Man competitions–and turned that identity into a “must, rather than a “should” or “could”–you would become that identity.

In the same way, you can make the decision to be the person who is perceived as interesting, insightful, likeable, knowledgeable, and–most importantly–someone who cares.

If you think being this type of person would give you a sense of fulfillment and satisfaction, then don’t wait. Commit to being the type of person you want to be.

So here’s your chance. Make your choice: Who are you going to be from here on out?

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