The Definitive Guide to Asking Questions, Part 1

This is the sixth article inThings You Don’t Talk About at the Dinner Table“, a series about how to create an environment of trust and openness, where anything can be discussed.

One thing that I’ve seen lots of confusion about regarding connection is questions and their relationship to connection.  On one hand, you have people who think that asking questions shows weakeness and stops you from “offering value” to the interaction.  On the other hand you have people who think asking questions are the end all and be all of connection, and they’ll ask questions till the person they’re with is blue in the face.

The truth is, just like most things in interpersonal interactions, there are good questions and  bad questions, and good times and bad times to be asking questions.  For the purposes of connection, I have a very simple definition of what defines a good question:

A good question is a question that lets someone else talk about what they want to talk about, and let’s you hear something you want to hear about.

That’s it.  Anything else for our purposes is considered a bad question.  Any question that fulfills those simple criteria will enhance connection, 99% of questions that don’t fulfill that criteria will hurt connection (the exceptions will be discussed in a later article about enforcing standards).

So there are two aspects you have to worry about when asking questions.  The first part is “Am I really interested in the answer?”.  If the answer is no, you’ll want to learn how to develop a sincere interest in other people.  The second part is “Does the other person want to talk about the answer?”.  To figure out what other people want to talk about, read on.

What Do Other People Want to Talk About?

Figuring out what other people want to talk about is another challenge entirely, it involves some amount of trial and error, casting around a bit until you hit upon a topic that makes the other person happy to be talking.  What you can do is greatly increase your chances by focusing on a topic that is universally important to human beings:  themselves.  The trick is to find an aspect of them that THEY consider important.  I’ll list a number of possible topics below.  If you can think of any more, let me know and I’ll add them to the list.

1.Their Passions

2.Their Worldviews

3.Their Future

4.What’s On Their Mind

5.Their (Happy) Memories

That list is just a short list to get you started.  Anything that people like to think about, they’ll usually like to talk about as well.  The trick is showing that you’re genuinely interested in what they’re saying, and letting them feel safe enough to talk about it.  Next week, I’ll talk about conversational tools you can use to better hone in on the right questions.

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The Myth of Compatibility

This is the fifth article in “Things You Don’t Talk About at the Dinner Table“, a series about how to create an environment of trust an openness, where anything can be discussed.

Today I want to take some time to dispel a number of common yet harmful mindsets around the issue of creating and maintaining relationships.    They all center around this issue of what I call the myth of compatibility.

The myth of compatibility in a nutshell, is this:

Some people are meant to connect with each other, and some aren’t.

From this erroneous belief, stem other harmful and false mindsets, which hurt your ability to connect with others. First, that connecting with others should be effortless and simple, and second, that superficial commonalities determine the success of a relationship.

The Myths of Compatibility

Myth 1: Connection Should Be Effortless

This myth was brought to my attention in a comment on one of my other articles about how to create relationships.  The gist of the comment was that because the article talked about how to CREATE connection, it was automatically a bad idea, because connection should not have to be created.

While I see where the commenter is coming from, I categorically disagree with the sentiment.  In every worthwhile relationship I’ve had, there’s always been a point where the relationship becomes strained, and it takes some work to rebuild the connection. I would venture a guess that if you look at your own relationships, you’ll discover a similar situation.  Wouldn’t it be silly to discount a relationship, just because this period of lower connection comes at the beginning of the relationship instead of at the middle?

Reality: Relationships are hard work.

Myth 2:  We Have Nothing in Common

This is a common one I see.  There’s actually two beliefs that bring this statement about, both of them false.  The first erroneous belief is that it’s actually possible to have nothing in common with another human being.  The truth is, you have more in common with any given person than you have differences with them (The Second Formulation of the Law of Average Joes).

We can start with the most obvious way to disprove this: Do you both have two eyes, a nose, and a mouth?  On the most basic level, you’re both human.  But honestly, that’s a pretty stupid argument, who connects on aspects of their anatomy?

What I’m going to argue is much deeper.  I’m going to argue that deep down, in all of us, there’s a basic human goodness.  There’s an inherent value deep inside our being, which is common to every human being on the planet. It’s THAT commonality that you can connect on, and that’s why I think you always have something in common with another person.

Reality: Everyone has a deep inherent value in common with everyone else.


There’s also another myth hidden in this statement, and that’s the idea that you must have something in common with somebody else in order to connect with them.

However, have you ever met someone who had such different beliefs from your own that you were immediately fascinated by them?  Ever had the experience of trading differing beliefs with somebody, and feeling closer to them because of it? You didn’t connect on commonalities, you connected on differences. (I also talk about this briefly in my article about how to begin to create relationships.)

Reality: You can connect on differences just as easily as commonalities.

The Reality of Relationships

The misconceptions above, and the idea of compatibility itself all stem from a fundamentally flawed mindset.  It’s a mindset which says that relationships are something which happen TO you, a mindset of reaction.  I want you to consider coming from a more proactive mindset.  Love, trust, connection, understanding, these are not things which you simply HAVE, they’re things which you must DO, ways that you must BE. Instead  of whining that there’s no trust in a relationship, BE more trusting.  Instead of complaining about not understanding someone else, BE more understanding.

With hard work on yourself and a relationship, I believe that you truly can connect with anybody.  Hopefully I’ve convinced you that compatibility is a myth… the rest is up to you.

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One Rule That Creates Rock Solid Relationships

This is the Fourth Article in “Things You Don’t Talk About at the Dinner Table“, A series about how to create an environment of trust an openness, Where Anything Can Be Discussed.

In the entrepreneurship program at my school, it seems I run into a new student entrepreneur every day.  These are people that I definitely want to know.  In addition to being great contacts to have in the future, they’re exactly the type of action oriented high achiever types that I love to talk to.  I’ve tested out a dozen different conversation starters and icebreakers to meet them, but only one have I found to consistently work:

“I checked out your website, it was really cool”

Perhaps the most important part of developing a climate of trust, even more important than how you interact with someone, is your relationship with them.  I’ve found very few rules that consistently work for developing relationships, but I have found a few, and one that I have found more useful than any other in creating relationships.  The rule is this:

Develop a Sincere Interest in Other People.

It’s simple, but highly effective.  Like I alluded to above, one of the best conversation starters is to mention something about the other person that you find interesting.  In the example above, I was interested in what they were doing.  However, there will be circumstances where you’ll simply have different interests than the other person.  The question remains, how do you become interested in people you have nothing in common with?

4 Ways to Become Interested in People You Have Nothing in Common With

So if you can’t be interested in what someone else is doing, how can you be interested in them?  The trick is to find some aspect of their interest that’s interesting to you.  This allows you to connect with people that you have absolutely nothing in common with.

1.Be Interested in Their Passion

When I was in elementary school, I knew a guy who’s life ambition was to be a truckdriver.  I wasn’t really interested in driving trucks myself, but his passion was something I could definitely connect with.  You can use the same tactic, to connect with someone on any topic they’re passionate about.

2.Be Interested in Their Process

I have a friend who paints.  Now, I’m not really much of an art enthusiast.  I don’t care much for paintings, they’re just not interesting to me.  However, what I do find fascinating about my friend is her process, how she comes up with ideas, begins to paint, visualizes the result beforehand, etc.  By becoming interested in her process, I can find out more about her interests, even if they’re not the same as mine.

3.Be Interested in Their Interest

I’ve never liked history.  I never saw any practical application for it, and the rote memorization of dates wass just never my thing.  However, I have a number of friends who are super interested in history.  I’ve had several conversations with them about history, and instead of falling asleep, I’ve always been super engaged.  The reason is that trying to figure out how and why they like history is interesting to me.  How can they like something which to me seems so obviously boring?  This interest in HOW they’re interested allows you to connect on topics which you would normally be bored to tears by.

4.Be Interested in Them

My sister is out in LA right now making movies.   Now, I do find the process of making movies interesting, but it’s not normally something I would choose to spend my time discussing or finding out about.  However, when I’m talking with my sister, I find it the most fascinating thing in the world.  Why? Because it’s her that’s making the movies.  If you find the person interesting, then be interested in what they’re doing simply because they’re doing it.

Using these techniques, you can begin to create rock solid relationships, even with people you have nothing in common with.  Use them wisely.

Click Here to Read the Rest of this Series.

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