The Simplest Way to Becoming an Interesting Person

Boredom occurs when you fail to make the other person interesting.

Warren Bennis

Of all the communication skills workshops I give, my favorite focuses on How To Talk To Anyone.

I again offered this workshop last week and I began by asking the participants, “Who do you enjoy talking with?” Folks quickly responded with some version of, “I enjoy talking with interesting people.”

When I asked what makes someone “interesting” they offered a variety of answers including: well-traveled, educated, athletic, musical, artistic, etc. I pointed out that while those traits and abilities have the potential for making someone interesting, I’ve met MANY well-educated, traveled, talented people who I found boring and/or obnoxious. They simply laughed – in agreement.

Sure, we all enjoy talking with people whose life experiences are different from our own BUT what really makes someone interesting – for all the right reasons?

Here’s what makes someone interesting to me –

confidence + healthy self-esteem + competency + a keen interest in the “other”

A confidently competent person is of little value if they are not genuinely interested in the person(s) they are dealing with.

Simply put, an interesting person knows how to make the other person feel recognized and valued.

When I asked the participants if they considered their own self to be “interesting” most said “NO” or at best only half-heartedly thought they were interesting.

Jacob said he thought he wasn’t “enough” and so wasn’t interesting. He admitted no one has ever directly accused him of being boring or of not being “enough” BUT he knows that he’s not enough.

So, true confession, there was a time when I thought I was boring and not enough. I was heading off to college and didn’t know what to do in order to stop “being” boring.  Before I walked through the campus gates of Fordham University, I decided to be bold in reaching out to people who scared me.

Who scared me? The people who scared me were the people who I thought were living life.

I joined the college radio station (WFUV) and I interviewed all sorts of writers and artistic types hoping they’d give me some glimpse into what it was like to live an interesting life. The most interesting of these people was famed diarist Anais Nin.

With my trusty tape recorder in hand, I went to her Greenwich Village apartment to interview her. I remember how gracious she was when she waved me into her living room. She served tea and then, just as I had set up the recorder, she abruptly said, “Wait!”

She stood up, went over to phone jack and unplugged the phone. She smiled and said, “I don’t want anyone to disturb us.”

I was thrilled.

I was honored.

I was humbled.

I was totally under her spell because I felt recognized.

I didn’t feel boring. I felt enough.

And all these years later, I still cherish that memory.

Here’s the thing – was Anais interesting because she was a bi-coastal bigamist who had also been lovers with the great Henry Miller? Sure.

And was Anais interesting because she made me feel “enough”? Absolutely!

Anais gave me the gift that all interesting people give – she gave me her attention.

The origin of “attention” is in the Latin word “attendere” – to reach toward. And that is what all interesting people do – they reach toward the other person by sharing stories and insights and knowledge and inviting them to do the same.

The truth of the truth is –

you can’t talk to anyone unless you’re willing to be interesting –

which simply means until you are willing to be interested in the other person.

Trust me – being interested in the other person will make you a “more than enough” person!

Do you struggle with not feeling “enough”?

Do you want to own the confidence that will allow you

to engage others without crippling self-consciousness?


To explore how one-on-one communication skills coaching can help you present you with enhanced confidence,

please contact me


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