What I Learned From My Most Challenging Coaching Client – Ever!

Earlier this year Holly (name changed) took a workshop from me on “dealing with difficult people.” At the end of the day she confided that the big take-away was that she is a difficult person – not her clients. With candor she confessed that she doesn’t like talking to people because she’s just not interested. What made Holly’s revelation surprising is that she’s a psychotherapist in private practice.

She explained that she’s fine for the fifty-minutes insurance pays for, but it’s the few minutes prior and after the session that she dislikes. She asked if I could teach her to “like” people. Given that she’s a therapist, this was one of the odder requests asked of me. And it raises the question – can you learn to like people?

In some respects, Holly reminded me of several of my relatives!

By the time I was born both my grandfathers were dead. My paternal grandmother was a prison guard for thirty-five years. My maternal grandmother was such a miserable creature that not even her own cat would sit on her lap! Neither grandmother had any friends.

My parents were fun, funny people who had no friends because people were not to be trusted. My brother and I weren’t even allowed to go trick-or-treating as my parents viewed it as a form of begging.

Although my grandmothers and parents didn’t have any friends, they all loved to sit on park benches or by a window and just watch people. They enjoyed imagining what kind of lives people lived (most were deemed unhappy).

As a child I observed people from a distance and from that distance I longed for the chance to “like” people. Because I spent most of my childhood on a park bench, I could have grown up to become a hermit. Instead, I traveled the world, embraced adventure, entered ministry and became a teacher, coach and speaker.

I’m fascinated with people, yet in my communication coaching I’ve encountered scores of individuals like Holly. They share the common refrain of, “I’m not interested in listening to people’s stories; I just want the facts.” These people want me to help them learn how to enjoy people because their frustration is telling them that something has to change.

I wasn’t able to give Holly a tip-sheet on “6 Easy Steps To Liking People.” While I could tell her why she should like people (success in life = the people you meet + what you create togetherthank you Keith Ferrazzi), I couldn’t tell her how to like them.

In our coaching sessions I worked to help Holly develop a curiosity for people since curiosity is at the heart of liking. I gave her a list of questions that I hoped would serve as a “whack on the head” to help her clarify her feelings of dislike (see end of post for that list).

As a therapist, Holly was intrigued with my questions but as “Holly” she was resistant to them. Through our coaching sessions, she realized that she didn’t like people because she thought they wouldn’t like her – the non-professional “Holly.”

In one telling throwaway line, Holly mentioned that her mother used to tell her that she was “an uninteresting girl.” Holly’s fear was that outside a professional setting, people wouldn’t find her interesting and because of that belief Holly pushed people away before they could push her away.

As our sessions progressed, it also became clear to both of us that she had a superiority complex and that’s why she erupted into condescending fits with people. Fear made her a harsh judge and judging gave her safety. However, it was a “safe” place that prevented her from being truly interested in people. If you believe you’re better than most everyone else why would you be interested in them?

My time with Holly ended abruptly. She lost interest and admitted she was content not liking people. As with many people, fear won out. Although she was paid to hear people’s stories she was afraid to hear her story in theirs and so recognize her own genuine worth.

So here’s the thing – maybe you can’t teach someone how to like people. And maybe it’s not even necessary to like people (though how lonely a life). You can, though, learn how to feel compassion.

I don’t like everyone I meet. I do, though, enjoy being surprised by people. By their stories. By how their stories often contradict who I thought they were based on looks, dress, mannerisms and occupations.

While growing up I was convinced that I was a boring person and I was worried that people would uncover my secret. To deflect attention away from “boring me”, I learned to interview people and marveled at how readily most people would talk about themselves.

I love a good story. And all the good stories I’ve been regaled with in my life have enhanced my compassion.

The enduring truth is that if you want to learn how to like people, you have to stand with your shoes off in the presence of the whack-a-do mystery of other people.

You have to risk finding shards of your story in their story.

You have to become curious.

And when you become curious then you will find the boy on a park bench sitting alongside a not uninteresting girl.

It’s only there you can ever really hope to “like” people.


Top Ten Questions To Generate Curiosity For People

  1. Why don’t you like people? And since your first answer is just the superficial reason, what is the real reason? Which is another way of asking, what are you afraid of?
  2. What is the best conversation you ever had with a stranger?
  3. What makes a person boring for you?
  4. What makes you boring to people?
  5. Do you want people to like you?
  6. Do you have anything to give to people that would benefit them?
  7. In what ways is your life richer for “excluding” people? (yes, trick question)
  8. Who was the kindest person to you?
  9. Who was the nastiest?
  10. Who knew you the best – the kindest or the nastiest?