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?

Do People (especially “men people”) Interrupt You?

To be nobody but yourself in a world which is doing its best, night and day, to make you everybody else – means to fight the hardest battle which any human being can fight; and never stop fighting.



Last month Mari, a department head at an international concern, brought me in to do some strategizing with her team which happens to be made up of all women. Mari reports directly to Mark and he routinely offers more resistance than support. While there was some griping throughout the half-day session, Mari and her team reckoned with what they could not change and then strategized for practical workarounds and next steps.

Afterwards I met with Mark. He had asked to speak with me and I presumed he wanted to discuss Mari and the department. I was wrong! In passing he said she’s a solid performer but that she has unrealistic expectations of people. He then proceeded to talk to me about the five admin. assistants who report to him. He’s at his wit’s end as they take up his time complaining about each other. He said he didn’t know what to do. Pause. “You know how women can be,” he smirked.

I was gobsmacked! His throw-away line was stunning on so many levels. I’m not naïve BUT I seldom encounter a man who is so blatantly dismissive and clueless.

Cut to this week.

Tuesday we had the double-header of an Uber Board member talking smack about women talking too much, coupled with Senator Kamala Harris, Democrat of California, being chastised/interrupted by male colleagues as she questioned Attorney General Sessions during his testimony before the Senate Intelligence Committee.

An article in the New York Times observed that, “Both incidents triggered an outpouring of recognition for what is commonly accepted as fact – that being interrupted, talked over, shut down or penalized for speaking out is nearly a universal experience for women when they are outnumbered by men.”

As of Thursday night that Times article has received over 1300 comments!

My friend Deborah, a senior VP at an international financial institution circulated the article among close associates. Here’s just one comment from the email thread:

“When my job was eliminated 12 years ago, two other female first Vice Presidents also were let go, thereby eliminating ALL of my boss’s female direct reports. No men at our level were released, only a few low level men to ‘balance’ the list. And yes, my boss would shoot down my ideas and then present them as his own. It was the price women were supposed to pay for being ‘allowed’ to work in a Man’s World. It’s beyond disturbing that in the 40+ years since many of us entered the workforce this hasn’t changed.

Why is this beyond disturbing? Why would things change? Nothing and no one changes on its own (and if you’re receiving this newsletter, you know me well enough to know I’m not being flippant).

Obviously, this is a multi-layered, vexingly complex challenge. Within the space of this newsletter, though, I want to remind you –

We all do what we do and say what we say AND do it in the way we do it and say it in the way we say it for a reason. No one just is! Men were not born with a gene that compels them to interrupt. Women were not born with special eardrums that allow them to listen more attentively.

We learn how to communicate. We’re socialized to use language. And, yes, stereotypically little girls and little boys are socialized to use language for different purposes. But (there’s always that “BUT”) – take my client, Richard. . .

In our first meeting he told me that he hates when people interrupt him. He thinks they’re rude and disrespectful. He said his team constantly interrupts him.

The following week I sat in on a meeting with Richard and six of his team. Early in the session, one of the team members interrupted Richard and he immediately shut down. Everything about him changed – his face, his posture and his overall “vibe.” However, I thought the team was “lively” and not necessarily rude.

Richard later told me that when growing up his parents insisted that he and his siblings not interrupt when adults spoke – they didn’t allow for freewheeling discussion. The family motto was: “polite people don’t interrupt and we are polite people” (though his father wasn’t quite so polite when he had had affair when Richard was thirteen).

Although Richard wasn’t ready to give up labeling his team “rude” we were able to strategize ways for him not to shut down and not yield the discussion to the person with the loudest voice. He learned to restrain his judgment as well as how to lead a more productive, yet still lively, meeting.

We are each responsible for our voice. Give up your power and you do become a victim.

Easy for me to say – I’m a man and not a woman. However, I’ve coached enough women to know that there are strategies for managing boorish men so as to assert oneself!

This month I feel heartened by a team of dynamic women who continue to find ways to lead despite an incompetent VP.

This month I feel challenged by a group of women who are happy undermining each other much to the amusement of an emotionally dense boss.

And this month I’m relieved that Kamala Harris is not prepared to roll over.

Somehow all of this challenges me – and I hope you – to strive to be more honest with our own self, more demanding and more committed to finding our voice and using that voice from a place of confidence.

To do less would be “beyond disturbing.”