SOS: My Client Couldn’t Stand His Boss

11/9/26

STORY

He said that his manager wasn’t supportive.

She micromanaged, gave little feedback, and didn’t seem to care about him as a person.

He would share ideas, and she would ignore them.

He said…

“I feel unseen, unheard, and underutilized.”

I asked him to tell me more about his manager.

What’s her personality like?

Is she married?

Kids?

What does she like to do for fun?

He didn’t have any clear answers to these questions.

He said she was very closed off.

Anytime he tried to ask about her life outside of work, she would change the subject.

I empathized with his situation.

I can sense he was frustrated and at a loss as to what to do next.

I asked him…

“Could I offer you a challenge?”

He was open to it.

I said…

“Next time you’re alone with your manager, ask her how she’s doing. But don’t just ask that generic, surface-level ‘how are you’ where the person on the other side knows that you don’t really mean it. Ask it sincerely. Look into her eyes, slow your pace of speech, and ask her with genuine curiosity…‘how are you?’“

He was resistant at first, but the more I explained why he should attempt this, he accepted the challenge.

Two weeks later, we had another call, and he told me what happened.

He said…

“Jay, I did what you said, and I couldn’t believe what happened. She opened up to me. She told me about the pressure she’s under. She explained how she feels so alone in her role because the VP never checks in on her. She said she felt like she couldn’t talk to anyone, and the stress of her role was really getting to her. She wants to make things better for the team, but no one listens to her. This went on for over 10 minutes, and I just listened. I felt bad for her. I realized that she’s doing her very best, and even though I disagree with a lot of how she behaves, I understand her better now.”

I replied, saying…

“So she basically said…

‘I feel unseen, unheard, and underutilized.’“

I could see it in his eyes; it clicked.

The two of them were feeling exactly the same way.

It was a vicious cycle of her manager treating her one way…

Which then led to her treating him the same way…

And everyone feeling unseen, unheard, and underutilized.

We then discussed how to break this cycle.

I told him you break the cycle by leading with compassion.

That does not mean resigning to poor behavior and allowing people to treat you badly.

Leading with compassion means responding with a clear understanding of what the other person is experiencing.

And from then on…

His relationship with his manager changed.

She didn’t all of a sudden become a perfect leader…

But he was more capable of coaching up and not being so triggered by her actions.

Look…

Everyone is going through something.

And while you shouldn’t have to resign yourself to micromanagement and poor leadership…

You also get zero value out of resenting your manager and seeing them as the “villain” in your story.

Instead, seek to understand them.

Be curious.

Get to know why they are behaving as they are.

It may be the difference between just surviving at work…

And thriving at work.

OBSERVATION

(This observation was written with the help of AI)

Psychologists Linda Shanock and Robert Eisenberger studied how support flows through an organization. They found that managers who felt supported by their own organization were seen by their employees as more supportive, and those employees, in turn, performed better. In other words, support trickles down, and so does the lack of it. A manager who feels unseen and unheard often passes that same experience to their team, usually without realizing it. That’s why curiosity and compassion can break the cycle: sometimes the person who seems like the villain is just the next person down the line.

(Shanock & Eisenberger, When Supervisors Feel Supported: Relationships With Subordinates’ Perceived Supervisor Support, Perceived Organizational Support, and Performance, Journal of Applied Psychology, 2006)

STRATEGY

This week, I invite you to get curious.

Next time you’re in a meeting with someone whom you perceive as difficult…

Get curious.

Ask yourself…

What is this person really going through?

What’s it like to be them?

What are they experiencing?

How are they feeling about their work?

What challenges may they have that I haven’t considered yet?

To take it a step further, I offer you the same challenge I offered to my client.

Ask them how they’re doing, but do it sincerely.

It needs to be genuine.

You need to actually be interested in the answer and seek to understand them.

Warning: this simple approach may completely transform your relationship with them (in a good way!).

Rooting for you,

Jay (inviting you to lead with compassion)

Global keynote speaker

Host of the “Unstuck” podcast

Not a fan of the show “Nobody Wants This” (season 1 was okay, but it got worse and worse, and season 3 was just awful)

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