To build relationships, stop judging and start being more curious.


Portrait of Carrie, a finanance executive managing a career transition

Customer Journey: Carrie

Carrie is a finance executive who came to coaching during a career transition. Over the years that followed, she navigated new roles, organizational change, layoffs, difficult bosses, and periods of uncertainty.

Her journey explores self-leadership, resilience, confidence, and learning to take ownership of her own growth.

Each post in this series examines a real coaching conversation or leadership challenge from Carrie’s journey.

This is the second post in Carrie’s series.


As Carrie continued coaching, we explored why some people thought she was unapproachable.

“Finance is a really competitive industry. You have to have sharp elbows and a thick skin to survive. It can be a bit rough.”

I asked her to describe some rough moments in her career, and she recalled a few times in her former company being pushed out of a team and needing to find another post within the firm fast. She was good at her job, so she always got a good post, but a lot of her moves had been lateral. She wanted to learn how to be more approachable at work.

She was frustrated by her inability to move up. It was why she had applied out and was starting this new job.

We discussed the culture of her organization and what she was observing in her new position. Then I asked, “what do you like about your new boss?”

“I really like this boss,” she said. “He makes time for me weekly, compliments my work when I do it well, and encourages me to stretch a bit and try new things. He really listens to what I have to say.”

I asked her if she would describe her new boss as having sharp elbows or a thick skin.

Carrie thought for a moment. “No,” she said, “he is very political in a different way. He is positive and encourages everyone beneath him and is the same way with the people above him. He is smart, and he knows how to finesse things, not run right into them as I sometimes do.”

I told her that was a good point, and I told her about a classic Zen exercise. In the first round, one person comes toward a second person, and the second person just lays down like a doormat in front of the first person’s feet. That is not very satisfying for either person.

In the second round, the first person advances in and the second person engages their arms directly in front of them to block their progress. There is usually a struggle and sometimes one or the other makes progress, but both usually find this approach also unsatisfying.

In the third round, when the first person comes toward the second, the second person takes one of their hands and turns to walk alongside them. They both walk together side by side. This is much more agreeable to the first and the second person.

“It’s really a story about alignment,” I said. “My guess is that your boss finds a way to align rather than to oppose people, so he often finds a way to help everyone advance their goals a bit.”

Carrie liked that. “How do I do that at work?”

I asked Carrie to describe a recent situation where she had opposed someone. As she told me the story, she said that one of her team members had proposed a method for something, and she told him, “Actually, I think you should do it this way” and explained her method. He had clammed up after that, but he resisted her suggestion.

“I think my way was the right way,” she said. “I was just trying to help.”

“Yes,” I said, “but in this case, instead of feeling like you were trying to help him, he probably felt you were judging him.”

I explained that any time you use the word “should,” you are judging.

Saying you should do this or should do that implies that you know better and that they don’t know as much as you do. It creates inferiority, which is judging.

It can also feel controlling, I explained. It makes people feel like you want to control them and you want to tell them what to do. They can feel like you are micromanaging them.

“Oh my gosh,” Carrie said. “I say should all the time.”

I suggested that for her coaching homework, try to go two weeks without saying the word should, without judging. Instead, just start being curious. Ask why they want to do it that way and resist the impulse to judge whether it is right or wrong.

Carrie started at home, and almost immediately, she noticed a huge difference in her daughter. Her attitude improved, and she became more confident.

“I didn’t tell her when she was right or wrong, I just worked to understand what she was trying to do and how she felt. It was hard at first, but when I saw how much happier she was, and after I had practiced a few times, it got easier.”

Then she tried it at work.

In her new role, she had a team of two reporting to her. She stopped judging them. Instead, she started being curious, asking them to explain themselves and encouraging them more. If she wanted to make a suggestion, she did it lightly, saying something like, “if you want to try something different, you can try to do it this way.”

They started opening up about where they needed more help. She was happy to help when they asked.

“It’s so much better to help when they ask than to tell them they need help and explain it to them.”

The team started performing well and growing. Her boss even complimented her on her leadership skills and noticed how well they were doing and their good attitude.

Just becoming aware of how she was being judgmental helped Carrie find ways to be more curious and encouraging. Within a few months, she was pleased with her progress.

During one of our sessions around that time, Carrie celebrated. “I’m approachable!” she said with a smile.

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