Karen, a first-time manager, was valuable to the organization but considered a difficult employee—on track to get fired if she didn’t improve her people skills.

Customer Journey Series: Karen, A Difficult Employee
This article is part of a customer journey series following “Karen,” labeled as a difficult employee. She was a first time manager in a small non-profit learning how to manage a team, motivate people, and promote collaboration.
Her journey explores empathy, communication, conflict resolution, and learning how to manage people—not just tasks.
Each post explores a real coaching conversation or leadership challenge from that journey.
This is the first post in Karen’s series.
No one ever comes to me looking to build more empathy.
However, I occasionally have senior leaders come to me seeking coaching for a difficult employee. Almost always, the engagement becomes focused on some form of empathy that is lacking.
Karen was one of these so-called difficult employees. She was a first-time manager for a small non-profit in Maryland. A friend of mine on the organization’s board had asked me to spend some time with her.
“She’s a little rough around the edges,” my friend had told me. “I think she’s valuable to the organization, but I also think she’s on track to get fired if she can’t improve her people skills.”
That was the nicest thing I heard from others who discussed her with me. Others said she was rude, interrupted others in meetings including board members, and one person described her as self-involved. There were two board members lobbying to get her fired.
While I’m sure these perceptions felt true to each person who described them, I liked Karen almost as soon as I met her. She was very smart, had a master’s in biology, and an easy laugh. It would take about a year to help her apply her innate curiosity toward other people and find better ways to communicate. After the first year, we continued to stay in touch occasionally as new issues arose that she needed help finding her way through.
I figured it was best to start with her problems, so that’s where we started. When I asked what was most difficult about her job right now, the first problem she mentioned was an employee, Richard, who reported to her.
“I give him his schedule, and half the time he doesn’t do it. Why doesn’t he just do his job?”
“That’s a good question,” I asked. “Why doesn’t he?” When Karen was silent, I put it another way. “What do you know about Richard?”
Karen was thoughtful for a moment. Then she said, “nothing really. He comes and hangs around my office wanting to chat about nothing, but I have work to do. So does he, I just don’t know why he doesn’t do it.”
“Maybe he’s just looking for some human connection,” I suggested. “Most people don’t want to be just someone who grinds away all day churning out work. They want to feel connected to the people they work with. It’s important to them that someone cares about them as a person, not just their work. They don’t want to feel like a cog in the machine or replaceable, but like a real human being with real relationships. Organizations are like small communities or big families in a way. A sense of caring matters.”
Karen was a hard worker and found meaning in her work, but she understood that someone else might need more connection to be at their best.
Performance reviews were coming up, and I suggested she give him a chance to self-evaluate. “If he thinks he’s doing a really great job, that’s a different conversation than if he is aware that he’s not meeting expectations.” We worked up a quick survey for him.
We didn’t get very far with Richard. He rated himself as exceeding expectations in every category on his self-evaluation, turned it in, and two days later resigned.
“My guess is that he felt unappreciated. It’s really hard to be enthusiastic about work if you feel like no one cares about you or what you do and just tells you what to do all the time.”
Karen started to see that managing someone was more than just managing their work and their tasks. It was about managing the person.
She was a biologist so I gave her an analogy. “You know that some plants like sun and others grow in the shade. Some grow in wet soil and some grow in sandy soil. Every plant has different needs.”
Karen nodded.
“It’s the same with people. Everyone has their own needs. Some like to talk more, some prefer the quiet. Some like paperwork, and some like field work. I wonder if you can apply the same curiosity you have with plants to people and start paying attention more to what they need to thrive.”
Karen understood that and started to make a point of making better relationships at work. She was sorry that she had not been a better boss for Richard, and dedicated herself to being better in the future.
Prioritizing People
It was for a similar incident in the past that Karen had gotten in trouble with a board member in the first place. A few months earlier, Karen had been in charge of restoring plants in a section of the conservation holding. It was right next to private property.
As she was installing some native plants, a neighbor came out of the house yelling at her and accusing her of being on her property.
Karen became defensive and told the woman it was her job to plant the bushes.
Unfortunately, the woman was a close friend of two other people on the board and she called them and gave them an earful about how rude Karen was. The two people on the board wanted her gone right away.
The Executive Director liked Karen and felt caught between two forces—powerful board members and a valuable employee. This is why I had been called in by a separate board member.
When I talked to Karen about it, she was a bit contrite. “As I look back on it, the line between our property and hers was not well defined. But she came out yelling, and it was my first impulse to defend myself and yell back. I know it was not my finest moment.”
I suggested that Karen complete an emotional intelligence assessment, which I offer to all my clients. “It might give us a better hint on where to go from here,” I said.
So, at the end of our first few sessions, Karen had started to turn her curiosity more toward people. She was more curious about herself and her emotional intelligence, too. As she started to turn her attention outward, the behavior that was making her a difficult employee started to decrease.
Continue the Journey
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