From Frustrating to Effective: Changing Charged Conversations

Photo by Sora Shimazaki via Pexels

The following story is the second part in a short series on best practices to use when addressing challenging employee behavior. It is a continuation of a conversation between two fictional characters: “Randy Williams,” a school district transportation director, and “Phyllis Santos,” a human resources liaison for the district. (Read part one, How to Have Productive Conversations About Difficult Employee Behavior.)

Randy was a little surprised by how well his conversation with Jane went. He was on his way to debrief with Phyllis, his human resources liaison, who had previously given him some pointers on addressing his employee’s chronic tardiness.

It was the fourth or fifth time he met with his employee, Jane, who was consistently late for her route. Although Randy raised the issue with Jane on numerous occasions, the problem persisted. Out of frustration, Randy reached out to Phyllis who gave him some advice about how to structure his next conversation with Jane.

Randy replayed the conversation he had earlier with Jane. What made it so different from previous ones?

‘I was definitely more prepared,’ he reflected. ‘I was prepared to only discuss the issue of tardiness and not allow the conversation to morph into something different.’

Phyllis had warned him about that possibility and suggested he go into the meeting with Jane prepared to only discuss the one issue.

“If Jane raises other issues, take note of them and agree to discuss them, but only after you get through the issue at hand,” she said.

Phyllis also coached Randy on the importance of letting Jane solve Jane’s problems.

“Ask good questions but allow Jane to take responsibility. What is happening for her that she’s having trouble making it to work on time?” Phyllis asked. “What can she do differently?”

This time he vowed to talk less and listen more. Arriving at Phyllis’s office, Randy rapped on the door.

“Come in,” she answered. Randy greeted her and took his seat across from her.

“So,” she asked eagerly, “how did it go?”

“It went really well,” he said. “Surprisingly well.”

“Oh, I’m so glad,” Phyllis replied. “Did you come to any agreements?”

“It was a little rocky at first,” he admitted, “but in the end, I felt like we had an honest conversation.”

Karen Main is a professional speaker, writer, trainer, and consultant who specializes in...

Karen Main is a professional speaker, writer, trainer, and consultant who specializes in developing effective leaders and high-performing teams.

Photo courtesy Karen Main

The first thing Randy told Jane, he explained to Phyllis, was that he didn’t want to keep having the same conversation with her about tardiness. He told her it wasn’t fair to the others who are punctual. He asked her what she thought it’s like for the rest of the team when she is consistently late and scrambling to push out?

“That’s when it started to go sideways,” he said.

“Oh no. What happened?” Phyllis asked.

“Well, she said I was picking on her, discriminating against her because Marcia also comes in late, and I don’t do anything about Marcia.”

Phyllis nodded.

“And then the conversation somehow shifted to Noelle and how lax she is on post-trip inspections, and Jane said that I don’t talk to Noelle the way I talk to her and before I could answer, she started crying, telling me that I don’t understand the pressures she’s under and how toxic this workplace is and how she was going to report me to HR.”

He explained to Phyllis that at that point he started getting frustrated because Jane was making all of these claims that, from his perspective, came from out of the blue.

“But I remembered your advice to stay focused on the issue at hand,” he noted. “I told her that I do discuss issues with the others on the team, she just doesn’t know about those discussions, but right now I’m focused on her and her success — no one else’s. I asked her: ‘Help me understand what’s going on with you. You didn’t have this issue last semester.’”

“And then, I just listened,” he continued. “At first, she didn’t say much, but then she opened up a bit, and admitted she was frustrated by the new route and didn’t feel like she had enough time to adjust to it. Apparently, it was harder on her than I realized. We talked a lot and she finally asked if she could have her old route back.”

“That’s all well and fine,” Phyllis said, “but it still doesn’t address the tardiness problem.”

“I know,” Randy replied, “and I had the presence of mind to stay focused on that. I think I even said something to that effect, like, ‘How is changing routes going to help you get to work on time?’”

“She said she dreaded coming to work because the new route is stressful for her. I didn’t realize that the increased number of stops on that route was challenging for her. She shared a lot about feeling the route was dumped on her and she didn’t have a say in it.”

Randy added that he told Jane that he would look into giving her old route back, but if there were any more incidents of tardiness, he would have to begin the disciplinary process.

“That seemed to strike a chord with her,” Randy told Phyllis. “I told her she would have to be cross-trained on other routes and sometimes fill in on those routes and asked if she was amenable to that. Surprisingly, she was. She said ‘As long as I have my regular route and the others are temporary.’”

Randy shook his head.

“I don’t understand, but if it works, who am I to say?”

“That’s terrific, Randy,” Phyllis said. “But do you really think it’s going to make a difference in her behavior?”

“I’m not sure, Phyllis,” Randy replied. “I hope so because I want her to be successful. This may not be the right job for Jane, but I’ll do what I can to help her be successful. But I do know that the experience has given me some valuable new tools for talking with my drivers. I realize now that I talk a lot to my staff but don’t talk with them enough. I also learned that I make a lot of assumptions.”

“I think we all tend to do that,” Phyllis said. “I know I do.”

“I learned I need to check in with people more often and not wait until something is a huge fire to put out,” Randy added. “Maybe if I talked with her as soon as I saw a pattern of tardiness, this wouldn’t have happened.”

Phyllis agreed.

“I think supervisors and managers should revise how they think about meetings with employees. Do you only meet with staff when there’s an issue or a problem? If so, then employees will come to associate meeting with you as disciplinary. But if you meet regularly to discuss the person, share positive input with them, ask for their input, as well as solve problems, your meetings will take on a very different tone — and purpose.”

Randy liked that idea and vowed to begin to meet regularly with all his drivers and administrative staff. As he left her office, he considered her parting advice:

“Just remember, the conversations we have with our team members can leave an imprint on them. Let’s make sure it’s a positive one.”

Karen Main is passionate about ridding organizations of lousy leadership. Her educational programs and presentations offer clarity and practical advice to professionals as they cope with the pressures and demands of today’s workplace. Karen is the author of “Pitfalls and Possibilities: A Leadership Fable,” and offers online training on-demand, in-person workshops, and coaching and consultation through her company, Innovations in Training. Visit her website:, connect with her on LinkedIn (theleadershipexpert) or follow her on Twitter (@karenmain) or Instagram (karenlmain).