How to Have Productive Conversations About Difficult Employee Behavior

Randy Williams wasn’t sure what to do. Despite previous conversations with his driver, Jane, about persistent tardiness, she continued to be late for her shift.

Randy didn’t have an issue with the occasional tardy. “Things happen,” he was known to sympathize.

But Jane has been consistently late for the past three months. Despite his repeated warnings, she continues to roll in at the very last minute, scrambling to leave for her route on time, creating a snowball effect on kids, parents, teachers, and other drivers. 

He pondered the situation: on the one hand, he couldn’t afford to lose a driver, especially when drivers are in short supply. Jane was trained on one of his trickier routes and losing her would mean scrambling to hire and train her replacement. On the other hand, Randy couldn’t afford for others to start coming in late. It would be far too disruptive. And, he wondered, would his team lose respect for him if he didn’t fix the issue with Jane?

Randy decided to hold one more conversation with Jane to try to resolve the punctuality issue. He scheduled a phone call with one of his liaisons in Human Resources, Phyllis Santos. With over 15 years with the district, Randy knew Phyllis had plenty of wisdom to share about holding difficult conversations. 

Randy outlined the issue for Phyllis, explaining how he talked to Jane numerous times with no result.

 “Obviously, I didn’t make a strong impression on her,” Randy said. “I’d rather not go down the discipline route if I can help it. I just want to get her back on track.”

“Got it,” Phyllis replied. “Tell me about your previous conversations with her.”

“I thought they went really well,” Randy said. “Jane would apologize, promise to come in on time, and then for a while she would. But then she would fall right back into being late again. I don’t know what to do to get her to take this seriously.”

“I think you may need to change how you’re approaching her and the situation,” Phyllis offered, “so we get a different outcome.”

“I don’t want to be a jerk about it,” he admitted, “but I also think a lot of the other drivers are looking at me and wondering if I’m going to do anything about Jane.”

“If she’s consistently late for her shifts, I assume you’ve maintained accurate documentation?” Phyllis asked.

Randy squirmed a bit in his chair, then replied, “Well, I jotted down a few times, but I haven’t kept formal notes. I mean, the system shows when she clocks in and clocks out.”

“If this is as an important issue as you claim it is, then I would assume you would have data to support your claim of tardiness. But only if she asks. Or challenges you.”

“I guess I should start keeping better documentation of the dates and length of time she’s tardy,” Randy said.

“Yes, I think so. If you sit down with her to discuss this important issue, it shows you’re truly serious if you can produce documentation over the past few weeks or months,” Phyllis explained. “It’s hard to challenge data that demonstrates a pattern.”

“Let me ask you a question,” she continued. “Why are you even talking to her about tardiness? Is this really the issue or is there something else going on?”

Randy stammered, unsure how to reply.

“No, it’s tardiness,” he said. “But I guess it’s also about trust and reliability.”

“In what way?” Phyllis asked.

Randy shifted, uncomfortably, in his seat, then explained how her tardiness can have a domino effect on the kids, their parents, teachers, and even other drivers.

“The big thing,” Randy admitted, “is I can’t rely on her anymore. And that’s tough for me. I want to be able to trust that my drivers will do what they say they’re going to do. But if she can’t even follow through with coming to work on time…” His voice trailed off.

“I understand,” Phyllis replied. “Think of it this way: there are many valid reasons why you have start and stop times for your drivers. Everyone associated is working within the same schedule and you need Jane to be a reliable member of that system. Maybe what’s been missing in your conversations with her is you haven’t really explained the negative impact she has. And that it’s just not about showing up late. It’s about trust and reliability.”

“Your job as her supervisor is to help her be successful in her position, right?”

“Right,” Randy replied.

“So because you want her to be successful, you’re bringing this issue to her attention. Suppose you asked her, ‘Jane, I’ve noticed ever since the start of this semester, you’ve been late almost a dozen times for your route. When you first started here you were always timely and on time. Help me understand what’s changed?’ you might learn some important information.”

“But why does it matter why she’s late?” Randy asked. He was getting a little frustrated with her questions.

“Sometimes you’ll discover information you didn’t know. You mentioned earlier that she runs one of your ‘trickier routes.’ Is that new or has she always run that route?”

“No, no it’s new since the beginning of the semester,” Randy replied.

“The value of opening up and having a conversation about an issue like this is you may actually discover things you didn’t realize. Is it possible this route isn’t a good fit for her?” Phyllis asked. “Is it possible something has changed in her personal life that’s creating a struggle to get to work on time? You just don’t know until and unless you ask.”

Randy pursed his lips together and thought about it. “Maybe I haven’t asked the right questions,” he said.

“None of this is to excuse her behavior. Regardless of what the excuse is — the route’s not a good fit, she has childcare issues — the issue remains that you still need to rely on her to show up on time and follow through on her promises.”

“I think you need to find out what’s behind this new pattern of tardiness. If it’s the route, or related to something at work, then you may need to identify a solution. But if it’s something she has control over — leaving earlier, for example — then she needs to identify a solution to her problem. Remember, if you’re speaking to an employee about an issue, it’s because their behavior is creating some sort of negative impact and it needs to be solved. Whenever you bring a problem to an employee’s attention it’s because you have good reason to discuss it.

“You may need to let her know if she’s unable to resolve her punctuality issue, you may be forced to pursue consequences. Just remember, this isn’t about a confrontation, it’s a conversation about an issue.”

Before they closed their meeting, Phyllis offered a summary of her tips for productive conversations.

1. Bring the issue to the employee’s attention. Explain what’s occurring versus what needs to happen (the expectations) instead.

2. Open a dialogue. Ask for their side of things. You may discover something you didn’t know that’s impacting your employee’s ability to successfully perform their duties. Be open to that possibility.

3. Allow the employee the opportunity to fix the issue. Make sure they propose a reasonable and viable solution. Brainstorm solutions, if necessary, but guard against the urge to solve their problem for them.

4. If necessary, explain the impact of their behavior.

5. Only discuss consequences if necessary. Most employees, when a problem is brought to their attention, want to fix it.

6. Don’t hold “Groundhog Day meetings.” If the problem isn’t addressed as promised, then move to consequences.

7. Follow up with employees after your initial conversation. Acknowledge if they’ve addressed the problem.

8. Finally, it’s always easiest to solve problems when they’re small. If you meet regularly with your employees, you can nip problems in the bud – before they become unwieldy and out of control.

One last bit of advice from Phyllis stuck with Randy.

“Keep in mind your reason for meeting with Jane. Is it to ensure her success on your team, or create a path for her exit? The mindset you bring to your conversations with employees will impact their outcome.”

Randy left his meeting with Phyllis feeling optimistic about meeting with Jane. He hoped she would agree to commit to punctuality. 

“Will you let me know how it goes?” Phyllis asked.

“You bet, I will,” Randy promised.

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 the forthcoming “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: karenmain.com, connect with her on LinkedIn (theleadershipexpert) or follow her on Twitter (@karenmain) or Instagram (karenlmain).