When She Had to Have a Difficult Conversation With an Employee

My former employer at Cinamour Entertainment told me that I was not dressing properly for the job. I felt that my clothes were clean, neat and decent to go to the office yet she kept insisting that I change my wardrobe. I felt harassed so I went to her higher up and indeed he said that my clothing was fine for the job. It was business/casual. I had a good conversation with her where we were both professional yet in disagreement, however, since her boss said I was fine that ended all problems.

Once I had to let a staff member go. Being the one to end someone's employment is hard. When you have a disgruntled worker who causes conflict and confusion, it can make the entire team hard to manage.

I feel one of the hardest leadership moments is when an employee says, "I don't like the way management is handling this situation." I've learned that instead of becoming defensive, it's important to listen and ask, "Please tell me what concerns you and how you feel the situation could be handled differently."

One of the most difficult parts of leadership is having a conversation with someone you genuinely value when expectations aren't being met. I've learned that avoiding those conversations doesn't help the employee, the team, or the organization. In one situation, I had to address ongoing performance and accountability concerns with a team member. Rather than making the conversation solely about what was going wrong, I focused on being clear about expectations, listening to their perspective, and discussing what support they needed to be successful. That experience taught me that honesty and empathy can, and should, exist together. People deserve to know where they stand, but they also deserve to feel heard and respected. Difficult conversations are most effective when they are timely, specific, and focused on solutions rather than blame. As a leader, my responsibility isn't to avoid uncomfortable moments; it's to create clarity, provide support, and give people a fair opportunity to grow.

Early in my HR career, I thought the hardest part of a difficult conversation was finding the right words to say. Am I being legally compliant? Am I allowed say it this way? How does what I'm saying land? I've since learned the hardest part is actually deciding to have the conversation at all, and having that conversation sooner rather than later. A few years ago, early in my leadership role, I worked with an employee whose performance had been slipping for several months. Deadlines were missed, and errors were adding up. Everyone around her had noticed, but no one had said anything directly. And quite frankly, that included me. I was new to leadership, still trying to figure out my own path and I liked her, she had been a solid contributor, and one of my first supporters of my new role. I kept telling myself it would turn around on its own. It didn't. When I finally sat down with her, I came prepared with specific examples, the expectations for her role, and a clear picture of what needed to change. All of the "right" words to say in a clear, structured way. What I wasn't prepared for was her first response: "Why didn't anyone tell me sooner? Why did we let it get this far?" Those questions have stayed with me. By waiting and "remaining objective", I thought I was being kind. Keeping it business and not personal. In reality, I had taken away her chance to fix the problem while it was still small and business is personal when you're working with people. We had an honest conversation that day. I still shared what I was seeing without softening it into something unrecognizable, and then I stopped talking and listened instead. There was more going on than I knew, and understanding that helped us build a plan she could actually succeed with. We set clear goals, scheduled regular check-ins, and followed through on both sides. Here's what I took away from that experience: 1. Clarity and transparency is kindness. Giving latitude instead of feedback feels gentler in the moment, but it leaves people guessing. Being specific and direct is a form of respect. 2. Fairness requires preparation and understanding. Bringing facts, not feelings, keeps the conversation focused on the work but doesn't take into account the person on the other end of the feedback. Documentation isn't about building a case for an employee file; it's about making sure the conversation is grounded and consistent, and you have a supportive clear path forward for the success of the person. 3. Listen more than you talk. The conversation isn't only about delivering a message, setting expectations and moving on. Some of the most important information came from her, not me. 4. Follow-through builds trust. A difficult conversation is the beginning of a process, not the end of one. Checking in afterward showed her I was invested in her success, not just correcting a problem. Difficult conversations never get completely comfortable, and I'm not entirely sure they should. That discomfort is a reminder that we're dealing with real people and real livelihoods. It's a reminder to lead with heart and with people in mind. But I've also learned that avoiding them costs far more than having them. The best thing we can offer the people we lead is honesty delivered with care, and the chance to grow from it.

Whenever I have a conversation with anyone, three words always come to my mind: Intention, Impact, and harm. I should not be causing harm by the end of the conversation but support.