Key Takeaways

  • How leaders approach difficult conversations can influence how employees respond, learn from mistakes and move forward.
  • Effective leadership communication balances accountability with empathy, clarity and a focus on improvement.
  • L&D can help managers build difficult-conversation skills through realistic scenarios, role-playing, coaching and opportunities to practice before challenging situations arise.

Recently, my daughter had to tell me about a grade she knew I wasn’t going to be very happy about. But before she told me, she did something that made me smile afterward.

She asked how my day was. She gave me a hug. She told me she loved me. We talked for a little while and then, eventually, she told me about the grade. Of course, by that point, I knew something was coming.

The grade didn’t change. My expectations didn’t change. We still had to talk about what happened and what she could do differently next time. But the way she approached me changed the conversation completely.

Later, I kept thinking about it. My daughter had instinctively understood something that we sometimes forget in the workplace: It is not only what we say that matters. It is also how the message lands.

The Message Is Only Part of the Conversation

Working for more than 20 years in clinical research and with teams, I have been on many sides of difficult conversations. I have had to give feedback, receive it, address problems and have conversations I would much rather not have had. One thing I have learned is that people remember how those conversations made them feel.

Early in my career, a concern came to me about someone I worked with. I remember thinking that I could easily take it to her manager. But before doing that, I wanted to talk to her myself. I wanted to understand what was happening, so we sat down and talked.

I asked her what was going on. We discussed what needed to improve, but I also asked what I could do to help and what might help her become stronger in that area. The issue was resolved.

It wasn’t some major leadership moment. At the time, I probably didn’t even think of it as leadership. It simply felt like the right thing to do before involving someone else. I still think about that conversation because, throughout my career, I have seen how differently things can go depending on how we approach them.

There are absolutely situations that need to be escalated. In clinical research especially, there are issues involving patient safety, quality, compliance and performance that cannot simply be handled informally. Leaders have a responsibility to act when something requires action. But not every difficult moment has to begin with escalation. Sometimes, a simple conversation is enough. And sometimes, even if one conversation doesn’t solve the problem, another conversation is worth having.

When the Message Gets Bigger Than the Problem

When too many people are brought into an issue too quickly, something else can happen. What may have started as a relatively manageable concern can suddenly feel enormous to the person on the receiving end. They become nervous. They may shut down. They may stop asking questions because they are afraid of saying the wrong thing or making another mistake. Instead of thinking about how to improve, they start worrying about what is going to happen to them.

That is where I think leaders need to stop for a moment and ask themselves a very simple question: What do I want this person to do after this conversation?

If I want someone to improve, then the way I communicate should leave room for improvement. That doesn’t mean avoiding accountability. It doesn’t mean making every difficult message sound positive. And it certainly doesn’t mean ignoring problems. People deserve clarity.

Before the Conversation

I don’t believe there is one perfect formula for delivering feedback. People are different, situations are different and some conversations are much harder than others. But there are a few questions I have learned to ask myself:

  • Have I spoken directly to the person before making assumptions?
  • Do I understand what actually happened?
  • Does this need to be escalated now, or would a one-on-one conversation be appropriate first?
  • And probably most importantly: Will this person leave the conversation with an understanding of what needs to change?

That last question matters. Saying, “This isn’t good enough,” identifies a problem. Talking through what wasn’t working, what needs to look different and what support may be needed gives someone somewhere to go next.

There is also something very powerful about asking, “What happened?”

It sounds simple, but asking that question before reaching a conclusion can completely change a conversation. Sometimes there is information we don’t have. Sometimes expectations weren’t as clear as we thought they were. Sometimes the person made a mistake and knows exactly what went wrong. But we don’t know until we have the conversation.

Where Learning and Development Comes In

This is where learning and development (L&D) has an opportunity to make a real difference. We teach leaders a great deal about processes, policies and performance management. Those things matter. But difficult conversations are human interactions, and they are hard to learn from a slide deck.

People need opportunities to practice them. Give managers realistic situations and let them work through them. What do you say when an employee becomes defensive? How do you address a mistake without making someone afraid to speak up the next time something goes wrong? When should a manager continue working through an issue directly, and when is escalation necessary?

Role-playing, coaching and real-world scenarios can help leaders become more comfortable with these moments before they are sitting across from an actual employee. It can also help leaders understand that empathy and accountability are not opposites.

You can have high expectations and still be thoughtful about how you communicate with them. You can address a mistake and still make it clear that you want the person to succeed. You can have a difficult conversation without making someone feel small.

Those distinctions matter because the conversation doesn’t really end when the meeting ends. The person walks away with it. They may replay what was said. They may change how comfortable they feel asking questions. They may become more confident, or less confident. And they may decide whether the next time something goes wrong, they will come to you early or wait until they absolutely have to.

What People Carry With Them

That is why I keep coming back to that conversation with my daughter. She wasn’t thinking about leadership or communication theory. She was simply thinking about the person on the other side of what she needed to say. There was still a grade we needed to discuss. There was still accountability. There were still expectations. But there was also a relationship she cared about.

We cannot always change the message we need to deliver but we can think about how we deliver it. We can ask one more question before making an assumption. We can have one more conversation when it makes sense. We can be clear without being unnecessarily intimidating. And we can remember that there is a human being sitting on the other side of our words.

Because sometimes what changes what happens next isn’t the message itself. It’s the landing.