What Is a Difficult Conversation?

For many years, I led teams in customer support, and the number of difficult conversations was endless. Externally, these conversations often involved service customers where I needed to push out a deadline or explain a surprise during certification testing that changed the look and feel of the product. As a leader, internal conversations were just as challenging, with some of the most difficult being layoff conversations with hardworking individuals.

If you are a leader encountering difficult conversations, whether internal or external to your team, I hope sharing these strategies will help.

Strategies for Leading Difficult Conversations

The Importance of “Why”

In difficult conversations, there are a couple of reasons they feel so challenging. The obvious one is that they typically result in an unfavorable outcome for the other party. A less obvious reason is that the news often comes as a surprise. Unexpected events usually mean deviating from a plan that already had buy in, which is why surprises are best left at birthday parties and out of the corporate world.

Explaining the “why” behind a situation helps reduce the surprise factor. As with any shock, the first question people think is, “What happened?” By providing the why, you help people process the situation faster, which can lead to a calmer and more productive conversation. One of the superpowers of the “why” is that it helps others understand the outcome is not as personal as it may initially feel. For example, during a company-wide layoff due to economic challenges, it can be helpful for individuals to hear that macro factors are at play that are outside of their control.

Understanding the “why” also helps people relate the situation to something familiar. If an engineering company has to delay a product launch because its primary engineering department is based in a country that has recently entered a war, customers are more likely to process this information better. Most people can understand that war has serious consequences, compared to simply being told their product is delayed.

Support Options and the “Pickle”

If you want to maintain a relationship during a difficult conversation, it is important to show the diligence you have taken to support the other party. The extra “above and beyond” options you prepare are what I call “the pickle.” I am a firm believer that there are many pickles of support, and the number of options really depends on how creatively you are willing to think outside the box.

The best support options come from truly understanding what the other party wants. The best way to find this out is simple: have a conversation with them and confirm their true values. Building an open relationship during a difficult conversation goes a long way and shows that you are trying to make a hard situation just a little better.

For example, if you work in customer support and need to slide a deadline, you might deliver a partial version of the product or service, share an alternative plan that meets a short term deadline, or offer some form of refund through payment, product, or services. The options can feel endless, but narrowing them down requires knowing what the other party actually values.

A quick note of caution: one common risk is offering support options based on assumptions. It is easy to think, “If I were them, I would want…” Without hearing directly from the other party, those thoughts are just assumptions, and they can be costly.

When you are truly in a pickle (see what I did there?), your support options may be limited. If you have to lay someone off and have already done your due diligence trying to find another role for them within the company, the outcome may still be that they have to leave. While the individual will understandably be disappointed, you can still do some damage control. Depending on how much time and energy you can devote, consider support beyond the company walls. Is the company offering career resources as part of the layoff package? Would you be open to connecting them with your network on LinkedIn?

Execution: Framework and Mindset

In most difficult client facing conversations, execution is the most important factor. It can be broken down into two parts: framework and mindset. You can have a strong “why” and thoughtful support options, but without the right execution, you may still be staring at an angry person across the table.

Framework

In one of my first layoff conversations, I started by explaining the “why.” The industry was in a downturn, and the organization no longer had a need for the role. I wanted to provide the macro picture, but the employee was focused on themselves. They already knew layoffs were happening and wanted to know what would happen to their job.

About five minutes into the conversation, they started breaking down. After several more minutes, which felt like decades, of frustration and anger, I finally found an opening to share that I had already begun speaking with other leaders about relocating her role. Her response was immediate: “You should have started with that!”

In hindsight, I learned that the conversation would have gone very differently if I had started with the agenda. While starting with good news can help, especially when morale is already low, we cannot guarantee how someone will react based solely on the order of topics. A safer approach is to set expectations upfront. Had I said, “In this conversation, I want to share the current state of our business, what it means for your role, and the options we are exploring to keep you at the company,” I believe I could have saved her some tears.

Mindset

Difficult conversations bring out a wide range of emotions, many of which are unstable and irrational. These situations are best handled with empathy and a calm demeanor. The worst thing you can do is try to fight fire with fire. If you have favorable options to share, it is okay to bring a bit of positivity into the conversation. You do not want to be so positive that the other person feels the difficult news is being dismissed, but being a steady and warm presence can help someone who feels lost in the dark.

Final Thoughts

As with all uncomfortable conversations, preparation is key. Be ready to explain the “why,” think through your support options, and consider how you will execute the conversation. These elements work together and can significantly change how the message is received.

Depending on how high the stakes are, role playing the scenario with a colleague can be helpful. Not only can this surface blind spots and improve your delivery, but it can also increase your confidence going into the room.

Difficult conversations will never be easy, but how you prepare for them often determines how much trust is preserved on the other side.