Turning Hard Conversations into Breakthroughs

In leadership, difficult conversations with employees are never easy. In reality, for many of us, they may be our least favorite part of the job. Hard conversations can be one of the more intimidating aspects of leading, but they are often the most essential.

There may be times when an employee suddenly appears to be slacking, but you’re not certain why. There could be someone on your team who is constantly talking over others or shutting down other people’s ideas. Maybe your team is dealing with a frustrating interpersonal conflict that is impacting the workflow. Whatever the situation may be, addressing these issues head-on is crucial. While they may be difficult because we view them as hard conversations, we can’t forget they are hard because they’re honest discussions. By exploring the truth, if your employee is willing, more often than not it will lead to a breakthrough.

This kind of action isn’t leading with force, as some may think. It is leading with compassion. In an interview with Oprah Winfrey, LinkedIn’s Jeff Weiner addressed the misconceptions of leading with compassion. “People assume that leading with compassion means not making hard decisions, not making hard choices, not transitioning people out of roles and it’s the exact opposite. The least compassionate thing you can do when someone is not equipped to be doing what they’re doing is to leave them in that role.”

While transitioning may be a necessary step at times, Weiner doesn’t just leave it there. “If that person is in the role, there is probably a reason you put them in that role.” It certainly can feel easier to avoid conflict. If we don’t take the time to have these conversations, how are we leading our teams?

To be an effective leader and see real intervention, you must be prepared to have the hard conversations. Here are five ways to approach difficult discussions that may lead to a breakthrough:

  1. Have conversations sooner rather than later. Don’t let the situation get too big. It is unfair to not address a concern earlier on and expect someone to change. As a leader, it is your place to address a concern before it escalates.
  2. Take time to empathize. Don’t simply spew out premeditated lines. Ask questions. Take a moment to understand the situation. Some employees may be facing a tragic season, and you will never know it unless you take the time to understand where they are coming from.
  3. Ask a question rather than command an action. Too often we want to tell people what to do and how to fix it. Leaders have the ability to call out the best in others by simply asking questions. Rather than challenging employees, ask questions that can lead the individual and the situation to resolve.
  4. Call out the best in your team. Motivate and encourage your people to grow. Take this moment to see the best in them. Instead of calling out the worst, speak life into your people by vocalizing their greater potential.
  5. Don’t use scare tactics. Fear-based learning is certainly not the most effective and will not bring about lasting change. Remember the power of leading with compassion and that you are both on the same team.


Learning how to navigate conflict and handle difficult conversations can be uncomfortable. They are the building blocks to instill character and a deeper work ethic among our businesses. This is why we lead. The next time you see a red flag, don’t just ignore it as a stressful situation. Remember, your next difficult discussion could lead to someone’s next breakthrough.

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