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Talking Tough - Handling Difficult Conversations

Most people don’t enjoy confrontation. Telling someone that they are underperforming, handling conflict between two employees, or dealing with toxicity is a challenge and a necessary evil as part of leadership. As difficult as the situation may be, taking care of it head on not only addresses the immediate issue, but also shows the rest of the team that you are willing to tackle the tough stuff.


Whatever the circumstance, you can take certain steps to handle the conversation smoothly and to preserve the integrity of the people involved.


  • Prepare. In his book Exactly What to Say, Phil M. Jones writes that “the worst time to think about what you’re saying is when you’re saying it.” You know that the serious talk is coming, so take some time to prepare, or even practice, what you’re going to say. Know your speaking points ahead of time, and evaluate them to remove any emotion or personal bias. Even with a plan, allow yourself to be flexible in your statements and responses, depending on how the conversation goes.

  • Do it now. Address the issue sooner than later. Better to handle a problem while it is small and manageable, rather than waiting for it to affect the dynamic of your team or your department. Nothing will kill the morale of a team faster than a leader who tolerates negative behavior, performance, or attitude.

  • Be concise and transparent. Stick to the facts. Don’t use ten words when five will do. Be honest, clear, and non-emotional. Use “I” statements and focus on the other person’s behavior and the impact of that behavior, not on the person themselves. “I noticed that you didn’t submit the required documents and missed the deadline for our project. As result, we are at risk for losing this client,” rather than, “You missed the deadline because you’ve been lazy about completing your work.”

  • Listen. Allow the other person to speak, be open to their replies, and don’t interrupt. Be empathetic: if the words are difficult for you to say, they’re going to be more difficult for the recipient to hear. Ask clarifying questions to be sure you understand your employee’s concerns.  At the same time, keep the conversation to the necessary points, and don’t allow for tangents and non-related issues.

  • Follow up. Before going into the conversation, know what the desired outcome is. If you are going to retain the employee, set clear expectations and actionable next steps. Agree to a time frame, and send a meeting invite for the next discussion.


If you go into the situation prepared, if you’re authentic and kind in your delivery, and if you seek a positive resolution, your tough conversation might feel slightly easier for everyone involved in the dialogue.

two businessmen with boxing glove


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