How to Have the Difficult Conversation

To be a successful leader, we need to be intimate not only with our strengths, but also with our inclinations to avoid conflict — which often means avoiding the difficult conversation.  Sometimes we may prefer to offer excuses for postponing the conversation or downplay its importance.   Perhaps we are searching to find the right words at that moment; or we really want to avoid any emotional reactions.

What really stops us from engaging in the difficult conversation?

I believe what makes difficult conversations more difficult is our lack of confidence in how to turn these interactions into constructive and beneficial discussions.  Because, the purpose of any discussion is not to just make a few key points and emotionally walk away, but rather to connect and come to an understanding with the other person.

Tips to help you, as a leader, have hard conversations without feeling like you must avoid them anymore.

  1. Plan but don’t script the conversation.
    It can help to plan what you want to say by writing down a few key points before your conversation. You want to acknowledge the other person’s perspective and keep your language clear, simple, direct and neutral.
  2. Acknowledge and appreciate their accomplishments.
    With sincerity, let the other person know that you are aware of the things they do well.
  3. Ask questions to gain understanding and insight.
    A difficult conversation tends to go best when you think of it as a normal conversation.  Be curious and inquiry “how can we work through this issue?”  Asking open-ended questions can often lead to a possible solution.
  4. Self-manage your emotions and keep the conversation going.
    Experience tells us that these conversations often lead to “strained” relationships, which is painful. You may need to slow down the conversation, listen and avoid any feelings of anger or resentment, which is non-productive.  Be considerate, be compassionate.
  5. Reflect and learn.
    After a difficult conversation, it’s worthwhile to consider what went well and what didn’t.  Think about why you had certain reactions, and how you might respond differently in the future.

Handling a difficult conversation effectively is more than a skill, it’s a demonstration of strength and confidence.


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