Eventually, all leaders find themselves in difficult conversations. It might come as a result of a conflict between team members, as part of a sensitive coaching/feedback discussion, or when reconciling different ideas for how to proceed on a project. There may be weeks or months between them, or you might have three difficult conversations in one day. How they show up and how frequently they do so can vary from team to team. The one constant for all teams and all leaders is that they will show up.

The challenge with difficult conversations is usually the emotional context. People either misunderstand, or feel misunderstood, and emotions rise. As emotions rise, clarity of communication falls, there are more misunderstandings, and – well, you get the idea. It’s messy, it’s complicated, and they can spiral out of control

One way you can reduce the negative impact of rising emotions is to create more clarity and understanding between people. Three question/phrase types I have found to help with clarity and understanding are:

  • Tell me more 

With the “tell me more” question type, you are inviting the other person to give you more context and more detail. You are seeking more than just a surface understanding of the situation. 

You can use “tell me more” either as a question or as a statement.

  • “Can you tell me more about _____?”
  • “Please, tell me more.”


  • Help me understand 

The “help me understand” question type is a variation of the “tell me more” type. It gives you a different way to get more information about the context or detail of a situation or problem without repeatedly saying: “tell me more.”

It often sounds something like:

  • Please help me understand how ____ happened?
  • Can you help me understand how that information came to you?
  • I’m trying to get a better grasp of what was going on when ___ happened. Can you help me understand what else was going on at that time?
  • Can you help me understand how you see this issue/problem?
  • Is that right/correct?


An “is that right?” question is an effective way to wrap up and check with the other person after you have summarized your understanding of a situation.

Here’s how this question works:

  • If I understand correctly, you got this information from ____. Is that right?
  • I think I understand what happened, now. You saw ____ happen, and you did ___ as a result. Is that correct?
  • Oh. I see. So, ____ happened, and that looked like ___ to you, and then you did ____. Is that right?
  • Here’s how I understand our plan. I’m going to get ___ for you by ___, and you are going to do ____ by ___. Is that correct? 


As with all communication techniques, there is more to it than just the words. You also have to consider tone and body language. Even a well phrased question can communicate a negative message if the tone or body language is off. Controlling your mindset is the most effective way I’ve found to control my tone and body language.

When I find myself trying to prove I’m right or “win the argument,” both my tone and body language tend in the aggressive and accusatory direction, and the questions/statements above sound more like attacks than questions.

When I keep my focus on understanding the other person more than I focus on winning, my tone and body language communicate my desire to understand, and the questions/statements above work amazingly well.

If you will practice both the mindset of understanding the other person over winning the argument and apply the three questions/statements above, you will find yourself resolving difficult conversations more than you escalate them.


Do you have more questions about difficult conversations and better ways to communicate? Join us for Virtual LeaderCon, a four day free event with over 30 leadership experts. Join us and get your questions answered!

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