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Powerful Tools for Navigating Confrontational Conversations

Let’s talk about having the hard conversations. Confrontation. Conflict.

Having the hard conversations is one of the greatest favors you can offer your teams (and yourself).

It’s a favor because if you are feeling something is off, you can bet that they feel it too. Ignoring things only prolongs negative feelings and enhances the difficulty of a problem. Experiences, contexts, and situations are better when we address the elephant in the boardroom and have the hard conversations.

Having the hard conversations might be uncomfortable for you or the other person. Maybe for just one of you or both of you. These conversations may be familiar to one of you, both of you, neither of you. It depends on life and workplace experiences from your pasts.

Either way, here are some tools to put in your kit for hard conversations. These will help you confront the conversations that need to be had when something is not quite right.

  1. Be Curious: If you are familiar with my work at all, this should come at no surprise. I recommend your first step be to pause and ask questions. Be intrigued by the situation and the person, and avoid assumption. This is where you respond instead of react. And use an intentional approach to the conversation so as to avoid anyone feeling shame or reprimanded.
  2. Know your Intentions: Be clear on why you are wanting to address the situation. Are you trying to solve a problem, or looking for an apology? Is this important to progress and productivity, or does it feel personal? The more clear you are on why this is important, the more constructive the conversation will be (your approach will look different).
  3. Confirm or Correct: This is a follow-up to being curious. After someone has spoken and it’s your turn for a reply, begin by asking some questions to ensure you really understand, and so that they feel heard. This is an opportunity for them to either confirm that you get it, or correct and clarify.
  4. Serve it on a “Platter”: This is about setting expectations and asking permission. It goes something like this – “I’ve noticed that there have been some miscommunications between you and I recently, and I’d really like for us to figure out a solution. Is now a good time?” You are letting them know what you would like, it’s ‘us against the problem,’ and you are asking permission. Asking permission helps to get buy-in, and ensures that they are in a good headspace to make the conversation productive.
  5. The 3 C’s: This is an adaptation of a tool from another brilliant mind in this industry. The 3 C’s in order are: Curious, Confused, Concerned. These are meant to be used separately and progressively as a situation escalates. It would go something like this: “I’m curious. Our weekly meeting is always on Tuesdays at 8am but arriving at that time consistently, seems to be an issue.” And then you pause and let them fill in some information. Then you talk it out and come to an accountability agreement. You bring the subject up again with ‘Confused’ if it continues to happen. If the first one or two conversations are done well, hopefully you don’t need to get to ‘Concerned.’ (This is a good place to think about your tone of voice. Make statements and avoid a tone that shames or belittles).


In addition to helpful recommendations, here are a few things to avoid.

  1. The Compliment Sandwich: Don’t do it. It isn’t novel, it doesn’t feel genuine, and people expect a “but” which completely negates the compliments. You can be respectful without trying to cushion a conversation with compliments. And, to be honest, this is usually a tool used by someone who is uncomfortable themselves – so it really makes the conversation about them and not the person they are approaching.
  2. Role playing the conversation in your mind: This may seem like a good preparatory tool, especially if confrontation makes you uncomfortable. But this will really only cause anxiety and worry. Besides, you don’t have a crystal ball that can predict how someone will react or what they will say. The best thing you can do is be clear about your concerns and what you want to be sure is communicated. Then be present in the conversation and listen to understand. If you really want to practice something, just practice saying specific words out loud. For example, if telling someone “no” is hard for you, say it out loud to yourself so you can get used to the sound of it coming from your voice. (BONUS: read here for two types of communication related to this point).
  3. Avoid “you” talk: Maybe you have heard this before, but it’s because it’s a good point. Using “you” statements can make someone immediately defensive. It’s a natural reaction to try and protect one’s self. You can speak about yourself using “I” statements, but instead of “you” speak to the situation rather than the behavior of the person. [GOOD]> “It’s difficult for me to do my work well when things come in at the last second.” [BAD]> “I can’t do what I need to do when you’re always pushing the deadline.”


There are some more advanced tools such as reflective statements or being able to point out a behavior to someone who may not realize they are doing it. If you are interested in knowing more and talking through an issue you are having send me a DM – I am more than happy to help 🙂


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