How do you start a difficult conversation at work?

You might be here because you’ve got one that you need to have. You’re in the right place. I’m Chad. My co-author and I wrote a book called Ask Powerful Questions Create Conversations That Matter. We used to work with an organization and our job still is to train and coach leaders to facilitate and lead conversations on really difficult subjects. Things like race relations long-term conflict, politics, etc. Things we don’t typically want to talk about. That also includes difficult conversations like how to let somebody go, how to give somebody really difficult feedback, etc.

Blog Note: The following is an adapted and edited transcript of one of our daily YouTube tutorials. We know sometimes it is easier to scroll through written content which is why we are publishing here. Because of that, there may be typos or phrases that seem out of context. You’ll definitely be able to get the main idea. To get the full context, visit our YouTube channel here. And if you want to watch the video on this topic specifically, you can scroll down to the bottom of this post to access it as well.

In this video, I’m going to share 3 really concrete practical strategies that you can use to have more difficult conversations in a more impactful way. And I’m also going to share a really intense example from my own life. To be able to do that, I want to share with you about a tool that really changed the way that I view difficult conversation. It is very simply the difference between content and process. There’s always as you’re having a conversation. There’s always something going on underneath that conversation. 


Content is what you are talking about. If content is at the surface layer, it’s the topic that you’re talking about. If content is here, the tool is to stop talking about the content. Drop down to what’s happening underneath that which is the process of that conversation. The process is how you are talking about it. If the content is what you are talking about, the process is how you’re talking about it. You might be talking about letting somebody go but you might be entering the conversation with a level of judgment. They might be entering the conversation with the level of fear. Those are all right things and how you’re having the conversation.  Let’s just dive into strategy number 1 on how you can start a difficult conversation.

Move Yourself and  Move the People

The first strategy is to move yourself and to do things that move the people you’re talking with from a mindset in a place of making assumptions to exploring possibilities. When we’re in this mindset of making assumptions rather than exploring possibilities, our conversations can start to get very heated. Can start to get very heated and go down a path that isn’t even grounded in reality or truth.  The strategy to move from making assumptions to exploring possibilities is literally to up your question count. Often when we have difficult conversations or we have to have difficult conversations, we think about, “What am I going to say? How am I going to frame this? Should I give them some positive feedback and then some negative feedback and then some positive feedback?” We’re thinking about what we’re going to say. I would invite you to use the strategy of “What are you going to ask?”  

How can you enter this difficult conversation with a question that moves you and them from the place of making assumptions to exploring possibilities. The easiest way to do that is to check in with yourself and ask yourself what are your assumptions and turn one of those assumptions into a question.  If you assume that somebody is going to break down in tears or get very angry when you have a conversation about letting them go, question that assumption. How can you figure out a way to transition that idea that assumption into a question. Now, some assumptions, we are pretty good at guessing and we’re like, “We know that this is going to happen.” Maybe you don’t need to question those. But  question the assumptions that you’re not quite sure whether this is the way that things are going to work out. 

Right Conversation Vs. Level of Openness

Strategy number 2 is probably really palpably felt in your world.It’s this idea of entering a conversation with a need to be right versus a level of openness. That means oftentimes when we enter a hard conversation, we try to map out how it’s going to go. It never goes that way. Just a fyi. Moving from this place of need to be right… This isn’t just like, “Oh, I need to be  right.” This is like a need to be right. In fact, I would say the amygdala the part of our brain that developed first that you know, the part that controls the fight-or-flight response. I don’t think that it’s just fight-or-flight because you know there’s no saber-tooth tigers in our world. Now, we’re not running away from that physical threat. I would argue that it’s actually a fight flight or a need to be right that’s showing up in that brain. When that part of our mind turns on, that difficult conversation is going to take a very steep downturn, right? How do you move yourself and the people that you’re in conversation with, the person that you’re in conversation with from this mindset of a need to be right to a level of openness? 

The tool here is really simple. Admit your mistakes or phrase differently. Own your own contribution to this given dynamic. Typically, when we have a difficult conversation, we kind of enter in with this blame mindset of finger pointing, right? We’re pointing at this person and this doesn’t feel very good. A really disarming way to move from a need to be right to this level of openness is simply to own your own contribution, own your contribution to that dynamic. It’s powerfully disarming and what happens to the other person is that they feel led by example to their own contribution to a particular dynamic. Strategy number 2, own your mistakes so that you can shift from a need to be right to this mindset of openness.

Listen to Understand

Strategy number 3 plays off of this idea that listening is being able to be changed by the other person. In difficult conversations, we focus so much on what’s coming out of our mouth and we fear so much what’s going to come out of somebody else’s mouth that we forget to the fact that we have these two appendages on the side of our head that allow us to take in information and use it to make our conversations better. And so the third strategy is shifting from this place of listening to win to listening to understand. This is where just for a minute, you set aside all of your opinions, perspectives, experiences and you’re just really present listening to that other person.  Listening to understand. I would even argue that the level 3 version of that is listening in a way that you’re willing to be changed by the other person.It doesn’t mean that you need to change the outcome or your opinion on something. But listen in a way that you’re willing to accept that they might know something that you don’t. It’s a really powerful shift in the conversation that is very honoring to the other. Again, very disarming as well.

The tool to be able to shift from a place of listening to win to listening to understand is very simply follow your curiosity. Typically in a difficult conversation, we don’t have curiosity. We think we know what we’re going to say, we kind of map out how we want it to go, we expect and make assumptions about people’s response. To move from a place of listening to win to listening to understand. Very simply, I would invite you to listen as the person’s talking and figure out what are you naturally genuinely curious about and ask a question rooted in that curiosity. That will shift your brain and their brain from a place of listening to win to this place of listening to understand where actual change can happen. You can talk about really fiery topics all in a very simple peaceful calm way. When I was working for this organization world in conversation, getting groups of people together to talk about race, relations, long-term conflict, politics, etc. No one ever threw a chair because there was a facilitator in that space that was encouraging and sort of enforcing acting as a traffic cop to make sure that people were listening to understand rather than listening to like share their experience or jump in with their opinion, etc. 

There are your 3 strategies on how to have and start a difficult conversation. Now, I’d love to share an example of how I started a difficult conversation with my freshman year roommate in college. We got together and I could just tell from the very beginning that we were going to  have some different opinions, we’re going to butt heads. I went downtown to the poster sale. My wife and I and son recently moved and I found this poster crinkled up. It’s kind of gross actually. But I went down to the downtown to a poster sale and grabbed a poster of a big elephant. I pinned them up on the wall and when Ben came back, I said, “Hey, Ben. I’m excited to live with you. It’s going to be an adventure. I have a feeling that we’re going to have some very difficult conversations and moments.

I’d like to introduce you to Jebediah. He is the elephant in the room. I think the more that we point him out, the better off we’ll be.” Surprisingly, I didn’t know this at the time I didn’t have this language at the time. But it was a really practical way to move from content to process. Point out the elephant in the room. Even if you want to share this story, this moment, this idea with a person that you have to have a  difficult conversation with to say, “Hey, I’m just  going to own. Here’s the dynamics on the table. Let me talk about and point to the process.” Really disarming way to shift from content to process. Hope this helps you point out the elephant in the room. If you’re curious to learn more about these strategies, we write about them. 

The book Ask Powerful Questions has a whole bunch of really practical tools to be able to create more meaningful conversations in a difficult context. Feel free to pick up the book.


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